Bullish Life: 3 Romantic Mistakes That Young Women Make That Cause Weeping Among The Angels And Kittens

Jennifer Dziura writes life coaching advice every Tuesday here on TheGloss, and career coaching advice Fridays on TheGrindstone.

Last week on TheGrindstone, we talked about missteps in the professional world in Bullish: 3 Career Mistakes Young Women Make (And How To Smash The Competition).

This week on TheGloss, let’s talk about romantic mistakes that can wreck your twenties and completely derail other aspects of your life (it’s hard to work on your career when kittens weep for your pain!)

Mistake #1: Assuming that just because a man is older, he’s more mature.

I have more than once made the mistake of assuming that just because a man is over a certain age, he’s necessary possessed of oh-so-much gravitas. I mean, if I were a man, I’d make damn sure that I knew how to order scotch before the time that my chest hair started going gray.

(My BFF has often been the subject of vicious put-downs from men who claim that she’s “only” successful in her career because she has big tits. As though that were even possible. Her response: “Male attractiveness is really easy. Go to the gym and get a nice suit. Shut the fuck up, I’m working.”)

As I said in Bullish: How to Age with Panache and Strategic Awesomeness, aging is a parade of indignities — to compensate, you must gather more, well … dignities. But my opinion is by no means universal.

So I have been quite surprised when men over forty refer to their shoes as “kicks,” decorate with posters, think it’s cool to live with roommates, cannot tell a hand towel from a dish towel, and laugh at the thought that they could be responsible for the care of a small child.

My dad, a Navy man, has always liked to say, “When you assume, you make an ASS out of U and ME.”

Mistake #2: Assuming that two people mean the same thing by “love.”

A reader I’ll call Betsy Ross wrote in to say:

I know you don’t normally deal with Man Issues, but I really like your advice and need to be more of a badass, so you seem like the one to talk to. I started dating a guy three years ago when I was 31 and he was 39. We both said on our 2nd date that we wanted kids. So I thought he understood that we would have to have them soon because.. that’s how biology works? We made references all the time, like hinting that we could name our kid something hilarious based on a movie we both liked, et cetera. After three years when I said we should really get on it and have a baby he said that he loved me but didn’t know when he would EVER be ready to have kids. I said, um, you know, I think you kind of just killed my last life chance to have biological children, since I’ve been with you for ages 31-34 – really, you never did the math? He looked at me like I was crazy. How is that crazy?

What a heartbreaking situation, Betsy. And almost a taboo one to talk about, so I’m glad you wrote in.

I could find plenty of conservative authors who would say that the sexual revolution backfired on women — see Dr. Miriam Grossman’s Unprotected, for one. And then it would only be fair to hit back with Jessica Valenti’s The Purity Myth: How America’s Obsession with Virginity Is Hurting Young Women.

That debate is a bit above my pay grade — I’m here to help us direct our lives to where we want to be, regardless of the situation around us. As I see it, the situation around us is simply one in which nothing can be assumed.

I recently went on a first date with a man who was bragging about how non-judgmental he was. Interesting, I thought. That is actually not a good way to impress me. I believe in making good judgments. I believe in judging racists, drunk drivers, and people who act unethically in a variety of other ways. FirstDateGuy followed up his comments with, “I wouldn’t judge a guy who got divorced because he was unhappy.”

“Well,” I said, “what if his wife is very unhappy that he’s divorcing her based on possibly ephemeral feelings, when he would probably have promised in his wedding vows precisely not to do that?”

He was truly baffled. I continued, in my Socratic-method voice, “I’m curious, then. What do you think the point of marriage is, if in your view it can be ended based on the same reasons you would end a dating relationship?”

I’ll end this anecdote here (strangely, my debate-style Inquisition did not tank the date, although I declined to see him again); the point I want to make is just that you can’t assume that any two people automatically mean the same thing by “love,” “marriage,” “commitment,” or any other warm-and-fuzzy words.

My first thought to Betsy’s question was, “Wow, that guy doesn’t really love you at all, because he wasn’t really looking out for your best interests.”

Why do I think that, though?

Hrm. Because I grew up in a moderately Christian environment, and some Christians at some point told me that, “Love is a commitment to the best interests of the other person.”

These are the same Christians who think gay people are going to hell, that the earth is 6,000 years old, and that dinosaurs are a trick; I have huge problems with them for many other reasons. But I do think that this idea of love is a good, decent, and humanistic one. (I’m also not saying that Christians invented this. They just passed it to me through cultural osmosis.)

Undoubtedly, Betsy’s boyfriend meant something else. He probably meant that he had intense feelings which he acted upon through practicing monogamy and doing nice things. He probably thought that meant he was doing a pretty good job and being a pretty good person.

He probably didn’t think anything else was required of him. He didn’t think he was supposed to play chess three steps ahead and think about what was best for Betsy. He didn’t think about the fact that there’s an opportunity cost to everything; by staying with him, Betsy was prevented from actually achieving her goal of having children. As I wrote in Bullish Life: Are Your Friends “Supportive” or “Enabling”?, sometimes being nice in the moment isn’t being nice at all.

The only rational response to this is to accept a position of existentialist dating. “Love” does not necessarily mean what you think it means. Every term that might get thrown out in a romantic relationship requires further definition. Someone who loves you is not necessarily saying that he’s got your back. At all.

Lots of men are going to tell you they love you. A lot of them have no idea what they’re talking about.

Mistake #3: Thinking Things Will All Work Out, Because They “Have To”

I was once on a date with a guy who said, “The reason I like you is that you’re the only woman I know who’s logical.”

Oh no, I thought. You are a terrible misogynist who has just insulted more than half of my friends and role models. I think that you are ragingly arrogant and that what you mean is, I like you because you are agreeing with me right now.

I sighed, and said, “Why do you think all other women are illogical?”

“Well, for instance,” he said, “how come every time you sleep with one, she assumes you’re in love with her?”

I sighed. Deeply. “Well, you’re a human being. Are you ever in a situation where you kind of assume the best, because the worst is too horrible to think about?”

“Sure,” he said, not apparently seeing the connection.


“Oh.” The rest of dinner was pretty silent.

The brave new world we live in in which people now spend 10-20 years dating before committing to a life partner (if they ever do) necessarily implies that we will all be passing one another like ships in the night, or getting together and breaking up, repeatedly, for a very long time.

At least in New York, most men blithely expect to spend their twenties devastating women (*Shrug.* It’s not my fault. We weren’t married or anything), and then, in their late thirties or forties, they want to find some special lady who hasn’t been devastated.

It’s not a good system. It’s a prime violation of Kant’s Categorical Imperative, which posits that ethical behavior means acting as though you would will your actions to be a universal law — in other words, don’t do anything that, if everyone did it, would make your own actions and desires completely impracticable.

In this sense, your dating life is very much like your career, in that you will achieve only disaster by thinking that someone else has a grand plan for you. (In fact, one of the very first Bullish columns approached this issue from the opposite angle: Bullish: How Business is Like Dating).

The universe doesn’t have a grand plan for you. Men in general certainly do not have a grand plan for you. Your company doesn’t have a grand plan for your career. No one is watching your back. Your parents probably love you very much, but they’re just watching from the sidelines at this point, and possibly offering up your childhood room rent-free in case you fail. There’s no master plan, no deus ex machina to tie up the loose ends, no poetic justice to make your pain meaningful.

When people write in asking for career advice, I usually reply with a plethora of practical suggestions (see Bullish: How To Make Money From Being Hip As All Fucking Hell). I’m afraid I can’t offer Betsy much more than sympathy, and some guidelines for the future.

Strangely, I’ve quoted my dad’s favorite expression — “When you assume, you make an ASS out of U and ME” — twice this week, both in front of a classroom, teaching logic, and here, encouraging ladies not to let wishful thinking send them down a rabbit hole of unpleasantness. Somewhere, a sad kitten is making rainbows with its tears.

Just as you must design and direct your career (see Bullish: Are You Under-Reinvesting in Your Career?), the same is true of your romantic life. The universe is indifferent. Some bullishness is in order.

Share This Post:
    • sara

      “Lots of men are going to tell you they love you. A lot of them have no idea what they’re talking about.”<– Dear God. That summarizes it.

      "…most men blithely expect to spend their twenties devastating women…and then, in their late thirties or forties, they want to find some special lady who hasn’t been devastated."<–My add would be avoid "most" men and find the type of guy who spent his 20s BEING devastated by women. Seriously…that would have saved me mounds and mounds of time.

    • Baker Girl

      Oh my god!!! Gloss you hit the nail on the head with my life. Relationship with a guy just ended and all of of this applies. I wish I knew now what i didn’t know then!

    • k

      I really resonated with the #3. I made it once and it was enough! Unfortunately, I have a very close friend who hasn’t quite accepted it yet. She’s very religious so sex for her MUST have meaning or else it would end her world. A standard bang-and-bail can turn into a grand love affair (just without the guy around). It’s difficult to comfort someone like that. Someone who won’t let go. Ever. To the point of delusion.

    • Eve

      Ugh, ugh, ugh, the “you’re an exceptional female” thing. WHY does any guy think that is a good compliment? “Most women suck, but YOU don’t.” Oh, maybe because they’ve met enough women with internalized sexism who hate other women and are glad to hear they’re different and special. Thank you for setting him straight, Jen.

      • Nick

        ha yes typifying people by group makes you seem sauve and sophisticated

    • Bob V

      What I’ve noticed about many men is that we can very often just go along with things just to extend happy moments. We want our relationships to go smoothly, so we assume things will move along a desirable course for all involved as long as everyone is smiling.

      Regarding kids, I think women need to keep in mind that they are the holders of the ticking time bomb, so they will unfortunately need to make sure they aren’t stuck with the consequences when it goes off.

      Betsy did a good job of this. She (1) brought it up early in the relationship and (2) talked about names for their (projected) kids. That should have been more than enough if she wasn’t dating someone who’s unusually selfish. I think she was dating such a guy though We often aren’t planning ahead for the women in our lives, but this guy planned along with her and then announced that he didn’t like the plan once he was called upon to actually do something.

      If there is some way to screen for selfish guys, that might have been a way to avoid the situation. Another thing might have been to specifically talk about timing using a serious voice when neither of you is eating or watching TV or doing anything else that could give us an excuse to pay less attention than we should. I wish we initiated more of those conversations, but the task usually fall to the ladies to do.

      • Nick

        Saying half truths to sustain a happy moment or a relationship is hardly a male only issue. All people do this.

      • Bob V

        True. Many people aren’t adults. And their are certainly non-adult women and adult males. The costs of going with the flow fall disproportionately on a woman in her 30s who wants to have kids though. This means that the burden falls on them, which I think was Jen’s point: don’t count on others to plan out your future.

    • Nick

      Betsy in your story mad a tragic mistake. If having kids was important to her, talking about it twice in 3 years is not enough. I know talking about kids inspired anxiety, but its what you think is important.

      • Bob V

        Nick, she wrote:
        “We made references all the time, like hinting that we could name our kid something hilarious based on a movie we both liked, et cetera.”

        I assume “all the time” is an exaggeration, but it’s got to be more than twice.

    • Jennifer Wright

      I’m curious about what the better alternative is here, though. Let’s say I want to have kids. You can certainly make that clear, and it sounds like something Betsy referenced on a pretty regular basis (although there are a ton of dating manuals that say you should never bring it up for fear of sending your boyfriend running).

      Still, I think we’d probably agree that it would be ludicrous to lead into the first date by saying “I want to be preggers in a year. You up for that? You got strong sperm?” Because NO ONE IS UP FOR THAT. Besides, it probably takes at least a year before you could even decide whether you might be willing to have kids with someone. So, no matter what, it’s possible you’re going to spend time you can’t get back with someone who wouldn’t be a fit parent. And by the time you’ve figured that out, all your eggs will be dead.

      I suppose one option would be to say “just be successful enough that you can have kids on your own” but, goodness, being a single parent seems terribly hard. Of course you could get a nanny (have I mentioned you’re going to have to be awfully successful?) but it seems like the desirable situation would be to have someone else as invested in a child’s well being as you are to be able to take care of the kid on a sunday when you wanted to go out and, you know, get a haircut. Or do other grown-up stuff.

      • Nick

        “takes a year”

        Is that really true? I feel like in Austin I know many mid40s women very stressed about wanting to have children. Like NYC, this city has a large perpetually dating class.

        Every bird I see exists despite the fact that they have no job or pay rent. We have these presumptions about what it means to live and love but they often delude us. I know this is terrible advice, but sometimes in life, you should do what you want first, and damn the consequences second. Be bold.

    • Theo

      Are you fucking kidding me? Kant’s categorical imperative is the rule that requires a person to give a stranger who wants to murder their friend directions to where their friend is. It’s not a rule to live by.

      And if you’re judging future husbands by Kant, you’re doing it wrong.

    • Cait

      I feel for Betsy but I think her problem (and also that of your response, Jen, though normally I am 100% behind everything you write) is also that joking about silly baby names is not the same as having an adult conversation with your partner about the future of your family. Why do women set the bar so low for men? Why can’t women expect to be able to have frank, adult conversations about what will likely be THE most important decision of their lives?

      I wonder if by constantly warning other woman not to “send men packing” by discussing important issues early on, we are sending a message to those men who actually want children and are excited to have these conversations that there is something wrong with them. (And yes, I have proof that these men exist – my husband is one of them!)

    • rob o

      Really, using Kant and other half told ideas to justify being angry about someone else not falling in line with your own selfishness. I understand this may not be published because it doesn’t agree with the article but here goes.
      It is no mystery what men want. Never has been. Men want a woman who will not demand huge parts of their life and yet be supportive and loving and willing and receptive in the bedroom (or exit hall in the mall). To say that a man is a misoynistic, because he finds a woman refreshing, and maybe less selfish about what she wants, just seems bad form. Is that the new word for all insults about men. It seems thier is something women are expecting of men, that they most likely will not find, and that is the brain of a woman. I’ve heard tell that Forest Gump, is the ideal man. I supose one could do worse.
      I also know that for some women as soon as they have sex with a man they start expecting the mans world to change to suit them. I have never understrood this. I like the Idea of straight talk about whats happening about what is expected and where we both believe this is going. I also like the idea of not being held hostage by emotional,”But I thought you loved me”. I also like the idea of not being afraid to walk away if it isn’t what your looking for. Why is everyone so afraid to start, and possibly walk away, if it is not right. Everyone I’ve ever met or been involved with has taught me something.
      I also agree with Jenn, If you want children, both parents should be in a position emotional and financial, to walk away and/or take care of the children independantly before the children are even concieved or agreed upon. How is it, that it turns out, to be all mens fault, for not agreeing with what some womans, ideal model, that no one even told them existed.
      When does each gender just take responsibility for they’re own side, and stop worring what the other is doing, and just go out and meet, and be, and learn ,from as many people as possible, until they them selves learn enough about (about them selves) this world and a possible partner to make a commitment and continue to be honest and up front about wants wishes and desires.
      I think love exists! I think it happens all the time. I think it it immature and dishonest at best, most of the time. (Oh I hope he/she likes me. I better not do/say x or i might scare them away). I started doing and saying x, because I have to sleep with me for ever. I think I have found someone who doing and saying what I believe is absolutely fine with and her doing that is fine with me. We disagree, we argue and at the end we love each other we have both learned past immature love, and gotten to, I Love You, who you are and what you stand for, I might not agree sometimes but I still love you.
      I also believe that Kant was all for telling the truth, all the time reguardless of the consequeses, I believe this is known as integrity. telling the thruth, and the whole truth even if it scares them off might be better than finding out later that you both want something so different and now your stuck and again afraid to leave. I hope we can all get along soon. I do not stand for manipulation, just ask me, and accept the fact that the answer might be no. then you make your own decision accordingly, or sell out your soul and live a lie and continue blaming the other gender be it men or women.

    • Jennifer Dziura

      Hello, everyone! Thanks Sara, Baker Girl, k, and Eve! I write these for my ladies, of course :)

      Theo et al. — yes, there are many fine objections to Kant. In fact, I specifically remember being told as a small child by my mother that lying was wrong, unless it was to a strange man who wants to hurt people or wants you to go somewhere with him. (Thanks, mom!) But there are many appropriate “Kantian” situations — for instance, don’t borrow money from a friend if you don’t intend to pay it back, because if everyone did that, no one would lend money in the first place. So, don’t go around hurting people’s feelings willy-nilly if you don’t want to live in a world in which women act as though their feelings are likely to be hurt.

      Cait, you make a fine point, and one that I didn’t mention — Betsy’s joking about baby names is not the same as having a serious adult conversation. But it’s also so taboo for women to talk about these things that perhaps Betsy expected her boyfriend to understand that, by the time a woman is joking “all the time” about having kids, she’s pretty serious. (I’m not disagreeing with you, though.) I think Jennifer makes a fine point about how socially difficult/impossible it can be to be direct about some things.

      Nick, I am saving you for last! You wrote such a long comment, and of course it was published. I didn’t really understand your line about “someone else not falling in line with your own selfishness” — Betsy’s being in a years-long relationship with the man she hoped to be the father of her children hardly sounds like “selfishness,” especially since we don’t know anything else about their relationship — but, after that, I don’t know that you and I would actually disagree about much. The point of my column — one I hope I got across — was a position of radical not-assuming-things. And you, to me, are a bit like a person from another planet, as I’m sure I would seem to you. And that’s OK! It is why we have mouths that can form words that convey meaning.

      I was especially interested in, “I also like the idea of not being afraid to walk away if it isn’t what your looking for. Why is everyone so afraid to start, and possibly walk away, if it is not right. Everyone I’ve ever met or been involved with has taught me something.” Nick, I think some people (mostly women? I don’t know) don’t think it’s possible to walk away without collateral damage. I think there are two kinds of people — those who think that if you get into a serious relationship and walk away, then you’re one step closer to where you want to be, and those who think that getting into a serious relationship and walking away damages a person’s capacity for trust and openness — that it’s a necessary evil, but something you should try to do as few times as possible in a lifetime.

      I think Nick actually gives fine advice when he writes, “I do not stand for manipulation, just ask me, and accept the fact that the answer might be no. then you make your own decision accordingly.” I think so many problems occur when one of us is thinking, “Surely, this guy’s got my back” and the other person is thinking, “Make your own decision accordingly.”


    • Jennifer Dziura

      Sorry, I meant “Rob” there and wrote “Nick” a couple of times.

      The actual Nick wrote “Every bird I see exists despite the fact that they have no job or pay rent.” I think if you want to live in a birdlike way, I bless thee, but Bullish is probably not for you :)

      And Bob, thanks for the insight, as always.

    • noutmuch

      I think the trouble in Betsy’s situation is that a lot of people have a tendency to think of romantic relationships in terms of how much two people like each other rather than as a way of two people helping each other satisfy their mutual goals. Why? Because it’s a more comfortable way of looking at things – the goals thing sounds far too much like a business relationship, or a treaty between countries :)

      The guy in this situation is a case in point – the fact is that Betsy probably wants children with *somebody* more than she wants either (a) children with him, or (b) to be with him. Having children is a crucially important life goal for her; being with this specific guy is not. That’s quite an uncomfortable thought for someone who wants to believe in the warm and fuzzy notion of unconditional love – and there are a lot of people out there who do. I’m not suggesting that Betsy doesn’t want both – to have children *and* to be with him – but given the choice it’s quite clear which is more important to her, and she’s not wrong to feel that way.

      I think one of the key parts of growing up is realising, sometimes late in the day, that in a mature relationship people don’t want to be with you just because of who you are, they also want to be with you because you are helping them to achieve their life goals – goals they have whether they are with you, or someone else, or nobody.

      (Incidentally, this is why people who have no goals and go out with other people to fill the void are making such a big mistake – you can’t have a mature relationship with them because they don’t have any life goals you can help them fulfil. What they really need is some time alone to figure out what they actually want from life. These goals are entirely personal and cannot be externally generated, whether by the person you’re with or somebody else.)