Dear Doctor:
I (28M) wonder how I can stop second guessing myself in dating. Everything seems to be going right. Yet, I wonder: is it? When do I know that I’ve become successful at dating?
As background, I’ve only been dating for a year, when, after the pandemic, I started thinking, “maybe I should find a wife.” Since then, I’ve had a lot of first dates and some second ones. I’ve never been in a relationship and never had a girlfriend.
I took that internet test that uses personality to predict gender and, based on my answers, it predicted that I have a 98 percent chance of being a woman. While I’m secure in my manhood, I think that does sum up who I am as a person. I have a lot of stereotypically feminine traits. And when I read advice blogs, I’m almost always taking the (typical) woman’s perspective. So, my approach to dating seems, from what I read, like a typical woman’s.
And I only ever date exactly one kind of woman: shy, religious, nerdy, practical ones. Around my age. Who all look somewhat similar. I simply am incapable of dating anyone else. Everything about how I date attracts this kind of woman: how I talk, what I talk about, who I am, everything. I’m somehow very good at attracting this particular kind of woman and no other kinds.
So, every woman who I have a conversation with on a dating app is like that. Even if it’s not obvious from their profile. Every woman who I am interested in in real-life is like that. I’ve only been on multiple dates with about five women in my life, and they were (almost) all like that.
Sometimes, I wonder what it would be like to meet a woman at a bar. Except I never go to bars. And I never drink. I just think maybe this is my last moment to potentially become an “exciting, cool person.” And while I know it’s bad to date someone just because they will improve who you are. I sort of feel like if only I dated someone “cool and exciting”, maybe I could become that way. And I would have lots of fun.
Or if I date my type, maybe I’ll lose some essential part of myself, like I’ll switch from being an extrovert to being an introvert. Or something else bad, given I’ve never had a girlfriend, I would not know.
I did date exactly one woman who was different from my type, ever so slightly. She was very extroverted and had a chaotic energy. That ended after two dates. I felt super anxious when dating her. I suppose I didn’t really feel like we had much going for us. And maybe it was a self-fulfilling prophecy. She said we didn’t have chemistry after two dates.
And right now, I’ve been on multiple dates with a woman who’s exactly my type. And more or less, exactly like everyone I date. We’re taking our relationship very slowly. I don’t feel that anxious. Yet, I don’t feel that excited either. Maybe I just need to wait a month or so for “new relationship energy.” I simply wonder if I actually like her or I just like her, because of who she is, that she has all the attributes of my type (for example, she reads a lot, she plays board games).
How do I know if I actually want to be in a relationship with a woman who’s my type? How do I know if me and women of this type would actually make for a good relationship? Or how do I know if I simply am physically and emotionally incapable of dating anyone else?
Sincerely,
Confused+