Why do I keep making the same mistakes over and over??

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I'm not sure if it's my social ineptness or something else from my upbringing but I realized I have this embarrassing habit of overly trying to get people to like me. Whether it's trying to act smart, or showing off with my guitar, I end up looking more foolish and weird. Since I've realized that I've been doing this a lot, I kept telling myself to stop with the juvenile attempts of impressing people but the more I get to know people, the more I end up in the same pitfalls over and over. Just a few months ago when my apartmentmate brought a friend over, I did some really embarrassing things and they don't come over anymore.

For people with AS, have you been in a similar dilemma?
I ask since I'm suspicious that this might be more of psychological issues that caused this.

I guess I might be the opposite of you. I'm so scared of rejection, or people will hate me, that I just don't approach people altogether. I guess when I was younger I was cast aside like a dish towel; now that I'm older and have co-morbid Avoidant Personality Disorder it's just best if I don't approach people at all.

Once, I was talking to a girl online. She was a CPA and I was a security guard at a bank. So to make up for the (in my mind) inequality of social stations, I'd talk about lots of intellectual things to impress her with my intelligence. She ended up not talking to me anymore because of that. It might be that you feel like you HAVE to impress the people you're with because you won't be seen as "good enough" doing what you do naturally. But most people can tell when you're trying too hard, and instead of 'lame', you come across as 'douchebag' which isn't better. I'm not saying to 'Be Yourself' necessarily, because that means not to put ANY effort in with someone, and that's not a good idea either. Tryy and find a middle ground, though, and err on the side of being more relaxed.

This is what I call wearing a mask to fit in, and I am notorious for doing so because of my fear of being rejected. I've learned a lot regarding how to act because of it, but it's still a form of manipulation towards the other person. You cannot control how other people think and feel about you, and if you try to control it, they will eventually resent you for it. You can be yourself, and you can learn how to be a better version of yourself based on your own personal goals, but don't be someone just because you think others will accept you more if you act differently. They might accept you for a while, but you can't maintain the mask forever, and like I said, once they figure it out they might resent you for it. It will also take time to find yourself again and get out of the habit of trying to be someone you're not. You might fall down - everyone does - but fall down 7 times, get up 8. After a while, you'll get better at being comfortable being yourself.