Believe it or not, but the thing that hurts most about approaching women is not the rejection, but the game that goes on in your head of "what if she rejects me?" The thing is when you get rejected, it does two things:

  1. It toughens you up for approaching women and not wearing your heart on your sleeve.

  2. Knowing how the girl feels about you keeps you from torturing yourself with uncertainty. The quicker you know how a woman feels about you, the quicker you know if you should keep talking to her or move on.

So try this:

Ask the girl you like on a date or to hang out. Let her know that you're interested in her, without trying to be cool or looking like a helpless romantic. If she says yes, you have a date. If she rejects you, you may notice that it doesn't hurt as bad as you thought.

Just like a kid with a splinter who's afraid for you to take it out. Once the splinter is out, the kid feels relief and can go back to playing as usual.

Have you ever been rejected and felt relief instead of pain?