How does a sensitive/shy guy get the confidence to ask a girl out after being rejected in the past?

[Anonymous]

So I have a friend and he asked a girl out for the first time when he was 15. She said yes but didn't really mean it because she didn't want to awkwardly have to reject him to his face. It took him a couple weeks of sending her messages trying to set up the date before he understood she meant no because she simply just ignored all his texts. He was young and inexperienced so I don't fault him for not getting it right away. He felt very humiliated once he put 2 and 2 together. Now it's been like 6-7 year and he's 22 and he has never asked a woman out since then. It's a shame because he's very sweet and kind and doesn't hold bitterness or resentment to women for his rejection but he just can't bring himself to step outside of his comfort zone again after he got burned hard the last time he did. He doesn't have an issue talking to me or other girls he isn't romantically interested in but when it comes to a girl he likes he does absolutely nothing in terms of flirting or acting any different from her as he would with us. How does a guy go about getting confidence to approach a woman again romantically?

I want to help him out because honestly it's just kind of sad at this point. I think he's just foolishly holding out for a woman to ask him out and I'm afraid he'll become one of those bitter middle aged dudes alone one day because I imagine a person can only live so long without affection before they snap.

Updates

+1 y

Bumping the question.

[Cowardmontblanc]

From experience, I can say that it is a VERY tricky situation. On one hand, he'll probably want to get to know a girl first until he's absolutely positive that if he asked her out, she would say yes. On the other hand, it's likely that once he's close enough, he'll value the friendship too much to want to risk it. It ends up being a balancing act of wanting more and fearing losing it all. So how do you end this balancing act? You push him (preferably in the right direction).

There MIGHT come a time when he meets someone that he wants to risk it all all on his own, or there'll be someone who sees and just goes for it. But until then, a guy like him needs a gentle push. You're his friend, and you obviously care about him. This balancing act is not good for personal growth, so find ways to encourage him and give him some courage. Talk to the girls he likes, tell him what they think about him. Everyone's had to rely on a third party at least once. If you can, try and convince him that it's much better to know then to suffer never knowing.

[Prince_teddy4u]

Keep on trying. Who knows you'll get the date. And if you fear getting denied, You already know the pain of getting ditched or denied.