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Dating is terrible

There, I said it.

Go ahead, call me a complainer. I freely admit it: I am a complainer. I do not force myself to "only see the positive" or "look on the bright side of life" (always or ever, really). When something bothers me, I have a very hard time not vocalizing that. And a lot of things bother me!

Sometimes, you just have to tell it like it is. Today is one of those days. After nearly a year of blogging silence, I came here to say that dating is terrible. Even when it's going great, it's pretty terrible.

Dating is terrible because (in no particular order and this list is by no means exhaustive):

  • Does he like me?  
    • How does he like me?
    • Does he just want to be buddies with me or is he attracted to me?
      (I don't need more buddies. Thank God, I have many friends whom I adore who also seem to like me.)

  • If he's shy, is he:
    • shy, but attracted to me?
    • shy, but not attracted to me?

  • Is he awkward because he likes me?
    Is he awkward and doesn't like me, but is too awkward to say so?

  • Am I attracted to him?

  • Why does he pick his nose in public?
    • Is that reason enough to not go on a second date with someone?
    • Is rejecting someone for picking his nose in public being "too picky"? Too shallow?
    • Would any woman who picked her nose in public get a second date, ever?

  • How am I going to navigate my own anxiety around this thing with this other person? Ugh! It's easier just to be alone! I should have left well enough alone and not dipped a toe back into dating. Dating is terrible.

  • Oh, wait, I think he likes me! It's hard to tell, but he does seem to like me.
    • First: Swoon.
    • Next: Do I like him?
    • I should really give him a chance. People don't come along who like me every day, you know!
    • I think I kind of like him. Is that enough?
      • I enjoyed spending time with him at least once.
      • I wouldn't run away if I saw him heading towards me at kiddush. (Back when there was kiddush. Back when I went to shul. In the Before Times.)
      • Could this become something more?
      • Will I grow to like him more over time if the first date was great, the second date was "eh" and the third date wasn't fun at all? No, right? Things are heading in the wrong direction.
    • Do I not like him more because I am being too picky?

  • I like him! He seems to like me, too! YAY! 
    • What if he's incapable of being in a relationship and bails just as things get emotionally interesting?
    • What if he's incapable of being in a relationship and bails before things get emotionally interesting?

  • We spoke on the phone and apparently have nothing in common. Should we go on a first date anyway?

  • We went on a first date and it's really hard to have a conversation with him! No natural "back and forth" happens.
    • He asks me a list of questions, like, "What is your favorite movie?" "What is your favorite book?" "What kind of music do you like?" but I find those questions rather boring, maybe mostly because I don't really keep a list of my favorites handy. I enjoy lots of movies and books and a wide variety of music, but don't have favorites, per se. Despite having asked me all of these questions on our first date, he repeats some of them on our second date. Am I supposed to ask him these things, too, even though I'm not really that interested in his  answers?
    • What I want to know about a person I'm on a date with is:
      • How does he see the world?
      • How does he relate to the people around him?
      • What is important to him in life?
      • What does he think of:
        • kindness?
        • education?
        • poverty?
        • sexism?
        • racism?
        • classism?
        • behavioral economics?
        • grammar?
        • intelligence?
        • children?
So if I am going to ask him questions, they'll be questions that might elicit answers that would shed light on some of those things. I don't really care what his favorite book, movie, or music are. Does that make me a terrible person?
    • Can a person learn to become a better conversationalist in their 30s, 40s, or 50s?
    • Does it matter if the person is a good conversationalist or not?
    • Is most of life about conversations or about stuff like taking out the garbage, washing the floor, doing laundry, making sure we don't run out of toilet paper, and meal planning and prep?

  • I asked him questions about himself, but he hasn't asked me any questions about myself. Is he uninterested in me or just doesn't know to ask questions about the person you're on a date with? How can a person in their 30s, 40s, or 50s not know that?

  • What's a deal-breaker? What isn't?
    • Do I have too many?
    • No, I probably have too few. "Not being able to hold a conversation" and "picks his nose in public" should definitely be deal-breakers.

  • Why does he only want to be in touch on weekends?
    • What's going on in his head/heart/mind from Monday-Friday? I can't know, because he doesn't tell me.
    • Is that he when dates other women?
    • Is that when he freaks out about being in a relationship and plots the gentlest way to end things with me?

  • He's in his 30s and he wants five children but has never taken care of a child in his life. No, not even two hours of babysitting for a niece or nephew. All of his interactions with children have been brief and at the Shabbat meals of friends.
    • Should I illuminate for him how much work children are and how he might want to reconsider his plan to have five children?
    • Or should I let him stay in the dark for now and pretend that I, too, want to birth and raise five children?
    • Is that deceitful?
    • Is no man ever going to want to have children if he realizes how much work they are? Probably, yes. That sounds about right.
    • For the future of the species, should women not let men know how much work children are and how utterly thankless so much of that work is?

  • He isn't sure that he wants children at all. He might be okay with one or two.
    • Do men who feel like they might be okay with one or two children, but would happily live the rest of their lives without children, make good fathers if/when they end up having children?
    • Do I care? What if he's a terrible father but a good spouse? Is that good enough?
    • Can anyone actually know how a person will end up parenting before they have children of their own?

  • Wait, do I still want a child or children? I'm getting old, man, and the idea of going without sleep for years in a row and worrying more, constantly, about other people for the next few decades (or possibly forever) sounds less doable than it did when I was in my 20s. Especially if the person I'm doing it with is even older than I am and has never really thought about whether he wants children or not. And isn't inclined to do the hard work/heavy labor of child rearing.

  • If I mention children too early on, he'll freak out.

  • If I mention monogamy too early on, he'll freak out.

  • If I ask him how things are going too early on, he'll freak out.

  • What would make me freak out?
    • I guess if he said, "I love you" on the 2nd or 3rd date, I might freak out a bit.
    • Short of that...nothing?
    • I mean, if he brought his parents along on a date without discussing it with me first, that would freak me out. And be weird.

  • How weird is too weird, anyway?
    • Say he tells me that he has a foot fetish in our second phone call, when we haven't yet been on a date? Too weird?
      • Maybe a foot fetish itself isn't too weird, but telling someone you have a foot fetish during your second conversation is too weird.
    • What if he commits a few social faux pas? Adorable and endearing or, good Lord, no, too much?
    • What if he likes to go on and on about things that don't interest you at all and never checks in to see if it's interesting for you?
    • Oh, God, what if I do that?

  • Why aren't men who know that they aren't relationship-ready doing the things that would make them relationship-ready? Therapy, support groups, talking to friends about dating and emotional intimacy?

  • God, I really wish all men who were dating women made sure that they had friends--male, female, non-binary--to talk to about dating and relationships. Men, please try to develop these relationships if you don't already have them. Parents of sons, please try to encourage your sons to develop these kinds of relationships with their peers, mentors, whomever. (They can talk to you about dating, too, but they should also have other people to talk to about these things!) Thank you, on behalf of women everywhere!

  • Hello. I'm thinking about him. Is he thinking about me? Or has he not given my existence the merest hint of thought or attention since we last spoke on the phone or saw each other?

It's been 20+ years of this! 20+ years, man! That's a long time to be dealing with this stuff. For at least 15 of those years, I'd have much rather been dealing with navigating partnered life, childbirth and rearing, and the rest of life. Not this merry-go-round of dating.

I mean, I do get off the merry-go-round for a bit, each time a relationship or attempt-at-a-relationship crumbles into dust. I take a break. I focus on other things. Anything but dating! Seeing friends. Doing fun-for-me things alone in New York City. Reveling, just a little, in not having to truly consider anyone else's deepest, most vulnerable feelings for days--sometimes weeks!--in a row.

So it hasn't been 20 years of doing this nonstop.

But, also, if we're being honest, it started more than 20 years ago, with the first male-friend-with-whom-I-fell-in-love back in...whenever that was. (This never worked out for me. Ever. Male friends on whom I had crushes never wanted to be more than friends with me. Men get all bitter when this happens and call it being "friend-zoned" and claim that no women want to date them, ever. I don't find that to be the case. Just that men with whom I am friends first don't end up wanting to date me. Men whom I first meet/get to know in a dating context sometimes want to date me.)

The only thing that makes me keep going back to it (between breaks to forget about the whole enterprise) is the slimmest, slightest possibility that I'll find someone:

  • Whom I definitely like.

  • Who likes me. That is, his innards liquefy when he sees or thinks about me, just as mine liquefy when I see or think about him.

  • Who is weird in all the right kinds of ways!
    • Whose slip-ups are humanizing and endearing, not cringe-worthy.
    • Whose slight awkwardness makes me feel more comfortable with my own slight awkwardness, not like I want to sink into the ground on the spot.

  • Whom is fun to get to know. Plumbing the depths of his mind and soul is so...nice! We feel so compatible. Seeing him is 95% pleasant and only 5% stressful anxiety wondering about how he feels about me, which is a pretty good ratio! (If there wasn't that 5% frisson of anxiety, I probably don't like him enough to keep seeing him.)

  • Who is either currently capable of being in a committed, monogamous relationship of some kind
    Who is not, but is willing to, starting today, put in the work of becoming capable of such.

And then, after that continues to go well for some time, I could potentially end up with:

  • A life partner.

  • A person who has my back.

  • A person who is in my corner.

  • Insert further relevant metaphors here.

  • A person I can talk to regularly about my day-to-day life. (He doesn't think I talk too much.)

  • A person who is interested in what's going on with me, emotionally, intellectually, relationally, professionally, socially, etc.

  • A person who will talk to me about their day-to-day life.

  • A person whose experience I am interested in. I want to know what's going on with him emotionally, intellectually, relationally, professionally, socially, etc. I don't think he talks too much (most of the time).

  • A thoroughly kind person who would never intentionally hurt me and who, after unintentionally hurting me, is interested in discussion, repair, mitigation.

  • Someone who thinks being kind is more important than being smart.

  • Someone who wants to be the change that they hope to see in the world.

  • Someone to be with in companionable silence.

  • Someone who doesn't think I'm too much.

  • Someone whom I don't think is too much.

  • Someone who disagrees with me respectfully.

  • Someone with whom I disagree respectfully.

  • Someone whom I love even when life is hard.

  • Someone who loves me even when life is hard.

Sometimes, I think that maybe my issue is not that I am "too picky," but that I just want too much. I want more than any person can be for or to me. Is that the issue with me and dating?

Or am I just too anxious to be able to handle dating? I don't know. Maybe. I obviously know that I'm anxious, but I mostly think that I worry the right amount about things, like never being partnered and winding up sick and alone when I'm 71. As bad as being single at 21, 31, and 41 were/are, I think being single at 71 would be worse. (Maybe I'm wrong about that. I don't think being 71 itself would be worse, just the being-single part of it.)


Or maybe that person is out there, but he doesn't happen to be Jewish. How much of my Jewish life or practice would I be willing to jettison in exchange for those things that I have wanted, so badly, for over two decades? I think about this not-infrequently. 

Two things that have kept me from doing this are:

  • What if I jettisoned a lot of my Jewish practice and still ended up alone? That's a lose-lose scenario to me.
  • What if I jettisoned a lot of my Jewish practice and ended up paired, but deeply regret jettisoning my Jewish practice? That's something that's difficult to backtrack from, I imagine, once one is paired.

Don't get me wrong--over the years, since I was 20 or so, I have ever-so-slowly slip-slided away from the strictly Orthodox practices of my youth.

עָוִיתִי, פָּשַעְתִּי, and חָטָאתִי are definitely words that apply to my life.

I was a very frum 18-year-old and then, just like they promised me in yeshiva, I went to secular college and, due to a number of factors, gradually became less frum.


I have made various attempts to shore up some of my Jewish practices in the years since. I sometimes miss the person I was at 18. So earnest! So non-hypocritical! So straight-and-narrow! Others, I have simply let fall away. Sometimes, I am briefly so frum (as in, I daven mincha on a weekday--at this point, it's been years, I think) and I deeply, in my kishkas, miss being so frum all the time.

But, also, despite the glacially slow slip-sliding that I have done since I was 20 or so, I still live a very, very Jewish life. And I dream of living that very Jewish life with someone else who also wants to live a very Jewish life, even if he is fuzzy on some of the details or doesn't fully practice observant, halakhic Jewish tradition.

Despite over two decades of slip-sliding, I still pretty much do, and don't do, the same things as when I was 20-ish. (I can't think of slip-sliding without thinking of שׁ֚וּבוּ בָּנִ֣ים שׁוֹבָבִ֔ים אֶרְפָּ֖ה מְשׁוּבֹתֵיכֶ֑ם. That's how Jewish I still am.) I do go to shul less often these days; that's true.

That slip-sliding never became a wholesale jettisoning, as would likely be required to be in a serious relationship with someone who wasn't Jewish and also not interested in personally engaging in Jewish practice. (I think that some people who aren't Jewish are interested in personally engaging in Jewish practice, and if I found a person like that, less wholesale jettisoning might be necessary.)

Part of what angers me about the conversation around intermarriage is that not enough Jewish men (and some women) consider that, for many Jewish women, the choices are, quite literally, lifelong singlehood or intermarriage. There simply aren't enough Jewish men out there who want to be in relationships and are willing to do the self-work necessary to be in relationships, for all of the Jewish women who want to be in relationships and are willing to do the self-work necessary to be in relationships.

(This is true for a number of demographic and sociological reasons, including:

  • more Jewish men who, especially in their 20s and 30s, partner with non-Jewish women than women who do the same;
  • more Jewish By Choice women than men;
  • more men than women have Autism Spectrum Disorder and other neurological differences that make it hard for neurotypical women to become their partners; 
  • more men than women who, for whatever reason(s), don't decide to get serious about seeking a life partner until they're in their 50s and are then only willing to date women who are 37 or younger because they want to have biological children with someone who will be their biological children's biological mother;
  • and other things I'm not thinking of now.

But it's true. I'm sure of it and have been for over a decade. It's not because women are "too focused on their careers" or "uninterested in marriage." I promise you, it's not.)

Would you truly tell all of the never-married Jewish women in their 40s, 50s, 60s, and beyond that they must stay single forever rather than date and possibly marry non-Jewish men? That seems cruel.

"But, Abacaxi Mamao, what can I do about this?" 


I hear you all the way from here. First of all, thank you for caring!

Second of all, here are some things that you can do. If not for me, then for future generations of single Jewish women.

  1. You can ask your single Jewish female friends if they want to be set up and with whom. Then, for those (and only those) who express interest in being set up, you can set up your single Jewish female friends with single Jewish men or, for Jewish women who are open to this, with non-Jewish men who are interested in living vibrant Jewish lives. (They don't need to, in your opinion, be perfectly aligned with one another to be set up. The perfect is the enemy of the good here. But if you're setting people up totally randomly, at least let them know that so they know what they're walking into: "You're both greying, so I thought I'd set you up." "You're both smart, so I thought I'd set you up." "You both live in [same large city], so I thought I'd set you up.")

  2. You can foster close relationships with the single Jewish men who are already in your life, such that they have someone to talk to about dating and relationships, thus helping pull them back from the brink of panic when they get close to a woman in a dating relationship.
    • "Wait, so I should try to be their therapist?"
    • No. Please don't try to therapize your friends. What your male friends need is your friendship. You should be their friend!
    • Also, encourage everyone you know who seems interested in deep, abiding change in their life to get regular counseling or therapy with a qualified therapist. (Not a life coach. A therapist.)

  3. Are you a parent of a son or sons? By living a rich, vibrant, communal, and connected Jewish life yourself, you can raise Jewish boys to become men who will want to be in relationships with Jewish women. Will it work 100% of the time? No. It won't. (Daughters also benefit from this!)

  4. Are you a parent of a son or sons? By talking with him/them about their inner life and feelings, you will help them become a person who can do so outside of your own family, with friends and partners alike. And this can only be good for humanity. By modeling empathy, validation, and connection with them, you help them grow up to be empathic, validating of, and connected with others. (Daughters also benefit from this!)

  5. Are you a parent of a son or sons? Do they struggle to identify their feelings? That's okay. It can be hard to identify feelings, but it's a skill that can be practiced and learned. Adults can learn to do it. Children can learn to do it. (Therapy helps.) Some people who have trouble discussing their feelings have an easier time writing about their feelings, acting out their feelings in play, or exploring their feelings through other modalities (art, music, sports). The important thing, I think, is to get in the habit of identifying and exploring one's feelings. That's a prerequisite for ever being able to communicate them with someone else. (Daughters also benefit from this. But girls are socialized to identify and verbalize their feelings more than boys are.)

  6. Are you a parent of a son or sons? Are they struggling socially or interpersonally? Teach them and model for them that therapy is a wonderful thing and encourage them to engage in it. If the first therapist is a bad fit, seek one who is a better fit. (Daughters also benefit from this!)

Thank you for reading my brain dump on dating today.

And good luck to us all!

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