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David Bashevkin: My Dating Story – On Religious & Romantic Commitment



This episode was sponsored by Jerry and Esther Williams in honor of 18Forty and Shalom Task Force. 

In this episode of the 18Forty Podcast, Dovid Bashevkin dives deeply into the world of dating. As we explore the realm of relationships, Dovid uses his own journey to help us find the proper framework for balancing one’s romantic, religious, and professional identities.  

  • How can one stay connected to their religious self while simultaneously evolving?
  • What’s Dovid’s best advice for dating and marriage?

  • Why are we afraid to commit to no?

  • How can we ensure that the years ahead are the best years yet? 

Tune in to hear a conversation on love, commitment, and commitment to commitment. 


Shalom Task Force

The Orchard: A Novel by David Hopen 

Tehillim 27:10

Evolving Religiously During Singlehood” on Singled Out Podcast by Zahava Moskowitz


Garden State

Dovid Bashevkin on Twitter

Spending the Seder Alone” by Dovid Bashevkin

Solitude, A Philosophical Encounter by Philip Koch

Cast Away

18Forty – Rav Moshe Weinberger: Can Mysticism Become A Community? 

Bashert: My One and Only?” on YUConnects CandiDate Podcast

The Paradox of Choice” by Barry Schwartz

The Howard Stern Show: Actor And Comedian Aziz Ansari Visits The Show

Signed, Sealed, Delivered” by Dovid Bashevkin

David Bashevkin: Hello, and welcome to the 18Forty podcast, where each month we explore a different topic, balancing modern sensibilities with traditional sensitivities to give you new approaches to timeless Jewish ideas. I’m your host, David Bashevkin, and this month we’re exploring dating, relationships, commitment, all the good stuff. And I am so excited to announce that this episode was sponsored by my dearest friends Esther and Jerry Williams in honor of, they wrote, David Bashevkin. I’m going to leave that part out. But really, in honor of all those who support Shalom Task Force.

Shalom Task Force is an organization designed to combat and prevent domestic violence and foster healthy and safe relationships and families. Their annual breakfast is Sunday, December 11th, where they have been kind enough to honor 18Forty and the work that we are doing. I will certainly be there. I hope some of our listeners will be there. And please check out the Shalom Task Force website to find out more. That’s Shalom, S-H-A-L-O-M,, where you can hear more about their upcoming breakfast and all of their incredibly important work.

So thank you so much to our friends Jerry and Esther Williams for the sponsorship of this episode. And the irony of them sponsoring the episode about my dating story I hope is lost on no one, but I can only guess will be lost on nearly everyone. This podcast is part of a larger exploration of those big, juicy, Jewish ideas, so be sure to check out That’s one, eight, F-O-R-T-Y, dot org, where you can also find videos, articles, recommended readings, and weekly emails.

I feel like I’m always making a disclaimer that I’m nervous about the topic that we’re about to do. I’m nervous about this topic, but not because I think we’re going to accidentally say heresy. I don’t think that’s going to come up. I’m nervous about this topic because it is uncovering wounds that I haven’t really thought about, thank God, in quite some time, haven’t really done a really deep dive in them. I thought it was absolutely necessary to resurface and really think about a certain period in my life that still in many ways shapes and animates who I am today, and that was the period in my life when I was dating.

This series, in one sense, is about dating, about the struggle of being single, and what individuals who are looking for love and commitment in their life can do, and also what we as a community can do to make that journey a little easier, but that’s really not, in my mind, at the center of this series. At the center of this series is the question, as we’re phrasing it, relationships and commitment. Because I think, more than anything else, when I tried to go back, and I very much did, before recording this, before preparing this, I did a deeper dive than I ever expected myself to do, and really found parts of myself that I haven’t thought about in ages. But some of them were strange and unfamiliar, but some were deeply familiar. Because I think at the heart of the difficulty of romance, the difficulty of commitment and relationships is actually very much a product of modernity, and that is going to shape this entire series.

And that is, one of the great features of modernity is access to choice, is access to choice in communication, in travel, economic choice, professional choice. And normally we think of choice as this great springboardto finding what we want. We have access to more, it is easier to find what we want. And in many senses that is true. Optionality gives you more variety and allows you to really look at the entire gamut of possibilities and say, “I could go into this profession, I can go into that profession, I could live in this community, I could go to that community.” Any major decision that we want to make in our lives, we essentially have this plethora of choice or plethora. I just got a voicenote, which I very much appreciated, it said that I may be mispronouncing the word plethora. I think it’s plethora and I apologize to all our listeners. It was not Mel Barenholtz who normally calls me out on these things. It was somebody else who reached out to me about that pronunciation. But be that as it may, we have so much more choice in this world.

So in a sense you would think from a distance that modernity and the choice that the modern world brings makes it easier to find what we want. And I think that one thing about commitment and about finding commitment in our lives is that choice in many ways makes it more difficult to find what we want. You could imagine somebody growing up in a village where they’re like a dozen families that you could have a romantic relationship with their children or whatever it is. There are maybe three or four professions that Jews are allowed to go into. I’m not waxing romantic about all of the antisemitism and the economic hardship that that world brought, but that world, in many ways, it was easier to foster commitment because there was less choice. In a world where we can fashion ourselves any way that we want, we can become anything that we want, very often fostering commitment in relationships.
And when I say relationships right now, I’m not even talking about romantic relationships. And that is really a thread throughout this series, is that the struggle for romantic relationships, and Lord knows it is a struggle, is really something much broader. It is fostering a sense of commitment in our lives that we’re able to fall in love and build commitment with ourselves, with our community, with our professional lives, our family lives, our romantic partners, et cetera, et cetera. And that is a struggle that I have had throughout my life and something that I’ve spoken about in previous interviews and something that I have written about. And I thought to open up the series, I would share my own story.
Now of I of course am not going to go through the deep dive in this story and start naming names of all of the people who wounded me. God forbid, I am grateful to everyone, really grateful to everyone in my story. And recently have had some really, really powerful conversations, really real conversations that I am so grateful for from I would say people from my past, but people who have been with me throughout, who know who I have been throughout. Because I think there’s something about, I don’t know, late 20s, mid 30s, there’s something about life. I think maybe the way I would phrase it is when most people around you on a day to day basis don’t know anything about your childhood, they’ve never met your parents, they’ve never been to your childhood home, and you go about your day to day life and the closest people around you, your next door neighbors, the community that you belong to, your colleagues, even your spouse in a lot of ways, they never knew the world that you emerged from.
And it could feel like alienating. You could feel in some ways that adulthood brings about this sense of self where you feel alienated in your own life. And I know a lot of people who have struggled with this, I struggle with this. I think it’s something very normal and very natural. And I’m very grateful, and I think one of the great blessings that I have is that I remain connected to my childhood friends who have known me throughout this process and are able to kind of answer the question when you look at your life. The question that my sister famously posed to me during one of my weaker moments that sent me to an absolute spiral, I think she was referring to my professional life, she said, “David, is this what you had planned? Is this the life that you chose?”
And you could be stuck in the middle of your life, in the middle of a marriage, in the middle of your professional life, and those questions can bubble up because you feel in many ways like untethered from the person who made these decisions originally, from the world from which your life emerged from, your childhood, your teenage years, maybe your early twenties. And for me, when I think about this series, at least to begin with, and my own dating story, my own story of dating is really about reconnecting and confronting for a second time that person and what I went through. I’m using the third person he as if it was a separate person. But what I went through. But in many ways it does feel like a separate person, to reimmerse myself in the pain and the loneliness that goes through on the journey towards commitment in any aspect of your life for me was incredibly jarring, because as I’ve said before, I got married when I was a little bit older.
And this is an important disclaimer, again, this is so much more than dating and that’s going to be a mantra throughout this entire series. But the second disclaimer is that I was a little bit older when I got married. But when people find out how old I was, they’re kind of like, “Come on now. You don’t have the right to complain and kvetch. And in some ways they’re right. When I look back, I was 29 when I got married, it felt to me like I was dating for decades, plural. And looking back, thank God I got married. I’ve been married for close to 10 years and the most joyous, most edifying, most inspiring part of my life, undoubtedly it’s at the center of my life. But when you date for a long time and you’re looking for that alignment in your life, whether it is your professional life or your romantic life, and you’re looking for it to set up, until it does, that loneliness, that isolation, that inability to imagine the situation ever being resolved stays with you no matter what.

And my difficulty with commitment itself does stay with me in my professional life, in every aspect of my life. You’re always grappling, you’re always thinking what else? What if? Questions that of course we will get to. I wanted to begin the series with my own story to know where I was coming from and short of naming names and taking you through a story that really is worthy of a memoir, I was having a conversation with somebody who probably knows more about this story than anyone, though I’ve never really spoken with him directly, and he compared it to a book that he actually found about on 18Forty with David Hopen, who’s the author. The book is called The Orchard. And we had David Hopen on here and he tells the story about modern Orthodox kids who have this moment of The Orchard, which he takes from the Talmudic story of the pardes where these different rabbis go into this mystical orchard and have this moment of self discovery or self alienation.
And he reached out to me and said there was a moment where we as friends, as people who grew up together, like we had an orchard moment. And he realized, and actually he’s a hundred percent right, I actually in this interview with David Hopen actually made reference to the fact that I think in my own life I had an orchard story going into this remote place in my own life, in my own sense of self, that really fashioned me. And I think that is my story of dating, which really shaped the person who I am today. It shaped the way that I think about commitment, the way that I think about life, and the a way I think about fashioning your very own sense of self.
And I wanted to begin, and this is a jarring way to begin, we sometimes begin by reading emails, by reading anonymous letters. To prepare for this series, I went back and read old emails that I had with people who were involved in my dating life. I have a file in my computer where I saved a lot of letters that I didn’t even realize that I still had. And one document I had, and I remember writing it now that I saw it, but I didn’t remember seeing it, but it was called, “This Is A Memoir.” I read the writing and thank God it was written, it says the date last modified as November 30th, 2008. So this is well over 10 years ago. I’m in my kind of mid 20s I guess at the time. And I opened it up to see what was there. And I wouldn’t call it a memoir, it was kind of like a self-reflection. I don’t even know if I would call it a diary.
Maybe I thought I had ambitions of publishing this one day. And honestly, I’ll be real with you, I do have ambitions of sharing this story one day because I think it’s a story that’s much more than dating itself. I’m not going to read what is in here. It is really jarring for me to read now. And anybody who’s ever gone back and read old emails and old texts, whether a week later or years later or certainly over a decade later, there is something, I don’t know, sometimes it feels cringe to read it and be like, oh gosh, did I really write this? I was really moved. I was really moved to read what I was going through and how I articulated how painful it was. But that’s really where I wanted to start because this story for me was really painful and it is powerful for me at least and hopefully it’s instructive or it resonates in some way when you listen to it.
This is written before I had published anything, before anything. I wrote a book on sin and failure before I made this kind of my cutesie brand. I read it and I was like, wow, this is the crucible. This is the struggle from which I emerge. And I want to read the opening paragraph and the final paragraph, you know it stops in the middle, and share with you what I was going through in 2008. It begins as follows.

“This is a memoir of failure. I’m about to finish what seems to me to have been the hardest year of my life. All of my friends are married. I am not. I am lonely and embarrassed. I am not embarrassed just because I am not married. There’s a lot more to my shame and embarrassment. Let me explain.” And I talk about what I was going through and what I was struggling with. Religious difficulties, life difficulties, disappointments. And I conclude with something that is fairly raw. It seems almost like a letter. It’s dated. It doesn’t quite seem like a diary to me, but this is the final entry in this thing that I wrote.

“Now I’m not as angry as nervous. Nervous for what I have been nervous for all along. Maybe I will be alone forever. Will I ever find that person to share myself with. Ki Abba v’Ima azavuni, Ki Abba v’Ima azavuni, which just to be clear, I didn’t source it, but that’s a pasuk in Tehillim, in perek kaf zayin pasuk yud, chapter 27, the 10th verse. And it says “Ki abba v’Ima azavuni v’HaShem ya’asfeini“, my mother and father have left me and God should gather me in. And I wrote, I love my parents so much but I cannot connect to them anymore in the way I did as a child. I am no longer a child. I have to face my own problems. But here I am lonely as a child, more alone in a sense. I feel godless and homeless. My home is turning into a house and my God feels distant and I don’t have the strength to find Him. But He has the answer for this darkness. Only He has the switch. That thought sometimes gives me hope. Sometimes it just makes me angrier.
Why don’t You?” And here it seems that I’m addressing God. “Why don’t You just turn on the light already? There’s so much hurt, so much anger. How does this relate to Your glory? So here I am, sleepless and tired, but when I close my eyes for the next day, I’m just faced by the weight of my fears and my future. Will I ever find her? Will I ever return to Him? When I talk about my problems, they think I am whining. They’re not as glamorous as others but they hurt just the same. When I look at everyone else, it seems they were given the strength to get through their pain. I don’t have that strength and I was weak even before this all started. I’m just broken now and waiting. I want to have the strength to be happy for other people. I want the strength to show my parents how much I love them and how much they mean to me. I want to be able to thank all my friends and for getting me to where I am today. I want to get where I want to be, but it’s been more than weeks or months, it’s been years, and I’m still talking about the same stuff. Choshech, yerida, michsholim, when will I have the opportunity to speak about the good stuff? I want the good stuff. Now the anger seems to have passed and it’s just sad and lonely. I want to be happy and tell the whole world how great life once was and can be. Please, please, please let this end. I know life will always have its ups and downs, its nisyonos, [which means struggle]. But I want a new nisayon, I’m sick and tired of this one.
I’m going to wake up tomorrow morning. I hope I feel You, referring to God there, waiting for me. Because without you waiting, it’s hard to show up. See you then, lonely, sad and waiting. Love, Dovid.”

It is pretty hard for me to read that. I think the parts that are the hardest is the desire to want to show gratitude. I wanted to bring nachas to my parents, I wanted to bring nachas to others, which is probably part of the pathology of being almost alienated from myself and wanting to please others. But I think it came from a very sincere place also of just like I don’t want to be everyone’s problem. I don’t want to just be “How’s Dovid? What’s going on with him? Has he found his way yet?” As I wrote, I want to have the strength to be happy for other people. I want the strength to show my parents how much I love them and how much they mean to me.
And when you feel so overburdened by indecision, by any pathway forward, by a future that looks pitch black, at least in my own eyes, you don’t have that capacity. And finally the thing that really haunts me, and that I still think about, is I know life will always have its ups and downs, its nisyonos, but I want a new nisayon. I wanted something else to think about. I wanted something else that was at the center of who I was and shaping me into who I wanted to be. And I think this letter, this writing, this memoir, whatever it was, whatever it was meant to be, and I’m sharing you now, because it was meant to be something and I feel like I’m giving my younger self some life and purpose by even being able to read it now. I think this is the self that I emerged from and it’s that self that I spoke about in conversation with somebody named Zahava Moskowitz.

Zahava Moskowitz is one of my first students. She barely remembers, I ran a class in Long Island University and she ran a podcast called Singled Out and she interviewed me. Singled Out was for people who were single, who were dating. She interviewed me to discuss religious evolution while you are dating. And to open up this story about my own dating and my own life, I wanted to begin with this conversation that I’ll provide commentary for. And I want to apologize, it’s such a shame, I re-listened to it, I think everything that I shared is something that still resonates and something that I very much would share again today. My only apologies to our listeners is the sound quality is not what it should be. I recorded it via Zoom, I didn’t do a separate recording on this mic, so my apologies for that. And I assure you in our later episode when I reflect directly with Zahava about her project of Singled Out, we use much better mic equipment. But without further ado, and with that kind of introduction, I wanted to share the opening of my conversation with Zahava Moskowitz on the Singled Out podcast.

Zahava Moskowitz:
Hello and welcome to Singled Out, a podcast where we discuss the difficulties of being single in the Jewish community, as well as ways of making the most of it. I am super excited to have with me David Bashevkin. Welcome David to the show.

David Bashevkin:
Zahava, this is so special. A, talking with you, and talking particularly about this issue, which I feel like I’m losing credibility on, cuz bli ayin hara I’ve been married years already. But my experience dating was one of the most formative and important journeys. It has enduring effects on how I look at the world, how I build my current relationships, so this is really a-

Zahava Moskowitz:
You’re saying even posting? Go ahead.

David Bashevkin:
Yeah, exactly. For me it felt very long. It felt like eight years, it felt like a long time. And a lot of times you imagine that you’re going to turn over this chapter and start fresh, like okay, now I’m married, and those wounds, that grit, what I describe as almost like calluses, like a musician has on their fingers, these calluses that you develop on your fingers because you’ve been playing the instrument for so long, just disappear. That is very much not the case.

Zahava Moskowitz:
I guess if you can just start us off, give us some background, if you don’t mind, into your experience with singlehood and with dating.

David Bashevkin:
Yeah. Zahava, you don’t have to edit this out, but we’re speaking about marriage and family life. My son is calling to me, he’s not yet in camp yet, I have to wipe his tush. So you don’t have to edit this out. I’m giving you permission.

Zahava Moskowitz:
This is real life parenting 101.

David Bashevkin:
Listeners know what this life is, but give me 10 seconds.

Zahava Moskowitz:
No problem. Take your time.
Okay. Brief commercial break, and we’re back. Before you were married, I guess when you think back to that time, what are some of the things that you think about and what was that experience like for you?

David Bashevkin:
So I evolved a great deal from when I started dating, both in terms of the community that I found that I was kind of situated in and where I wound up. When I began dating, I was a student in Ner Yisroel, I would wear a black hat on dates and a suit sometimes, not always. And I was going out with either very frum modern Orthodox women or open-minded yeshivish. I left Ner Yisroel two years after I started dating and then I went to Yeshiva University and started dating there. And by the time I got married, I know I’m describing this evolution based on the clothes I was wearing.

Zahava Moskowitz:
That’s okay, no, we’re getting a sense religiously.

David Bashevkin:
To me it was a big part of the evolution. I was going on dates wearing good dating jeans, a sports jacket, a little bit more different. And I definitely evolved religiously, I think I evolved in my personality, and I had this ominous feeling when I started dating that this was not going to go quickly. It was an ominous feeling.

Zahava Moskowitz:
Interesting. Even at the start you felt that?

David Bashevkin:
I knew it right away from the start. I knew it right away from the start. I knew this was not going to go quickly. There was one person who I wanted to get married, kind of like a person who I grew up with, and that did not work out, and that knocked me out emotionally and religiously for many, many years. I think a lot of people have the relationship that they’re like, okay, this is the one that has to work or I don’t know who I’m going to marry. I’m going to be bereft. To be like, you’re really on your own. And I had such a person and it didn’t work out, and I even knew before that it was not going to be so simple for me. I knew that right away.

Zahava Moskowitz:
Interesting. I’m curious, is that because of your personality you knew that you’re maybe just more complex or different or more out the box or just in general kind of had this feeling?

David Bashevkin:
I think my expectations were too high. Not for the girl, not for how pretty she was or how smart or family, all those things that we put on. I think my expectations were too high for what this relationship was going to do for me or what the feelings were going to immediately provide for me. My rebbi, Rav Ezra Neuberger, one time told me, this is something that’s always stuck with me, the main focus of teshuva is teshuva on your expectations. That sometimes your expectations are too low and sometimes your expectations are too high. And I grappled with both in my life and I think at that point in my life, my expectations for what this was going to provide for me as an individual were not healthy or realistic.

Zahava Moskowitz:
You mentioned a little bit about how you start to change and how religiously you start to evolve just based on your clothing and more externals. But I’m curious, I guess internally what ways do you feel like you evolved religiously throughout your singlehood?

David Bashevkin:
When I started dating, and I told you there was this one person who I thought I was going to marry, I thought I had to marry in order to just have somebody in my life, anytime I would have a phone call or an update related to this person, I would go into a room and I would say Tehillim. And those calls didn’t always end the way I wanted them to and I found myself saying Tehillim less and less frequently, and I found my ability and capacity to daven in the way that I had when I first began, slowly began to erode and diminish, and it became harder and harder to daven with the same capacity, to have that same sense of hopefulness that I once had. Those text messages, I wrote a column on this for Mishpacha Magazine, the different stages of text messages you get when you’re dating on Yamim Noraim, like “This is your year”, ten exclamation points, and then three years later you’re getting those messages, “I hope you find clarity.”

Zahava Moskowitz:
What a jump. Yeah.

David Bashevkin:
Yeah, it’s like I think I was much more hopeful and optimistic this is going to be my year, my tefillos are going to change this. And I think I had to reorient my relationship to davening itself and, again, creating capacity, that’s a word that I use a lot in the way I think about my own life, capacity to accept that my life did not unfold the way that I thought it was going to unfold. That required for me a great deal of daveningand a great deal of maturation to understand what role davening was going to play in my life.

Zahava Moskowitz:
It’s funny, the analogy my dad used to give us growing up was “Tefillah‘s not a gumball machine.” But I think for a lot of us it’s like we assume, we daven, you turn the nozzle, it maybe gets stuck, eventually it comes out, and then when it doesn’t, it does cause people to waver religiously.

David Bashevkin:
Tefillah for me is when your quarter gets stuck in the gumball machine. And it’s not for the gumball to come out, it’s for the acceptance of the frustration, to have an outlet and a place to put that deep existential frustration. Again, everybody has difficulties and setbacks in their life, but the setback of dating I think is of a qualitative higher order because you see all your friends match off. I always think of that opening scene from Bambi where Bambi’s walking and he’s got Thumper behind him and the skunk, and they all find their lovers, and you see all your friends pair off, you see your relationships with your friends change, that you become the object of their pity, to be blunt. Which is hard. Like “Thinking of you”, “Root-“, “I think I have a-“, and everything starts to revolve around that. And when the whole world looks at you through a certain lens, it becomes very hard to not look at yourself with that lens.
And that lens that you end up looking through is that I am not whole, I am not complete, I am missing, I am late, I am not yet there. All of the words that we use in our heads. And that brings a lot of anxiety over who am I? You feel impermanent. Even those little triggers, the triggers for me was finding new roommates, who am I living with this year? Every Shabbbos became another trauma, so I would just eat by myself on Shabbos. I wrote an article about this. I had a Pesach seder by myself.

Zahava Moskowitz:

David Bashevkin:
Purposefully. My parents were going away. They of course invited me to come. I’m not blaming them. I didn’t want to be a guest in somebody else’s home. I just wanted to be home. And the hardest thing I felt about being single is that the very portrait and feeling of home starts to crumble. God forbid not blaming my parents, that’s such an important relationship to keep intact. But you would go home, it didn’t feel the same home that it was when you were a kid.
You’re supposed to have your own home, and you felt it in subtle ways. And you’d be in an apartment but that wasn’t home either. Like I would, “Where are you going?”, “I’m going home.” What were you talking about? Your apartment that you have a one year lease on or your parents’ house. And the scariest part was that in my heart of hearts, it was neither. Like, I don’t know where home is. That lack of home-ness in your own life can really upend your, not just religious identity but your identity. Who am I? Where do I reside? Where is my home? That bereftness can take a tremendous toll. And it took a tremendous toll on me personally and certainly had religious components.
What I am grateful for, and really the hardest part to talk about, is the intensity of the loneliness that I had at that period in my life. That sense of being homesick in your own home and how my entire life felt impermanent. It reminds me of a clip from the movie Garden State where Zach Braff’s character is talking to kind of his love interest in the movie, Natalie Portman, about this notion of homesickness.

Zach Braff:
That point in your life when you realize the house you grew up in isn’t really your home anymore? All of a sudden, even though you have some place where you put your stuff, that idea of home is gone.

Natalie Portman:
I still feel at home in my house.

Zach Braff:
You’ll see one day when you move out, it just sort happens one day and it’s gone. You feel like you can never get it back. It’s like you do homesick for a place that doesn’t even exist.
But maybe it’s like this rite of passage, you know? You won’t ever have that feeling again until you create a new idea of home for yourself, for your kids, for the family you start. It’s like a cycle or something. I don’t know, but I miss the idea of it, you know? Maybe that’s all family really is, group of people that miss the same imaginary place.

David Bashevkin:
Being homesick in your own home where you look at your own life, so to speak, and you don’t feel like you even have a home. What I wrote in that opening letter that I read from from 2008, my home is turning into a house, where I didn’t feel quite at home in my childhood home. It felt like a house that I would go to. It’s not where I live anymore. And I certainly didn’t feel that sense of home-ness in the apartments I was renting out, though my roommates and those people in my life are people I’m still deeply, deeply close to. But that sense of being alienated from yourself, I think that for me, what I did really poorly in this period in my life, once I left yeshiva, I was living on my own in Washington Heights, we happened to have had a gorgeous apartment on Cabrini Boulevard.
It’s like this wonder list, like this Narnia hidden the middle of Washington Heights. People don’t know about it. If you live in Washington Heights you know about the YU community and you go to the other side, middle there are all the stores, and then you go to the other side and there’s like the Breuer’s, Mount Sinai community. Go all the way up the stairs, there is this magical fairy tale land. I don’t know, I don’t think it has a bustling Jewish community, but it’s where I lived on Cabrini Boulevard. It is gorgeous. It looks like you’re stepping into a wonderland that you don’t see, like the stores are all these, I don’t know, artisanal, fancy coffee shops. It’s really, really nice. And I loved living there, but I hated the notion of living by myself and having to reconstruct myself every year. Find new roommates, find new apartments.
What I one time shared is that my entire life felt like Sukkos. There was a notion, it was very interesting, because Sukkos was actually the holiday that I struggled with most, though I certainly struggled with all of them, I struggled with most when I was single. I couldn’t connect to it at all. And it took me years into my marriage to reignite, to almost become friends with Sukkos again. And that’s why it’s become my most beloved holiday because I know what it means to be alienated from a Yom Tov, to feel like a personal grudge. I one time shared on Twitter right before Sukkos, I wrote as follows, “When I was single, I really struggled with Sukkos. Struggle is a generous term, I wrote, I hated it. My life already felt impermanent. Every year, new roommates, every Shabbos scrambling for meals, being with family when I didn’t have my own was hard. My whole life was already Sukkos. Even my first years married, I struggled to adjust. We went to family and didn’t build our own Sukkot. So much has changed in my life and my relationship to Sukkos and I’m so grateful. But I never forgot about those years when it was hard, when it wasn’t a time of happiness. So if these feelings seem foreign or ridiculous, you have something else to be grateful for. But if this is something you’ve ever felt now or in the past, Sukkos isn’t always happy, and that’s okay. Sending love and blessings that it will be such a time of joy for you very soon.”
Part of the pain for me was that Sukkos was this holiday of joyfulness and it compounded the frustration for me. Like, you don’t just want me to celebrate, you want me to be happy about it? My life is already Sukkos. My life feels impermanent, and I was never able to connect with it.
And I think holidays and Shabbos general during that period of my life were very difficult. I never connected to a single community. I spent countless Shabbosim either by myself or just with my roommates. I never really hosted meals. I even wrote an article one year Pesach, I spent a Pesach by myself. I remember when the lockdowns for Corona happened right before Pesach, I shared an article with Tablet Magazine called Spending the Seder Alone, about the experience of actually having a Pesach by myself. And that notion of having an experience all by yourself and how that shapes you really stayed with me. I mean, you’re really divorced. So much of my life is in the public, sharing now on 18Forty, on social media. But there were periods in my life, and I still nurture and maintain them, because it’s really how you learn who you are as a person, where you have solitude, not isolation, not loneliness, and I think that was part of the pain of this period, but solitude.
And I actually went back to read that reflection I wrote so many years ago about that Pesach that I had even more years ago. I think that Pesach was probably in 2008, the same year that I am writing this memoir that I read from. But I wrote many, many years later, before Corona in 2020, a reflection about spending a Pesach seder by myself when I was single. And I wrote as follows, “Nine years ago, when I was 26, I celebrated my seder alone in my parents’ kitchen. My parents decided to travel to Israel to spend seder with my sisters. I didn’t want to join them. I felt too old to spend the week sharing a bedroom with my nieces and nephews. My mother begged me to find another family to spend the seder with. But if I wasn’t with them, I was adamant that I did not want to be an appendage in someone else’s family.
It was probably most painful for my mother. I didn’t have a family of my own and the thought of me alone in our kitchen broke her heart. I’m nearly certain that she did not even tell my father about my plans. I was more forlorn than anxious. Everyone else was preparing for the festival of freedom. I prepared for an exilic hell. And I wrote about being in a kitchen by myself and asking myself the Mah Nishtana. And I actually made reference to that fantastic book that’s worth reading, called Solitude, A Philosophical Encounter by Philip Koch, which I think all of these questions emerge from that confrontation with self in solitude. And he has something amazing there. He writes, “The mere presence of other people obliges us to coordinate our experience with theirs, thereby diminishing the scope of our actions. As one person’s experience of viewing a painting in a museum changes when another person walks up, our subjective experience is influenced by the slightest interaction with another person.” We spend so much time with other people who shape our very experience, and having moments of solitude, though I certainly wouldn’t wish them again on myself or anyone else, can be moments of profound clarity. He writes, “We become conscious not only of the object we are viewing, but also of ourselves as viewers. When you go up to a museum and you see everybody crowded around another painting, it’s their attention that is shaping your own. Solitude can minimize such intrusive self consciousness by reducing the immediate demands of experiencing ourselves as the object of another person’s thoughts and actions.”
And to me, when I was reflecting on this article about spending Passover alone, I think that really shaped the experience. I wrote, “Single and alone is never how I envisioned my seder. But it did confirm this point that one’s freedom to search for one’s spiritual essence is augmented by solitude. Before I was married, I would make sure to project a sense of confidence and assuredness that internally I really didn’t have. I was nervous, I was confused, I was lost. But I never allowed myself to show it. I may have even convinced myself alone drinking four glasses of that heady wine, I could finally be honest, I could finally be vulnerable. Questions I took great care in avoiding the rest of the year, my career aspirations, my desire for a family, could finally be articulated. This night was different because I was finally asking different questions. The hour into my seder, my solitude grew more comfortable and natural. For moments I even forgot I was alone.
And God took us out of Egypt, like it writes in the Haggadah, not through an angel and not through a seraph and not through a messenger, but the Holy One Himself. God had redeemed alone. My lonely redemption felt more natural. My seder was almost over. Who knows one? I looked around, I knew one. Chad Gadya, one kid goat. I smiled. My seder ended singing about a lone goat finally redeemed.”
And it was those moments of solitude that I remain grateful for as painful as they were. Because I still think today with a family, with, thank God, a life that every moment I’m grateful for, because it wasn’t always this way and I was very aware of what I was lacking and what I was missing and how painful all of that was. But it really shaped who I was. And in a larger sense, it shaped not only my romantic life, but it absolutely shaped my religious life.

I have long said that there is a unique experience of going through your 20s in the Jewish community, where, the way I conceptualize it, it is like this Bermuda Triangle, where we have all of these planes that are taking off and our graduates of all the Jewish camps and Jewish schools and Jewish communities that are fostering this commitment. And then we see the planes off and we wave goodbye to adulthood. And the problem is we are losing a lot of planes. Where are we losing the planes? The same place that I used to read about as a child that we would lose planes, and that is the Bermuda Triangle.
Now, this Bermuda Triangle is not off the coast of Florida forming a triangle where a lot of planes were lost in tropical storms, but there are three points that we are losing a lot of airplanes. And that is, the three points are, our romantic identity, our religious identity, and our professional identity. And when we leave the auspices of the Jewish institutions that have nurtured us and where we’ve grown up, we expect people to resolve these three aspects of their identity rather quickly. We want them to figure out, what are you like? What’s your religious identity? What is your romantic identity? Settle down, get married. And finally, what is your professional identity?
And particularly in the Orthodox Jewish community, we want people to figure all of this out by their early 20s. But the truth is, no matter what part of the community you’re in, what part of the Jewish community or, frankly, even non-Jewish community, I think a lot of people are figuring this out. They’re trying to figure out all these three things, and maybe there are different deadlines, but there is this sense of, “I’m late. I’m late, and I want to figure out who I am by resolving these three points in my identity, my religious identity, my professional identity, and my romantic identity.” And that can be really hard. Those are big questions to resolve and find the path in.

And I think in my own story, I got caught in this whirlwind. I got lost. And as my romantic identity didn’t quite resolve in the way it was supposed to, it affected and brought instability to my religious identity. And that instability in those foundations really affected even my professional identity, where at a certain point I felt bereft and lost. And that self that I felt like I emerged from Jewish institutions, from… I went to an unbelievable elementary school, high school, yeshiva in Israel, yeshiva afterwards. I had all these things that really shaped who I was religiously and provided this incredible foundation, but all of a sudden I felt like as I was emerging into adulthood, everything started to crumble.
As my romantic identity didn’t work out the way I had hoped it would, it absolutely crumbled my religious identity. And my religious identity, when you have all this rubble and the foundation starts to shake, my professional identity got wobbly as well, to the point where who I was as a person didn’t feel stable, didn’t feel that sense of stability and longevity that I think people want to feel in their very own sense of self.

And that’s why to me, the question of dating really goes hand in hand in a lot of ways with the question of religious evolution, religious development, that we leave and we usually begin dating, depending on what community you’re in, your early 20s, mid-20s, whenever it is. And that’s really the same time that you’re figuring out who you are professionally and who you are religiously, what community are you going to part of. And it’s really hard to keep everything intact.
And I think for myself, looking back, and what this next part of my conversation with Zahava Moskowitz was about, was about learning to embrace that volatility and not feel that for the rest of my life I had to somehow, some way, stay who I was when I was 21 years old and remain that way for the rest of my life.

Zahava Moskowitz:
The biggest change, I hate putting it this way, I think is people tend to become more modern or give up certain things religiously during that time period. So I guess I’m curious what you feel like are the defining factors, what contributes to that?

David Bashevkin:
I want to first make one important disclaimer. You absolutely should and will evolve religiously after you get married. I think that now that I am married and I see myself continuing to evolve religiously, I can better appreciate the religious evolution that I had before I was married. And I deliberately use the word evolution because I think that, assuming most of your listeners went to a modern Orthodox elementary school, high school, to seminary or yeshiva for a year, you have this feeling of like, “Okay, I am who I am. Now that I’ve left seminary or yeshiva, I need to keep this intact until I am married. And now once I’m married, then I could kind of let all of these cumbersome packages that I’m holding, I could set them down on the counter.”
But this whole time through, you’re holding these massive packages of what it means to be frum and all of the expectations, I let down one of the massive grocery bags, then I’m not going to wind up with the person who I’m supposed to be with. I want to end up with the person who’s usually either reminds you of your father or mother. Not to get Freudian, but let’s be real for a second. Religiously, you want to get back to that a lot of times, the person who goes to minyan every day, the person who has the Shabbos table that you grew up with, and the Sukkos, and Yom Tov, and all of this stuff. And you’re holding all of these packages in your 20s and you’re like, “I don’t know where to set these down.”
I did set down a lot of packages and a lot of areas of my religious life did evolve. And I frame my evolution not as a deterioration, but as a sense of rachmanus that I had on myself, of self care, of being gentle with myself and the expectations that I allowed to be placed on myself. Which doesn’t mean that I threw everything out the window. I use this analogy a lot. There’s this movie that I absolutely love, called Castaway. And there are a lot of beautiful analogies from that movie, but it always resonated with me, A, he’s stuck alone on a desert island. Which, before I was married, it resonates with you. He’s got this volleyball that he becomes friends with-

Zahava Moskowitz:
A little too friendly, yeah.

David Bashevkin:
Yeah, your friendship circles, the way you occupy your time, it’s different. It’s about learning how to be comfortable on your own.
But there’s one thing that always moved me in the movie, which is that he was on an airplane that was a FedEx airplane. And he opens up all the packages to see maybe there’s something that could help him get off the island, except one package. He leaves one package unopened because that also served a purpose for him as he wants to deliver it back once he gets off, because, “When I do finally leave this island, when I do find myself in a different place, I can take this package and give it to somebody else.”
To me, I think there’s a religious analogy there that I think religiously we open up a lot of the packages that we’re holding “till I get off the island”. And I’m not going to tell your listeners or you which package that could be. My package was my relationship with Torah learning. So for me, davening in a minyan was a trigger. It was very hard. That’s very male-centric. Because most married men wear talleisim, and I felt like I was announcing to the world that I am not yet married. And I found it really hard to daven in a minyan as I got older and older. As opposed to going into a beis medrash, there felt to be like there was this sense of equality that if you’re here, we don’t care what you’re going through or what your background is.
My recommendation always is to leave a package unopened. And I kept that package with me through some really… There was a lot of broken and frayed Amazon packages surrounding me, but I had rachmanus to open up packages and I also had the commitment and resilience to have a package that, “I want to take this with me off the island. It means too much to me to let go of.”

Zahava Moskowitz:
First of all, I really like that analogy. It has been a while since I’ve seen the movie. And of course, now I’m like, “Oh, I should watch it again now with this new lens,” but I think that’s a really, really poignant and deep analogy to make that comparison between how we deal with things when we are single, when there are all these different religious factors. And it sometimes feels like it’s not so sustainable because I don’t have so many places to put it necessarily, and I can’t just plug it into a family lifestyle the same way other people can.
And I really appreciate your outlook that it sounds like basically the theme is to just try and be kind to yourself in that process of changing and evolving. I guess my question is, what recommendations do you have to still stay connected? So is it just leaving that one thing sacred or one thing that you connect to alive? How do you maintain that connection?

David Bashevkin:
It’s a hard question to answer because it varies so much.

Zahava Moskowitz:
Yeah. It’s individual, for sure, yeah.

David Bashevkin:
People… And one person’s trigger can be another person’s salvation. I think that as you mature, and this is rightfully so and doesn’t end after you get married, your emotional health and your religious health need to align. Because of our own immaturity as we’re growing up, we don’t always figure out how to align those two and how to put ourselves in emotionally healthy situations that also align religiously. I think when you’re single, again, for myself and for a lot of people, it’s having a good group of friends. When I say good group of friends, I don’t mean the shtark crowd.

Zahava Moskowitz:

David Bashevkin:
I think a lot of times that could be unhealthy. That wouldn’t-

Zahava Moskowitz:
You mean like supportive people?

David Bashevkin:
Yeah, supportive people. People who you feel like you’re you with instead of not yet married, instead of are you dating, are you busy? All those things.
And for me that was some of my married friends, like my old ones from elementary school who I stuck with, I’m blessed to have. But people who I picked up later, a lot of people’s wives, I couldn’t stand them. I couldn’t stand them. We don’t know one another. Spouses were triggers for me because they would take liberties that their husbands had because I grew up with your husband. You don’t have the same liberty to call me up and ask me about my mental health, or are you really happy, or all of these things. You don’t have those liberties. And I would not talk to them. I would not pick up their calls. I insisted on my emotional health because I knew if I didn’t have that emotional health, I would not be able to have any religious health.
They need to align. And at some point in your life you need to make choices. For me, it was buying a pair of jeans, which I did horribly. I think the first pair I bought was from Banana Republic. When I came into there, it was like one of those scenes from a movie, where minors are trying to buy beer.

Zahava Moskowitz:
And it’s very obvious you don’t know what you’re doing.

David Bashevkin:
No, I mumbled to the cashier, I’m like, “So where do you keep the jeans?” I tried to keep it casual. I thought I was going to get carded or something, right? And they didn’t fit and it wasn’t right, but I wanted to rebrand. I wanted to feel like I wasn’t just an older yeshiva boy. I didn’t want to feel that way anymore. So I wanted to dress the part.
You’re not a 20-year-old fresh back from seminary anymore. And feeling that sense of dignity in who you are, I think, is a healthy part of evolution. And just because the community you came from when you were 20-years-old would frown or look at that transition as like, “Oh, we knew this would happen. This isn’t good,” but learning to develop that inner sense of identity, that I define who I am, I have that comfort. And at the same time having friends and mentors who you can talk about these struggles with and you can guide them through, that’s healthy.
I think we can’t spend the rest of our lives looking back at two or three years of our religious development, and just looking at it with nostalgia, and trying to figure out, how can I recreate those three years when you were in seminary? That’s not healthy. That needs to stop. Your best religious years should always be ahead of you.
I am 36 years old. I am more religious now, in the true sense of the word, than I was at the peak of my yeshiva, and I loved yeshiva. I look back fondly at yeshiva. You don’t need to look at it with cynicism; it’s the opposite. You become cynical when that becomes the only model and everything else you do for the rest of your life is undermining those two or three years. But if you learn that those years were a foundation, now I’m building off of it and evolving further, you’re healthier.
Every year you become more religious. You reorient what is, so to speak, in your kodesh hakedoshim, those intimate private moments where you’re actually with God. And figuring out what that kodesh hakedoshim is when you are not yet married, when you are not yet in a relationship, and hewing that out and figuring what do you bring in there, what’s your aron, I think is a really important question and something that a lot of people in marriage don’t have the liberty or luxury to have to ask themself.
And even when the answers may not cohere with who you are when you were 20 years old, have rachmanus, resilience, and the strength of character to really whittle down your values and say, “This is important to me, and this is not as important to me anymore,” and that’s okay. It’s okay that it once was and now it’s not. That’s okay. You could be a good person. You don’t need to be frozen and ossified in this religious carbonite thing like Hans Solo, Star Wars reference. I don’t know why that was necessary, but here we are.
Keep evolving; that’s healthy. You’re not moving farther away from yourself in seminary, you are moving closer towards who you can become with the full embrace, the emotional self-care, and the rachmanusneeded to become a healthy religious person.

Zahava Moskowitz:
There’s so much that you said there, David, that I really, really appreciate and I’m just trying to process. I think that was really, really well said. And I really love the way that you phrased those years or the times where we do feel like we are changing and evolving as a platform as opposed to, “Oh, that was a bad time or when I was less frum,” as opposed to viewing it as like, “No, that’s just a springboard and I use it to grow from, and I’m always changing and growing.”

David Bashevkin:
And even when that doesn’t cohere with that neat stories that we get in yeshiva and seminary, like got married at 22, moved to Ramat Eshkol one year, then came back, took the LSATs. That’s a great story, andkol hakavod to everybody who was able to live that story, but that story is not everyone’s story. And other people have trickier and messier stories and they’re just as religious, they’re just as good, and they’re just as decent.

Zahava Moskowitz:
My one caveat, which I’m curious to hear your thoughts on, that’s coming up for me when you’re saying that just from being in the dating experience is, again, we’re always evolving, but if I’m in a place where I know I’m putting down more of those packages now because I’m not married, dating is also going to look different in terms of who I’m dating and who’s willing to date me, even if that’s not where I necessarily want to be more long-term. Do you know what I’m saying? So I’m curious how you’d approach that.

David Bashevkin:
I don’t know if you listen, I’m going to shout out my podcast. I have a podcast called 18Forty, it’s one, eight, F-O-R-T-Y, dot org, and I had an interview with Rav Moshe Weinberger. And I began my interview by recalling a story that I think relates to this question a lot. Rav Moshe Weinberger called me up to redt me a shidduch.
I respect him a great, great deal. I’m not one of his close, close students and I didn’t daven in his shul, but he knew of me and he called me up, I was in YU at the time, and said, “David, do I have a girl for you!” He went on, “yiras shamayim and the middos.” I could tell, she wants to build a… The whole spiel of that girl who’s fired up. And I told him, and this was the hardest thing for me, but it was healthy, I admitted to him, I said, “Rebbe, I’m not there anymore. That’s not really what I’m looking for. It’s not really where I am.” And I remember his response. He paused. He says, “Ein chassidus k’chassidus rishona.”
The chassidus, the sense of commitment and religious excitement that you have initially, there’s nothing like it, it’s something very beautiful. But what is also implied in that, and I think that much of my interview revolved around this, was that there’s chassidus rishona and chassidus shniya and shlishis and revi’is and chamishis. We oscillate and we come back, and that’s okay.
And when I admitted to him and told him that I wasn’t where I was, because I wasn’t dressing in that same way and I wasn’t the yeshiva guy that I once was, that was an okay admission. You don’t need to announce it to the world, but you also need to be honest and maybe ask yourself that what you were once looking for religiously, that part of the resume, maybe it’s phrased, or maybe your conception of what it needs to be, it’s phrased a little too narrowly, you’re wound up a little too tightly around these key markers of who I’m going to end up with. You don’t need to do that initially, like chassidus rishona, but maybe that’s healthy when you get older.
I know for myself, and my wife and I say this all the time, we would not in 100 million years have dated one another. She was not religious enough for me. And as I got older, my description on the religious component of dating began to get briefer and briefer until it almost disappeared entirely. I’m a big believer in my religious description of the spouse was the personality description.
And I get calls on a lot of people’s resumes, where parents are calling me up asking about men and women. And they’re asking questions that make sense when you’re 20, but I’m like, “This person is 32. They’re 28. Your religious questions need to evolve.” Mom calls me up and says, they’re asking because I’m on somebody else’s shidduch resume, “Does the boy have a relationship with a rebbi?” And I’m like, “Does any 32-year-old? What does that mean? Do I? I don’t know. I’m not calling my rebbi every day.” It’s a conception that you have when you’re younger and you’re in yeshiva, but cut somebody some slack. Cut them some slack, Ribbono Shel Olam. I’m like, “That can’t evolve, what it means to have a relationship with a rebbi when you’re 33 and when you’re 23?” It should evolve.
And when you’re dating, that self-admission that you’re no longer the same person religiously, it can come at a cost, but it could also come with great reward. It could be liberating. You don’t have to announce everything, but there are things that, again, you present differently. That’s healthy. Admit it. Admit it. That’s fine. I’m looking for something a little bit differently.
I still want the Shabbos, I still want the Jewish home, but the ingredients to get there evolve as you date longer. And if you’re 28 years old and you’re still looking for a 22-year-old yeshiva boy, that’s a problem. You have to reorient your thinking of, where would that person be at this point in their life? What would they look like? When you enter into a relationship, let’s see if we can have a conversation together about what our home will look like. There’s something very beautiful about the fact that there’s more maturity and more honesty that you can develop together about what your religious home is going to be, a conversation that’s more or less meaningless when you’re 22 years old. You have no idea what that looks like.
The next part of our conversation was probably the most controversial and really came from my own personal experience. I remember, there was a specific person who I wanted to date who was super duper frummy. She was really fresh out of the oven. I mean, it was very intense. She really had these very admirable and beautiful commitments to Yiddishkeit, and I was at the low point of my religious life, which ironically, in almost like this tragic comedy, was when I was enrolling in semicha. I think that’s true for a lot of people; the low point of their religious life was when they’re not in the beis medrash and learning anymore, but they’re now in a semicha program. They’re in the program now and you feel that escalator bringing you to a particular destination.
It was an absolute low point in my religious life. I was very interested in going out with this one girl, who she was concerned about my religious life. And honestly, she was probably right to be concerned, and she sent somebody after me. That’s making it sound really mean. But she sent somebody after me. I said it again so maybe that’s exactly how I felt. She had me speak to somebody who she considered a mentor to kind of gauge what was my religious life going to be like. And he called me up over the phone, I was in my early 20s, and he started asking me like, “Where do you plan on sending your kids to school? What’s your future going to be like?”
And I remember kind of being very frustrated by the questions he was asking me. I happened to know this person. I was very close with his sister in high school, who actually, this person’s sister, married my mussar chavrusa when I was learning in Yeshivat Sha’alvim. You can guess who that is. Any good guesses should get in 18Forty specially branded prize if you can figure out who this is. I’m not going to give you a hint of what her screen name was in high school. I’m not talking about the person I wanted to date; I’m talking about the person whose brother was calling me up and asking me all of these questions. Her birthday is December 29th, I think. That’s the only hint I’m going to give you.
But anyways, this person, who I knew for a long time, her brother called me up and said, “Where are you going to send them?” And I was hurt. I was hurt in that I felt like I had to figure out the rest of my life in order to be deserving of going out with this particular person. What’s an interesting postscript to this is that this person also evolved a great deal in her own life, the person who I wanted to date. Thank God, we are both happily married. And really, I’ve seen her since then, I wish her only the very, very best. That’s one of the blessings that I have is that when you really are able to build a life for yourself, like in that original letter that I read, you really build the capacity to have joy and happiness for everybody in your life, even if at that moment it felt so painful.
But I remember that sense of, “Okay, I need to figure out everything of what’s going to happen for the rest of my life. There’s some mystery. I don’t know where I’m going to send my kids to elementary school. Give me a break.” And I think that informed the next part of this interview with Zahava, which actually got a little bit contentious about the notion of being growth-oriented in dating. And listening back to it now, I still feel, I think, the same way, but I don’t think I had enough context in what I thought in my own dating life that term was often being used for.

Zahava Moskowitz:
So that’s what I was going to ask you, because I hear the nuance and I think that is so important. But I do think if you’re someone that’s growth-oriented, you do want to make sure that that is in place, even where you are and where your prospective spouse or person that you’re dating is. So I guess that’s a discussion that you have of just like, “We’re both here right now, but let’s talk about what it’s going to look like together.” Because I think it is sometimes a hard line to straddle, where if I’m dating someone that’s in the same place as me, but I still want to find someone that isn’t content necessarily.

David Bashevkin:
I know this is a popular term, and you’re going to not like this, and I want to be careful the way I phrase it. I don’t like the term growth-oriented.

Zahava Moskowitz:
Okay, tell me why.

David Bashevkin:
I don’t know. I think it’s a euphemism for something else. It’s a euphemism for, “I’m here now, but I don’t want to be here.” It’s a harmless term. I don’t think that’s how you were using it necessarily, but when I hear it, and we’re being honest with one another, I get suspicious. I get suspicious that we use the term growth-oriented as a cover for being honest of where we are right now. Meaning, is it a referendum? Is it like, “I heard that you don’t go to minyan every day, but are you growth-oriented?” Meaning, “The moment we get married that goes out the window.”

Zahava Moskowitz:
No, for sure. And you’re right, that’s not at all how I meant it. I like it because it’s vague. See, I think growth-oriented means different things to different people. When I personally said, it’s not targeting specific action, it’s more of, is someone always looking to grow closer in their Yiddishkeit, in their connection to God? And that’s going to be different for different people in terms of what connects them.
So are you someone that’s saying, “This is where I am. This is what Shabbos is for me now. And I’m kind of fine with this being here,” or is growth-oriented, “No, let’s always find ways together to enhance that in our own terms, however we decide that’s connecting us”?

David Bashevkin:
I’m not convinced. I’m unconvinced. I don’t like your use of the word complacent. I’m not convinced. I think you need to fall in love with an individual, with a person, who you appreciate their religious intuition to be able to-

Zahava Moskowitz:
That sounds so much more broad to me. How would you define religious intuition?

David Bashevkin:
It comes from a place of trust of where we are now. It comes from a place of trust that doesn’t need to be spoken out about what’s going to change after we get married, because I have trust in who you are religiously right now. And I have trust that because who you are right now in this very moment that I accept and I appreciate and I am trusting of, I know we’re going to evolve. I know things are going to be different.
And I sometimes feel that growth-oriented or complacency is a distraction from your ability to have that complete trust, to have that complete trust that you as a person now and your religious decisions that you are making now are coming from a good place that I understand. And the same way that you make those decisions now, when the context changes and we’re married, or we’re in an old age home, or we’re going through some struggle that marks the rest of your life because life is difficult, you’re going to make the same good decisions, because you have healthy and good religious intuition. I’ve been too wordy, I’m sorry.

Zahava Moskowitz:
I kind of want to push back on this point, but also there’s a lasting question I want you to talk about.

David Bashevkin:
Oh, we can debate this out all day.

Zahava Moskowitz:

David Bashevkin:
We’ll have a separate podcast where we talk about growth-oriented versus religious intuition.

Zahava Moskowitz:
For just that. Yeah. There’s a lot. Yeah, there’s a lot to say there and to flesh out, but I appreciate that perspective.

David Bashevkin:
The last part of the interview, I don’t know if it was the most important or the least important, because it was the most relevant specifically for dating, and one of the things she asked me is about, what advice do you have for people who are actually dating right now? And believe it or not, as anyone would hate from somebody who is now married, I do have some measure of advice. And I do speak to a lot of people on this issue, and some of that advice and ideas we’ll talk about both in the outro to this episode as well as in future episodes.
But really, I want to share one thing before you listen to this part because I don’t really delve into it, and that is the notion of checklists of what you insist upon when you date. I personally have a very basic checklist. I envision, to go along with this airplane analogy like the Bermuda Triangle, I envision relationships like getting a plane down the runway, where the relationship itself is when it’s in the air. That’s what it’s all about, but you got to get it into the air.
And I always say there are three things that you need to get that airplane in the air. It’s a very short checklist. Number one is you need to be attracted to your spouse. You don’t need to think that your spouse necessarily is the most beautiful person in the world, though that is a lovely thing to say and even more lovely to feel. That’s fine.
I compare it in some ways to thinking that the gadol hador, the leading rabbi, do you have to believe that he’s the smartest person in the world? No. You have to think that he’s smart. You can’t think that they are foolish or dumb, God forbid, but you don’t need to think that they have the highest IQ in the entire world in order to take their guidance, in order to have them as a leader.
In a similar sense, you don’t need to necessarily think that your spouse is the most beautiful person in the world. And of course, an obvious exception, in case my wife is listening, she happens to be coincidentally been voted, she’s been the People Magazine most beautiful person in the world, I think, 10 years running at least. So I am the exception to this. But I think generally you need to be attracted. You need to be sexually attracted to your spouse. That is number one.

Number two, once you have attraction, and this is very… Now, I’m going to phrase this very importantly, but I always phrase it the same way. You can have no irreconcilable religious differences, no irreconcilable religious differences. What is an irreconcilable religious difference? That changes from person to person. For some people that might just be keeping kosher and Shabbos. For other people that may be wearing a hat and jacket. For other people that may be covering your hair or wearing skirts or whatever it is.
You need to figure out, what are my irreconcilable religious differences? What are the things that I will not be able to make a commitment to somebody with these religious differences? And I urge people to be as minimalist as possible. I actually have a negative theology on this. Don’t think… And this is deliberately in contrast to someone who has the same hashkafa as you. As you will hear over and over again, I absolutely hate the word hashkafa. I think the word itself was invented probably, I don’t know, early ’80s? I would love for somebody to do a real deep dive etymologically of when the word hashkafa became en vogue. It means like your outlook on life.
I don’t believe that you need to have somebody with the same hashkafa as you. I know so many healthy marriages where you have different hashkafas of one degree or another. You need to ensure that you don’t have any irreconcilable religious differences. You can’t have somebody who wants to keep kosher and serve not kosher there. You can’t have somebody who insists on a certain religious commitment and their spouse is undermining that.
That is how I phrased it. I think hashkafa becomes too nebulous, and most people do not spend the remainder of their marriage debating hashkafa. You think about the culture of your home, you think about the religiosity of your home in broader senses, but that emerges after the commitment.
And I don’t like a long checklist of, I don’t know, irreconcilable religious differences because, honestly, our religious lives change and you just want to make sure that there are very clear red lines that you are signing up for. And different people have different red lines, and it’s okay to have more either expansive or very restrictive red lines. You have to figure out what works for you.

And finally, the last part is being able to spend long unstructured time together. I think dating in a way is not a great way to figure out whether you could live with a person. And living with a person sometimes is not the right way to figure out if you can live with a person. So a lot of problems obviously start with that. Aside from halachic issues, which we’re not even going to get into, of course.
But I like being able to spend long unstructured time together. I had a family member who actually did something quite brilliant. They took a long drive together to a common destination. I think they were both going to the same wedding for Shabbos or same aufruf or something like that, and they took a four or five-hour drive together to get to some place for Shabbos. I think that’s a great way to figure out, can we spend unstructured time together, where we are kind of looking at our phones, we’re making phone calls, we’re going to pit stops, we’re picking up food, drinks, or whatever it is, long unstructured amounts of time together? We enjoy being in each other’s company when it’s not an activity, when it’s not a Build-A-Bear or paint night or whatever it is, long unstructured periods of time.
This doesn’t mean 36 hours together. I am not saying that. I’m saying like a long drive, where, I don’t know, you’re going to an out of town wedding together. And you’re driving, I don’t know, three hours to Baltimore, and you’re driving back, and you’re spending time at the wedding, but it’s not structured, it’s not programmed.
That is always my checklist that I advise people. You have to be attracted to one another, there could be no irreconcilable religious differences, and being able to spend long unstructured periods of time together. And really, what happens afterwards, ultimately, is the relationship itself emerges from the commitment itself. And that’s the final part of my conversation about my own dating story with Zahava Moskowitz.

Zahava Moskowitz:
I want to just wrap up, because I overheard you saying this on another person’s podcast. I’ll give a shoutoutto the YUConnects CandiDate podcast, where you had mentioned with Rabbi Ismach that you have an interesting philosophy on dating of why people remain single.

David Bashevkin:
I’ll go through each of them. Number one, the ante gets raised. I felt this. The longer I dated, the more I would hear whispers or say to myself, “I can’t wait to see who you end up with. Oh, my God, this must be somebody so special.” And you feel that the person who you end up with needs to justify the entire trajectory of your personal narrative, and that is not a fair burden to place on anyone else.
The longer you date does not mean the more wow of a person you need to finally commit to, who justifies everything that you do. The longer you date is the more you need to refine and mature what it means to commit to somebody, and what it means to be in love, and what the barriers and expectations need to be to be in love. And I think therapy helps a lot with that. Shout out to therapy.
Your expectations should stay as much as humanly possible, the same, like a flat line, even as the length of your dating goes longer and longer. It doesn’t mean that what you expect can’t evolve, but the level and the wow and what the feeling of being in love should feel like, that should stay the same. And you need to do teshuva to make sure that it’s at the right level. That’s number one.
Number two, take a look at your checklist and make sure that it only has the bare essentials. Because checklists are important, values are important, and sharing values are important, but you need to make sure that no extraneous values sneak in there. Somebody who people thought was cool when they went to camp, somebody who only dresses a certain way, somebody who is a name. I hate that term forever. Nobody knows him. Who cares? I think we creep things up. And when I say checklist, I don’t mean literally on your checklist, but that emotional checklist that we can’t move past unless we feel that they’ve been satisfied. I think we hold on to too much.
And then finally, I’ll say one thing about commitment. I think that the struggle for commitment, and I think I struggle with both of these. I think we talk a lot about our ability to commit and say yes, but I think when people are dating, there is commitment issues with being able to say no. And knowing the difference when you’re in a relationship, afraid to say no, not just to-

Zahava Moskowitz:
You mean to a date or once you’re dating someone or both?

David Bashevkin:
Both, and I’ll add to that list. We’re committed and we’re not able to say no to past conceptions of ourself. We’re committed and we’re afraid to say no to the sense of confidence we have of being beside somebody that isn’t maybe what some people in our lives expected. We are hanging on to too much, and we have commitment issues that we’re afraid to say no to those things holding us back and being able to take a step forward. We’re afraid to say no to aspects of ourselves and say, “You’re not coming along for this part of the journey. We’re changing course. We’re doing something differently.”

Zahava Moskowitz:
Can I ask you for an example? Just because I’m having a harder time, I think, understanding that last one. What would that look like?

David Bashevkin:
Well, commitment in saying no on the most basic sense is you’re in a long relationship that’s going nowhere, and you’re afraid to say no and end this.

Zahava Moskowitz:

David Bashevkin:
But the analogy that I was building on this in the commitment to say no is that you’re in a long relationship not with another person, but with a certain practice or a certain thing that you’ve been holding onto that you have not allowed yourself to move past. Maybe it’s a religious commitment. Maybe it’s going out with a certain guy from, I don’t know, or a girl, from a certain community or a certain profession. You have commitment issues because you’re not willing to say no. You’re not willing to say no one way or the other.
I notice. A family member had this, she grew up in a certain home and she was going out with guys going into chinuch. And I told her, “Why? I don’t think that you have the capacity to do this. And you keep on saying ‘yes’ to these people and going out with them. You have commitment issues because you’re not able to say ‘no’.”
I don’t want to give more detailed examples because their day… I’m afraid to even give one, the one I did, I’m afraid …

Zahava Moskowitz:
Right. Right, right, right. You don’t want to hit on something personal.

David Bashevkin:
This is about finding and constructing your sense of self, and what worked for your friends does not necessarily work for you. And the real work is discovering who you are and building that sense of self of what really works for you.

Zahava Moskowitz:
Right. Or what doesn’t work and that you need to say no to, right?

David Bashevkin:
Correct. Exactly.

Zahava Moskowitz:
No thank you.

David Bashevkin:
Yeah. The one thing that I didn’t really discuss with Zahava, but I think stands at the center of everything that the dating experience has done to shape me, and that is my relationship with commitment itself, what commitment is. And I want to say quite plainly that I was able to develop a healthy relationship with commitment, with relationships, by going to therapy.
For me, and I think for many who are grappling, whether they are in committed relationships or searching for a committed relationship, I found therapy extraordinarily, extraordinarily helpful. And to this very day when I have a child, in the delivery room, after I text my immediate family, I still send a text to the therapist, who I really attribute so much of my ability to be in the relationship and to build the life that I have now to that therapist.
And I reached out to her and asked her to join 18Forty for an interview. She said, no for 1,000 reasons, but I begged and pleaded. I said, “Do me a favor. I just want your basic philosophy of love, commitment, relationships. Let me share it with our audience.” And my therapist, who I no longer see but I’m somewhat in touch with, she’s absolutely amazing. Her name is Dr. Sara Barris. And she shared with me a brief voice note that I really think encapsulates so much of her approach to dating and commitment that, to me, allowed me to cross over the finish line.
I remember being in her office. And I would go to her office and we would have, I think, weekly meetings. And she was so helpful. And I was really stuck at a point. I remember there was one meeting where I think I just cried through one therapy session with that feeling that I began with, that I just want to bring my parents nachas. I want bring joy to those around me. I don’t want to be an issue that needs to be resolved, I want to have the capacity to show gratitude and share gratitude with others.
And finally, I was at an impasse in my dating life, and I was describing the woman who I am married to now, and I was just not sure of what the next move. And I basically just described her and the way that we interact. And she looked at me and she says, “Dovid, she sounds wonderful.” And it was that reaction and her kind of leading me towards what commitment can be, and the confidence to have that commitment, and the knowledge of how painful that commitment was, is what I think allowed me to take that next step.
So I want to share with you a very brief voice note that my therapist, who really helped me conclude or find that reconciliation in my own dating story, this is a message from Dr. Sara Barris.

Sara Barris:
Hi. This is Sara Barris talking about love and marriage. Love is not a commodity, a magic charm that makes us feel good, an emotional fix. Barry Schwartz, expert on the paradox of choice, highlights our consumer culture and that the abundance of options and multitude of alternatives lead to an illusion that there is perfection out there rather than building and deepening a connection through one’s lifetime.
This illusion leads to constant self-appraisal, rumination, “Am I happy? Am I in love? How do I know that I’m feeling it? I look at the couples out there and they all seem happier than we are.” Waiting for the one right person theory, Schwartz observes that, quote, “People walk starry-eyed, looking not into the eyes of their romantic partner, but over their romantic partner’s shoulder in case there might be somebody better walking by.”
In this context, we are uncomfortable without 100% certainty, not willing to take responsibility for our own emotional wellbeing, thinking that love will give me what I need. On the other hand, commitment leads to cultivating versus finding. It leads to effort, investment, and resilience. Commitment helps us raise the threshold of staying in a relationship.

We yearn for perfection in the context of being perfectly imperfect human beings. To be human is to be held together by scars and radiance. Real relationship takes audacity to dig deep into our own vulnerabilities, which can feel daunting. But if we don’t take the exquisite risk, we live with the challenge of not feeling authentic, and we’ll have a hard time seeing ourselves with clarity. Real relationships involve some risky generosity to be able to celebrate the greatness and to give the other person space and permission to be human.
Commitment enables us to affirm resilience in our love, to affirm that thousands of slights that everyday life can make us prone to have not reduced our capacity to deeply appreciate each other. We need to constantly renew our commitment to help jumpstart the potential of the relationship, to make space for ourselves and our partner, to keep our heart and mind open.
And yet, it is important to not whitewash serious issues, especially if one’s own deep values, feelings of self-worth and agency are diminished. We can’t take a shortcut or a spiritual bypass of sorts, where we prematurely transcend our human needs leaving personal values and serious issues by the wayside. Self-awareness and humility helps us to seek guidance from rabbanim and skillful professionals.

And so love begins where the movie ends. Building and deepening the connection is work that begins before marriage and continues for our lifetime. The ideals in relationship also develop over time. They evolve to incorporate new needs and changing challenges. So love is an ability to cultivate not just a feeling. Love is an action that involves care, commitment, responsibility, respect, trust, and playfulness, yes, playfulness, deep mercy, and light touch.
And so happily ever after is a privilege and a blessing that comes with hard work, lifelong intentionality, and commitment. It is the holiest work, and the ongoing grace that comes along with it is a boundless gift.

David Bashevkin:
This distinction between consumer culture and maybe what I would call commitment culture is everything that stays with me to this day, the difficulty of moving away from being a consumer. Consumers want to mitigate risk. They want to go through the checklist and avoid any heartbreak or any pain. When you go to buy a car, you check reviews, you check product recommendations, you look for a warranty. You don’t want to get stuck in it. You’re really searching for perfection. You’re searching for something that’s going to align perfectly, as opposed to commitment in romantic relationships, where I believe the relationship doesn’t even exist until the commitment is made. And what really dating is all about is finding the circumstances and context to make that commitment.
It reminds me of an interview that I heard, I think it was with Aziz Ansari and Howard Stern, I couldn’t find it online, though I certainly looked for it, where Howard Stern asked Aziz Ansari about his parents’ marriage. His parents are from India and were set up in an arranged marriage. And he said, “What is their married life like? How did that lead to anything?” And he said, “It’s actually very strong because what allowed them to have a strong marriage is that they realized that you don’t make a commitment after the pot is boiling, but,” so to speak, “it is only following a commitment that you actually have a relationship to nurture and create.”
And very often, we wait for everything to be perfect in order to first make that commitment, when ultimately, in a certain sense, the relationship doesn’t exist until there is a commitment. The mystery of two people coming together and being committed to one another, whether romantically or even in a friendship or even in religious life, it doesn’t really exist until that commitment is there, until that strength of the commitment is there.
It’s why I wrote in an essay why Jewish marriage is really symbolized by the kesubah. The way that we symbolize our marriages, you see in so many homes hung on the walls, is the kesubah document. The kesubah document is really mundane. It is very kind of boring and pedestrian, but I think it’s come to represent the Jewish notion of marriage because the kesubah is about commitment and the ordinariness of commitment, because it’s only through commitment that a relationship ultimately emerges.
And that’s part of the scariness, and part of what I was dealing with when I was dating. I would have recurring dreams of being at my own wedding and not knowing who the bride was, and not knowing when this happened or when this was planned, and kind of feeling alienated in my own self. And what Dr. Barris allowed me to realize and embrace is the mystery of commitment, the joy of commitment, and how fostering your sense of self and your relationship with others only comes through that lifelong commitment. Which may seem more volatile, it may seem less stable, because things do change over the course of your life. But it is only through commitment that I have learned through my own dating story that I have learned that it’s not about finding that perfection and committing to it, but it is through the act of commitment that we’re able to build those perfectly imperfect lives.

So thank you so much for listening. This episode, as I mentioned, was sponsored by my dearest friends Jerry and Esther Williams in honor of the work of 18Forty, but more importantly, in honor of the incredible work and all those who support the work of Shalom Task Force.
And once again, I want to remind all of our listeners, there is a Shalom Task Force dinner this coming Sunday. That is December 11th. You can check out Shalom Task Force’s website at I know Jerry and Esther for a very, very long time. I always call Esther my honorary mother-in-law, and I am so grateful for their support and encouragement of the work that we do.

This episode, like so many episodes, was edited by our dearest friend Denah Emerson. And it wouldn’t be a Jewish podcast without a little bit of Jewish guilt. If you enjoyed this episode or any episode, please subscribe, rate, and review. Tell your friends about it. You could also donate at It really helps us reach new listeners and continue putting out great content.

You could also leave us a voicemail with feedback or questions that we may play on a future episode. That number is 917-720-5629. I want to encourage our listeners, particularly on this topic, people who are still in this world of dating romantically, we really want to hear from you. We are looking for firsthand people talking about their experiences. I plead. You don’t have to share your name. I think there’s so much to learn from that experience. Please leave us a voicemail. Once again, that’s 917-720-5629.

If you’d like to learn more about this topic or some of the other great ones we’ve covered in the past, be sure to check out That’s the number one, eight, followed by the word forty, F-O-R-T-Y, dot org. You can also find videos, articles, and recommended readin. Thank you so much for listening and stay curious, my friends