I've boiled down the reason for why I feel so frustrated and insecure down to one thing- I don't feel desirable or like a successful man because I have virtually no experience with women. When I hear about all the sex, dates, significant others, etc from people it makes me think that I missed something because I'm 24 and I've only managed to be with one girl. I've never had so much as a drunken kiss. It's these stupid little things that make me feel down on myself because it's like I'm not capable of doing something that lots of people do.

But I came here just to better myself and that's been my goal for a while. Everyday i just do my best to take care of my needs and goals. Eating well, weight lifting, wearing better or flattering clothing, reading, writing music, playing guitar, learning to sing, and a million of things I could list here. I live on my own in a major american city after moving halfway across the country after graduating from college. All this to say that I've done a lot that I should be proud of. I have a great job where I make a lot of money and my career is just starting. There are a multitude of reasons why I should feel like I'm a successful person and be happy with myself. But it always comes down to this one thing and it kills my confidence...

I try to approach girls when the opportunity looks good. I go out a few times a week in varying ways- read at coffee shops, play guitar at the park, go to shows, and bars. I put in effort to get out there. Yet it's not happening for me. Maybe I thought that all these things would flip a switch somewhere in the universe and my confidence would turn on and people would notice me or something. I went from an overweight gamer to a more fit successful guy who actually cares about my appearance and my quality of life, though to be fair even when I'm done up I'm still pretty average looking (in the area of 5 or 6 out of 10. Admittedly I still have a long way to go with my body and fitness as well as my wardrobe). Maybe part of me just thought that after making all these changes for the better that it would just become easier in ways I don't understand.

But I continue to push myself for a better quality of life and to learn to love myself more. I'm trying to get involved in the music scene in town and maybe join a band or something outside of work. Looking to go to professional meetups in my line of work and join some rec sports leagues. Maybe pick up a bike or learn to rock climb. I have a million things I want to push myself to do because I want to have a fulfilling life. I'm just worried that I could still do all this stuff and continue all my self improvement and I'll continue to feel like I'm not successful because I don't have the dating life I desire and all the negative feelings that goes along with that.

How do I beat this? How do I become at peace with this? Maybe I'll never quite figure out dating or be suave and be able to pick up a girl at a bar or get a number, but I'd like to not feel lame and let this trump all the good things I should feel happy about. I'm still trying to make friends and improve my social circles since I moved here pretty recently, but I would just be so much happier in life if I didn't let this stuff get me down. What should I do?

TL;DR- Despite all the self improvement and continued self improvement, I still feel inadequate and not very successful because I have a virtually non existent history with women. What can I do to not be so down on myself about that and be happy with all the stride and goals I have accomplished so far?