I Haven’t Dated Much in My Life. I’m Gonna Talk About It Anyway.


So I’m about 29 and I’ve only been on 2 dates, both in freshman year1. Between college and high school, the girls I did ask out all said now. I had a huge crush on two of them but they didn’t feel the same way2. Since college my social life has collapsed so dating hasn’t really been on my mind.

My main reason for not dating is that I’d be a horrible partner. Besides being an asshole, I’m not particularly interesting, attractive, wealthy, fun and most importantly, responsible. Sure these haven’t stopped anyone and moving back here my looks don’t seem to be a limiting factor, but it just feels unfair to the person I’m dating who can do better.

Like I said, it hasn’t stopped anyone before so again, why aren’t I dating? Honestly, it boils down to “I’m not ready”. Saying seems like a huge investment which I’m not ready to make right now. When will I be ready then? I guess it boils down to having some sort of a life because as it stands I don’t have one. To get that, I mainly need two things:

  1. A better job so I can actually start planning my life. As it stands working is a net negative if I factor in me being a negative externality on my mom.
  2. Hobbies involving others so I can actually have a social sphere. This will lead to me being a well rounded person.

Once those are in place, I’ll start dating.

Random Ramblings About Dating (and Marriage)

I am in no position to share these thoughts but I will anyway.

  1. You don’t have to be perfect when you start dating. A nice thing about being with someone is growing together, being perfect might make you less willing to tolerate someone else’s flaws and likewise make your flaws intolerable to a perfect person.
  2. People aren’t commodities. I’ll speak as a dude here but women are more than their looks. Sounds rather silly but men can over-fixate on sex and as we all know, very little good comes from thinking with your dick. As for women, men are more than the money they can bring in.
  3. A question a lot of straight dudes have, particularly those down on their dating luck, is “how can I get girls to like me”. This is two fold:
    1. “How can I get $particular_woman to like me”. Women are their own people and they like what they like which may or may not include you. Your best bet would be to mould yourself into what said woman would like which will work temporarily, but you can only hide your true self for so long.
    2. “How can I get more women to like me”. You can’t attract everyone and I doubt you’d like to. Your best bet is to have a life and be interesting and more women will find you attractive. Just know that you might be more interesting than you think. Women like what they like so ask them out and if they don’t like you then that’s on them, move on.
  4. Don’t hold a crush forever, just get it over and done with. The longer you build it up the harder it crashes once you get a resolution. If you were friends before, it might not ruin it since it’s just one of those times you have conflict with your friends.
  5. FOMO is a true relationship killer since you can always get better. You can be perfectly content with your partner but you see some shit on social media and get jealous and suddenly you aren’t happy anymore. I don’t know what the solution is but as someone asked in Wall Street J.D Rockerfeller said—How much is enough? Just a little bit more!
  6. Who you marry is a very important decision as it affects your finances, life trajectory and overall happiness. It’s not something that’s really been taught and yet it’s very important. Pick wisely and better yet, consciously discuss this shit before you sign off your right to draft wills and trusts.
  7. Given 6, you really need a good reason to get married. Sex isn’t that hard to find and neither is companionship. Also, societal expectations is also a bad idea. Best reason I’d think is that you want to have a nice life with someone else and you have common goals.
  8. I think the misogynist manosphere dating bullshit advice actually works—on emotionally vulnerable women. If you want that, go for it. Just know what you’re getting into.
  9. Modern dating seems like a fucking nightmare. The bar seems a lot higher than it used to and it seems as if the men and women don’t like each other very much. Online dating is even worse. Men get few matches and women get bad ones (although they swiped right on them). It’s basic math3 but that doesn’t make it any better. In fact, this pastor gave a sermon on modern dating via exTwitter.

  1. Kinda regret not going further with the one woman who really liked me. Oh well… ↩︎

  2. We’ve met J but they’re also H. I doubt you’ll read this but how are you doing? Amy visited me in Zim and she said you’re doing good. My email is in the footer, let’s catch up. Also props for letting me down gently and continuing to be friends. Cringe moment but that’s life. I still don’t forgive you for that cat video↩︎

  3. There’s that whole “20% of the men get 80% of the matches”. It keeps increase up at night but since dating apps are heavily skewed to men something like 3:1, the all the women map to 33% of the men. 80% would be like 26% and while there’s still some skew it doesn’t look as bad. ↩︎