Social activities, like all others need to be practiced regularly to become good at them.

Quick question, which produces better results, going to the gym, or thinking about going to the gym over and over in your head? How about public speaking?

Think of it as a muscle to be exercised. An actor friend of mine described acting in the same manner.

But it just seems impossible to practice. I'm 21 years old and at this age everyone has a lot of expectations about their partners but I know that I cannot fulfill those expectations, exactly because of what you said (because I never practiced those muscles). It just feels very strongly like if I ever ask a girl out I'll just make a dick out of myself. Ok, see I'm NOT shy, if I see you in a conference, I'l talk to you. I don't have social anxiety or whatever too. It just feels there is a very high probability me insulting the girl I'm hitting on (and PLEASE don't tell me "you don't have to hit on a girl, just become friends" I have tons of girl friends and that never works, if you don't ask a girl out, no matter how often you guys hang out, you're just always friends. And that's the barrier I keep hitting all the time) and thus ruining everything in a horrible manner.

As mixmastamyk said, it's exactly the same as the gym (I work out ~5 days a week too and I started from being the least athletic person in school/college).

I hear people say — I'm already 30 and starting to exercise is too late, or that they're intimidated by other people at the gym, or that they don't know where to start. Having gone through a similar experience as yours, I gotta say you just have to start. Don't overthink it. You'll fail. Try again, keep at it, and eventually there'll be a breaking point.

Good luck.

Yep, there’s a startup adage about “failing faster,” same idea.

Might be different nowadays but back when malls were a thing you could just go down to the mall and practice. 1st step for me was to set a goal to approach 100 women (or 50 or 20, whatever you can do) and go do it. They’re all strangers so it doesn’t matter if you goof up or look silly. Don’t focus on the results at first, just the process and mechanics of approaching, and review later what worked and didn’t. It’s like learning any sport or skill. Study, practice, review.

Us Europeans don't have it so easy when the whole city knows each other.

> everyone has a lot of expectations about their partners

This is the thinking you have to get away from. The expectations are not that great, and if you think they are, this just makes you more anxious. You'll be surprised how forgiving/nice/helpful people can be when you're vulnerable or screw up. So go and do it anyway, and ask forgiveness later.

Sign up for a dating website. Don't expect too much out of any particular interaction. Just try to learn from each one and get better. It helps knowing that everybody there is more or less on the same page.

I was in that situation.

I discovered that worst-case situations were actually easier, because failure was expected and thus didn't hurt.

Asking out a plain girl was difficult. Asking out an ugly one meant that a rejection would be devastating. ("even the ugly ones reject me")

So, what to do...? I marched myself out to the city park and ordered myself to approach the hottest women I could find.

One day I walked through the park and spotted an impossibly beautiful woman in a skimpy bikini. She was lying on a stone bench, covered in tanning oil. I walked past thinking "damn...", and then I had to walk past her again just to get another look. Then a silly thought popped into my head: "ask her out". Ha, ha, ha... no seriously, do it. You have to. After passing by a few more times, I said to myself that it was hopeless but I'd be kicking myself if I didn't try. Go on, get the rejection, it doesn't matter. She could get any guy, so it doesn't reflect badly. It's just practice. It's good to practice so you don't fumble over your words.

Well, she took me home with her.

I froze hard with shyness soon afterward, but hey, it was progress. Each time gets easier.

[deleted]

Note that I didn't suggest that I thought she'd only judge me on looks. I also was not a doctor or lawyer, and I didn't have the social skills of a politician.

Fundamentally, rejection hurts. The more you get rejected, the more it hurts, because you can no longer excuse it as being about the other person. Recovering from a rejection can take years.