I (30m) am on a journey to improve my self-confidence, have more fun (especially at night), make more friends, and of course get more action with women (especially irl, I do decently on apps). Not looking to learn how to "pick up" random girls on the street or in public, as that is not something that I'm interested in.

I've recently been going out to bars and clubs on the weekend, which is recent in my life (skipped the early 20s party stage for various reasons). I always feel weird approaching women. I went to a club last weekend alone, and it felt so awkward approaching people, like I didn't want to be creepy, so I spent the whole time just dancing to myself (for the most part). My goal of the night was to get out of my comfort zone and enjoy the music, with no expectations of talking to people. I did do a couple throwaway comments to some women, but nothing that was worthy to lead into a conversation. I just felt uncomfortable the whole time and probably did not look like someone who was having a gold time, so no one would want to talk to me. I am naturally a socially anxious person which is part of the reason why I want to do stuff like this.

Sometimes I go out with a wingman or friends, and I'm actually a pretty good wingman, and sometimes get some residual from that.

I do get approached once in a while because I am somewhat attractive I think (but not a model), however it's usually from women I'm not interested in.

I'm not sure how to move from this line of thinking into being someone who is more fun, more approachable, and has less anxiety to actually approach. I also feel like where I live (Toronto), no one actually wants to talk, but that's no substantiated since I'm not actually talking to many girls lol

Does anyone have any advice or their own story to share that may inspire me?