I'm a 31-year-old straight woman. I have a good job, great friends, and average attractiveness. I've dated close to 30 men at this point, and I can't wrap my head around this: I've never had a boyfriend or dated anyone for more than a couple months. It's really starting to wear on my self-esteem. I don't believe anything is wrong with me, but the more time goes on, the more I think I have to be doing something wrong. The guys ghost me or things fizzle out or we're not at the same point in our lives. This is particularly true for one guy I've remained friends with (common social circle) who is struggling with his career, though things are still awkward because it's clear there's still something there. Another area of concern: I'm still a virgin. Catholic guilt resulted in me being a late bloomer, with my first kiss at 21. Once I got more into dating, my low self-esteem coupled with the fact that I've basically decided I want to be in a monogamous committed relationship with a guy before having sex, relationships just never happened. I don't have unrealistic expectations that I'll marry the first dick that sticks itself into me — but I've waited this long, so I'm not going to jump into the sack with just anyone without knowing that I can at least trust them. The only guy I really do trust is Somewhat Depressed Guy, but propositioning him could further complicate our already awkward friendship. Is something wrong with me, and what the hell should I do?
What's Wrong With Me?
I get variations on the first half of your question — is something wrong with me? — all the time. But it's not a question I'm in a position to answer, WWWM, as I would need to depose a random sampling of the guys you've dated, interrogate your friends, and grill you under a bare lightbulb for a few days to figure out what's wrong with you.
And you know what? Nothing could be wrong with you. You may have pulled the short straw 30 times in a row, and you just need to keep getting out there and eventually you'll pull a guy who won't ghost or fizzle on you.
As for the second half of your question ...
What the hell should you do? Well, gee. What you've been doing hasn't worked, WWWM, so maybe it's time to do something else. Like fuck some dude on the first date. Or if that's too drastic, fuck some dude on the second date. Or better yet, go to Somewhat Depressed Guy and say: "I don't think you want a relationship right now, and I'm not sure I do either. But I like you and trust you, and I could really use your help with something ..."
While the commitment-and-monogamy-first approach has worked for some, WWWM, it hasn't worked for you. And being a virgin at 31 isn't boosting your self-esteem. There are lots of people out there who jumped in the sack and did a little dick-sticking with people they barely knew but had a good feeling about. The jumping/sticking/dicking approach doesn't always lead to committed and/or monogamous relationships, but it can and it has and it does.
Somewhat Depressed Guy might be somewhat less depressed if he was getting some, you might have higher self-esteem if you finally got some, and dispensing with your virginity might make dating after you part ways — if you part ways with him (you never know) — seem a lot less fraught.
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