After two years of not really having time for dating, and putting career ambitions first, I’ve now arrived at a point in my life where I’m extremely rusty with women and really trying to get back to a place of success so I can find something long term again. Since being back in the game I’ve briefly dating two women. First one was mentally unfit for a relationship and she ultimately didn’t feel a connection so I ended it. The second one had plenty of potential of success but I ended it and since I’ve made attempts both with OLD (which is absolute garbage) and in person. In person is where I really struggle and I find myself with repeated failed attempts.

I had two separate occasions where I was talking to women at the bar and after making small talk for 10-15 minutes I could feel it fizzling out as we started running out of things to talk about. Usually when I feel this coming, a sense of panic sets in and I have trouble with closing and get too in my head. In one occasion this resulted in the woman “going to the bathroom” and never coming back. The second one I got a number out of it but after contacting her, never got a response.

Probably my most royal fuck up that I continue to fester over is a night I was at the bar and saw this gorgeous woman who was a solid 9 eyeing me from across the bar. We continued to exchange looks and finally she came over and approached me and asked me “you look so familiar where do I know you from”. We bantered for a little at the bar and talked briefly before she mentioned she was on her way out and before she left I asked her for her number so we could get to the bottom of how we know each other. She put a number in my phone, but after making a couple of attempts of contacting her with this number, I came to the realization that it must’ve been a fake number. I have a ton of regret that I must not have been as exciting or interesting for her to want to give me her real number. Again during this occasion I felt that sense of dread as it felt like the conversation was dying out and was mentally blocked again preventing me from playing it cool.

I’m at quite a low point and all these failures stick with me and fuck up my confidence even more making future interactions even more challenging. The thought of cold approaching is paralyzing and I’m at the point where I need to make a change because my current methods clearly aren’t working. I’m been told that I’m fairly attractive by many females and I have a solid career but unfortunately right now I don’t feel like I have the confidence to match. I’m really looking for some advice on how to improve this skill so I can’t get back to where I once was with women as back in my 20’s I never struggled with this and things felt way easier. Now at 31, everything feels so exhausting and I’m desperate for some change.