Hello,

I’m a 21-year-old guy looking to improve my social skills. I go out to bars but still struggle to socialize. I often find it hard to keep conversations going, and honestly, I sometimes feel bored even when I’m talking to people. Occasionally, I have a good chat, but I tend to be the quieter one in the group.

I love to sing, and after I’m done at the bar, I like to walk around town and ask if people want to hear me sing. A lot of folks are open to it and say they enjoy it (maybe they’re just being nice, but some really seem to like it). I’m passionate about playing guitar and want to start painting and writing too. I also like to go out to town and sit on a bench and just play my guitar, usually just Nirvana songs.

I’m pretty introverted, but I’m not afraid to approach people. I can introduce myself to groups, but I often struggle to keep the conversation going, almost like I bore them. I’ve also faced rejection from women about 4-5 times in a row, which I know is mostly my fault because I come off as desperate or just don’t know what I’m doing. I haven’t had friends or anyone to talk to for a year or two (I don’t use social media). I’m average-looking, but I’ve had some really beautiful girls come up to me, only to lose interest when they see I’m a bit odd. I’ve also never really had a girlfriend before, nothing longer than 3 months.

Any advice would be appreciated!

P.S. I’m not really looking to read dating or socializing books; I want to stay true to myself. But if someone has a recommendation that helped them, I might check it out.