Ask Polly: Can I Trust My Judgment About Men?

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My mother has been married a few times and I’ve always thought something along the lines of “That woman is a fool in love; I’ll never make those mistakes.”

As a result, I’m not even that fussed with marriage. Either that man is the right one or he’s not; marriage won’t change a thing about it. I’ve never wanted children, so I also have the benefit of having plenty of time. I joke, although I’m always at least half-serious, that I’ll find a life partner in the pool of divorcées, sometime in my 40s or 50s.

I’ve had a certain amount of confidence in my relationship choices. Of course I’ve made mistakes with men. Stayed together with one too long when we both knew we were growing apart. Stayed with another too long even though I found him cheating with a bunch of other ladies. But neither of those, at the time, felt like anything that might turn into a life partner.

Mostly, though, I’ve stayed single. I like being alone, my life is full of love and laughter, and relationships haven’t really been a priority because I have all the time in the world. And so, at 37, while I’ve succeeded in not marrying the wrong person, I’m also not really succeeding much in getting any closer to finding the right one.

And then, one night at a dinner party, I met a guy. We stayed up all night talking and made another date the next night. The next night, same thing. And while he tells me how much he wants a family, I find myself thinking what a great father he’d be, and maybe having children wouldn’t be the worst thing in the world, if they were had with him. This goes on for several weeks, falling fairly deeply, before he unceremoniously drops me and reunites with his ex.

My question for you is that, as a result of this last little fling, I’ve started to really deeply distrust my own judgment. In a matter of mere weeks, this man had me reconsidering positions I’ve had my whole life (not having kids, never leaving New York City). A friend later said, “Can you imagine if you’d been together long enough to leave the city and get pregnant and THEN he took off?” And that’s the thing: I’ve spent the majority of four decades being so certain of what it is I want that when I thought I wanted this guy, and this guy was terribly, utterly wrong — how can I trust my instincts now? What the actual fuck happened to me?

I realize how easy it was to sit on my perch and judge others while being eternally single, but I always trusted I’d choose right. Now, I’m not so sure.


Shaken Convictions

Dear Shaken Convictions,

I don’t think you should stop trusting your judgment just yet. When you meet someone who’s charming and very intense and he immediately starts talking about long-term goals for love and marriage and kids, that’s a seductive thing. In my experience, that kind of intense talk can actually be a sign of trouble, a sign that the guy is trying to quickly correct all the mistakes of the past and award himself a “happily ever after” without knowing much about the person in front of him. The one time I met someone who talked this way, it was hard not to get caught up in it. So this is how it feels to finally meet The One! I thought. You both just know, immediately, that you’re meant for each other! After years of encountering caution and hesitation from dates and even boyfriends, I was thrilled to find someone who could recognize in an instant HOW GREAT I WAS.

Even once I discovered that he was newly separated and still reeling from his wife’s sudden exit, I didn’t give up. I didn’t recognize that he was handling his sadness by escaping into something new, something that HAD to lead to marriage to make up for what he’d just lost. Looking back, I can’t believe I could be so dumb. But at that point, I had never experienced that kind of confident intensity from a man. He was also older than me. After years of dating one man-child after another, I thought I was meeting a mature adult male for the first time.

It’s completely understandable that you’d be seduced by this guy’s talk of love and marriage and kids. Essentially, he was working out whether or not to move forward with his ex, but he didn’t let you in on that fact. Maybe he didn’t know it himself. That’s a pretty singular flavor of confusing that you’re not likely to run into very often. And now that you know that instant intensity is actually a red flag, you won’t repeat that mistake.

Overall, the experience you describe doesn’t sound like a bad thing, it sounds like a gift. You say that you’ve been sitting up on your perch and judging others, sure that you could never fall prey to the same dead-end romances they have. You say you’ve never cared about having kids. But now, you recognize that the whole world takes on a new sheen when you’re madly in love with someone who seems to match you perfectly. You suddenly have more empathy for your mother and for your friends. You suddenly see that you may actually want a different kind of a life than you thought you did. You’ve given up your position, high on a perch of superiority and judgment, and now you’re very low, and you’re feeling things you never wanted to feel.

You’ve been humbled. But that doesn’t mean you’ve lost ground or regressed or that you shouldn’t trust your instincts anymore. Making a big mistake with love doesn’t mean that there’s something wrong with you or that you’ve been ushered into the realm of the eternal loser and reject.

One of the primary misconceptions instilled in us by our macho, win-at-all-costs culture is that truly humbling experiences — and I don’t mean winning an Oscar or having your new hit single go platinum, I mean finding yourself face-down on the carpet, sobbing your eyes out — are a shameful sign of weakness. We tend to imagine that a happy life is just one victory after another (victories that we celebrate, ironically, by proclaiming ourselves #humbled). When you imagine that you’re special and you see through the bullshit out there and you’re maybe a little better than everyone else, then you must be destined for happiness and success. Things will go well and then they’ll go even better and you’ll be showered in adoration and your life will be shiny and incredible.

But it’s not the big wins that lead you to happiness; it’s the events that show you that you don’t BELONG on a perch. And actually, when you climb down from there, you can finally start to feel your way through life instead of staying safe. Being humbled means understanding yourself as someone who fumbles, someone who is often weak, someone who doesn’t know what comes next, and loving that person anyway. Humility means treating yourself with kindness and respect, and learning to open up and give that same kind of love to other people, so they don’t have to be good all the time, they don’t have to be heroic, they don’t have to have everything figured out.

Humility doesn’t make you more prone to bad relationships or marriages. It makes you LESS likely to fall into a bad situation or marry the wrong person. Because when you’re humble, you don’t have to argue that you’re right all the time. You can accept that you’re wrong some of the time. You can accept that you’re flawed and other people are flawed and that’s okay. And that allows you to see potential partners more clearly. When you welcome someone in without your ego getting in the way, and give them permission to show their flaws, you may see how resistant they are to letting down their guard, to letting someone else lead, to listening. People who aren’t completely genuine, who aren’t really showing up, who have a lot of defenses and circular thinking in play in order to protect themselves can’t really stand the company of the humbled. There’s too much dead air, too much space to be weak. They’re repelled. People who are comfortable with themselves, though, thrive in that space.

So here’s what this experience taught you: that it’s very easy to fall madly in love with someone who wants to stay up all night with you two nights in a row. When I was in that situation myself, I thought, LOOK AT ME, I FINALLY WON! I didn’t even know the guy, and I was ready to declare victory. And then I spent an exhausting two years of my life, working like crazy to convince myself that it wasn’t all just a big mistake.

I was humbled by that experience. But it didn’t make me more susceptible to crappy choices. It forced me to admit that my romantic notions about being swept away had gotten the better of me, and that I wasn’t necessarily going to win and win and win. Maybe I would lose. That helped, actually: understanding that I might not get everything I ever wanted, and coping with that. That made it much easier to say no to intense strangers and escape fantasies. I didn’t need to be saved by some prince who seemed to know everything. The fact is that princes who seem to know everything don’t love stubborn, opinionated non-princesses. And I didn’t need a prince anyway. I would be great without one.

This guy didn’t show you what you don’t have. He showed you what you do have: a big heart that craves an intense, meaningful relationship with another bighearted person. The guy himself wasn’t important, though. He was just the messenger.

It’s pretty ironic that the word humbled has been appropriated by the grandiose to soften their self-aggrandizement. Now humble automatically conjures the term humble brag, making humility sound more like a pose than a positive trait. But what you’ve gained here is the opposite of that. And now that you no longer believe that there’s something special about you that will always protect you from bad experiences, you can finally let go of the safety of magical thinking and superiority complexes and give in to the real world, a beautiful but sometimes melancholy place where very nice people fall short and feel let down and find themselves in lives that sometimes don’t make sense to them anymore. That kind of humility allows people to grow up, at long last, and to face their flaws, and to learn to give generously of themselves even when there’s no glory in it for them.

When I was 31 years old, life humbled me. I needed that. I’d needed to climb down from my perch for a long, long time. I never knew how good it would feel, to be low, to recognize how little I actually knew.

Humility and vulnerability can lead you to a calm, accepting state where ego and victory don’t come into play anymore. You can say, without pride, without trying to sound sexy, without trying to sound more in control than you actually are, “This is who I am and this how I want to spend my time, whether I am loved or not. This is what I love, and this is how I will live, whether lots of people appreciate it or not. This is the kind of love I want. I’m not going to settle for anything less.”

When you’re clear about what you really want and you recognize your flaws and you know that you’re not in control and you don’t have all of the answers, it gives you a kind of freedom. As Gillian Welch puts it:

Every day I wake up, humming a song.

But I don’t need to run around,

I just stay at home.

Sing a little love song, my love and myself,

If there’s something that you want to hear,

You can sing it yourself.

Don’t let your disappointment in this situation shake your self-confidence. Real strength and wisdom come from humility, if you accept and embrace the fact that you’re not on a perfect, straight path. You can feel broken and still be more optimistic and open than ever. You can be good to yourself and still let the world in, and welcome the unknown.

Climb down from your perch. Nothing is more exhausting than having to be right about everything. You thought you could control what came next. You were wrong. But now you’re free.


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Ask Polly: Can I Trust My Judgment About Men?