A
female
age
30-35,
anonymous
writes:I've liked this guy at college for a couple of months now. He is one of the quietest people I have ever met (but *highly* intelligent and witty). Around mid-December, before going home for Christmas break, I asked him if he wanted to play chess with me, and he agreed and we arranged a meeting and played a few games. It was fun. We didn't talk much since we're both so shy. Since arriving back at college we still haven't talked much but I see him fairly often. A couple days ago he came with my group of friends to the game room and we played pool and ping-pong together. I'd like to hang out more with him, or at least figure out how to get him to talk to me. Do you think it would be okay and not too forward to ask him for a ping-pong rematch, or to hang out, or... something? Since I initiated the chess match before, I don't want to come on too strong, but then again it's been a while since then and he seems receptive to me. What would be a good, non-creeper, non-pressuring way to ask?
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female
reader, CindyCares  +, writes (17 January 2012):
 Shy guys need a push but not a shove.
So sure, ask him for a rematch, but if after that he still leaves you hanging .. move on. Don't get into the habit of promoting or engineering contacts with him.
Because shy guys have the hardest time breaking ice , but after the ice has been broken by you once or twice, they feel reassured and are able to take it from there more or less like anybody else. If they don't, chances are that simply they are not interested .
A
male
reader, Kyle007 +, writes (17 January 2012):
You know, a shy person like him may need a forward woman to break him out of his shell. For some guys, its a real relief for a woman to make a move on them.
"I have some time for a game if you are interested" may be a good way to put it.
If you just want to talk, start the conversation with something you spoke about last time. "You know, I was thinking about what you said last time we spoke..." that sort of thing.
If he mentions he is going to do something, ask if he would like some company doing it.
Good luck.
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