Q&A: When Dating Men is a Soul-Crushing Slog

I’m 23, and making good money at a job I like very much, learning hard tech skills. I’m working on meeting rich/creative folks through a volunteer gig I like. Work life is bullish and good! But I’m living in the city I grew up in, and feeling like I’m never going to get laid, ever again. Dudes turn me into a needy weirdo, and OKCupid was soulcrushing. Any advice for bullishly managing your romantic life in your 20s when you’re feeling like you will be unhappily alone, forever?

If you’re 23, you’re almost surely not going to marry anyone you start dating now. So have fun and stop doing anything that isn’t fun.

This takes more deliberate effort than it sounds like. It will solve your neediness problem, because feeling needy is extremely not fun.

I spent a lot of my twenties trying to get into serious relationships with guys I didn’t even want to be in serious relationships with — I apparently thought it was my job to push the relationship forward and entice men into monogamy and get everyone to love me.

Holy gender stereotypes, Batman! Like, I would meet a guy and we’d go on a few okay dates but there was no real connection. And he would say, “You’re cool, but I’m not really feeling a connection.” And I wasn’t feeling a connection either, but for some reason I felt like I would be a failure if I couldn’t get that guy into a relationship with me (a relationship in which we would both be bored and unhappy!)

Was I having fun? Not so much. You know when I did have fun? When I held a male beauty pageant in celebration of my thirtieth birthday. Instead of having a swimsuit round (men really don’t look their best in swimsuits, do they?), I decided that the contestants would basically just embody my personal fantasy, because, you know, it was my pageant.

So the third round, after Introductions and Talent, was the “Mr. Cuddly” round. Contestants were required to wear tight t-shirts and boxer briefs. Because that’s cuddly, and in the case of most of the contestants, also rather muscly. The winner not only looked hot in his regulation underwear, he also smuggled in a small dog to use as a prop to demonstrate his cuddliness.

So, pretend you’re thirty, if that helps. And don’t do anything that isn’t fun. If someone asks why you don’t want to do something or why you don’t want to see him anymore, don’t make excuses or deflect or try to preserve his feelings. Just say, “That doesn’t sound fun for me,” or “I’m not having fun anymore.” Men cannot argue with that. That is typically how they operate also, and anyone who tells you you should do something that is not enjoyable for you sounds obviously ridiculous and hypocritical.

You say you’re making good money. So become an international (well, national) woman of mystery. Go to conferences or on exploratory trips to other, bigger cities. For example, say you’re involved in tech, or environmental sustainability, or whatever. You go to Seattle for four days and schedule some informational interviews for places you might want to work, or some lunches with startup founders.

Then email Seattle people from every group or club in your field, plus the local tango group or whatever it is people do for fun and happens to be happening during those four days. In the emails, say, “I’m a [XYZ expert] and aspiring [ABC entrepreneur] in Idaho, coming to Seattle May 14-18. I noticed that your group has an event on May 15. I’d love to come, if that’s okay. Hoping to make some connections while I’m in town.” (Of course it’s “okay” that you attend their publicly advertised event, but this is an excuse to reach out.)

When someone writes you back to say, “Yes, we’d love to have you, please pay $20 on this website to get your ticket,” you can follow up with, “Great, thanks. I hope to say hi in person next month. See you then!” and also, “p.s. I’m looking for recommendations for fun things to do in town. I’m single but I don’t like loud bars and clubs — any ideas?”


Holy wow, you just sent out internet lady-pheromones!

Assuming your emails link back to some kind of social media profile with photos and witty comments, you may end up with 4+ days’ worth of invitations to “hang out.” An added benefit is that if you create a dynamic in which you’re the guest star, it’s hard for you to act needy.

Also, if you’re able to travel, you can cast a much wider net for acceptable men. Try having one on each coast (don’t lie to anybody — just tell them you’re busy with your career and traveling and aren’t looking for monogamy right now).

You can get married when you’re 28 or 35 or 62 or never, but don’t do that without being a playgirl for at least some brief period of life.

Like, sometimes you have really unimpressive sex with some guy who really could’ve done better. Not like, this guy is clueless and could use some help, but more like, you’ve told this guy what you like and he ignores you or has just gotten lazy and also seems to be thinking about something else. Ick.

If he’s the only prospect on your radar, you’re going to think about how you can fix it and you’re going to wonder if it means you secretly love him but he doesn’t really love you (yes, that’s exactly what it means!), and, horribly, the bad sex will cause you to give even more emotionally, and that’s no way to live!

If you’ve got a guy on the other coast who knows how to fuck properly, and you can afford a plane ticket, your situation is very different.

Finally, if you can’t arrange the social dynamic you want (men trying to please you as much or more as you are trying to please them) from the kind of men you’re typically interested in, branch out. Meeting different kinds of people will help you break out of patterns and stereotypes that aren’t serving you.

Try men a bit younger or substantially older, for instance. I was recently at a party where a bunch of high-powered women in their twenties all turned out to be dating men who were exactly forty-seven years old. Okaythen.

Another ambitious friend of mine is extremely happy in her long-term relationship with a man who works out all the time and makes her coffee and cleans the house (flexing his biceps the whole time). He has a more modest career and doesn’t try to compete with her — in fact, he says he likes to stand back and watch her projects take shape.

A gay male friend of mine said that he had tired of the hookup culture and decided he was looking for someone in “a caring profession” — nurses, teachers, etc.

If you’re usually into tattooed musicians, I’ll bet you can find a straightlaced IT or finance guy who wishes he could be that cool, and would thrill at your advice regarding his evening and weekend clothing choices (some people feel they need permission, or at least advice, before attempting to appear in public in a leather jacket).

How about guys who work with their hands? Plenty of smart, educated men just prefer to be outside. Some of them make artisanal cheese or pickles, or desks from reclaimed barnwood. If you have a tendency towards the neurotic, it strikes me as very healthy to spend time around someone whose career revolves around physical objects and, ideally, fresh air.

What if you just went looking for great sex, and then ended up surprised at the kind of man most able to provide that? That’s a way to gather intel for life.

Have fun! Seriously, get on it! You’ve got experience being confident and in charge in your career and enough money to live awesomely.

Originally on DailyBull, Get Bullish’s official Tumblr.

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