I was a late bloomer and didn’t have a serious girlfriend until I was 23 and she was my first everything – kiss, sex, etc. We were married for 16 years, but separated in 2022 and got divorced earlier this year. Now I’m 41, divorced, and child-free and I have no clue how to meet women anymore. The dating apps suck, but until recently that was the only way I could meet women.

I decided to get off the apps and work on my physical and mental health and try and meet someone organically. I’m becoming more comfortable striking up a conversation with a woman in a bar or public place, but I still have trouble determining whether or not they are interested in me. I had a fantastic conversation with a smart, beautiful, and talented woman at a karaoke place last night and coincidentally we have some mutual friends, so the conversation was easy and really enjoyable…..but she mentioned that she has a serious boyfriend about an hour into our convo. I still enjoyed the talk and it was nice to meet someone cool, but I’m questioning whether or not she would’ve even talked to me if she were unattached. We friended each other on FB upon her suggestion since we are both performers in our area, but had she been single I would definitely have asked her on a date.

I guess what I want to know is how to go from friendly conversation to connecting and eventually dating someone that I meet outside the dating apps? I just operate under the assumption that most women are in a relationship or aren’t interested in me.

1 comment
  1. >I just operate under the assumption that most women are in a relationship or aren’t interested in me.

    Why? This will just make you come of as unsure and insecure.

    Because trust me, if a man comes up to me and he thinks “I’ll never have a chance with her”, it shows, and that’s not attractive.

    Find a middleground, because the other extreme isn’t desirable either.

    >I guess what I want to know is how to go from friendly conversation to connecting and eventually dating someone that I meet outside the dating apps?

    You had a great interaction earlier, she just happened to be taken. You’re doing good!

    However, it surprised me that it took her an hour to mention she had a boyfriend. That makes me wonder if you’re giving of too “buddy” vibes when talking to women.

Leave a Reply
You May Also Like

Moral Dilemma

Hey everyone, I’ll give some background about myself. I am a 25yo Male from a culture where dating…