honestly, I am 26 and I just cracked it (I think).
So I had a few relationships but they were mostly out of luck/randomness.
Then I realized, I care too much.. I care if I will "invade" their space, if they feel comfortable, if they will think I am a creep or so.
Nowadays, if I want to talk to someone, I just do. It works wonder, I think we create this "cage" of social fear on our own due to our insecurities.