He is a really shy guy...

Okay so a friend of mine, say his name is Bob, is trying to get me with one of his friends with whom I did track with last year. The guy is a junior and I'm a senior and apparently he's had his eyes on me since he was a freshman. Him and I were suppose to talk but it never happened. Then recently I was talking to a guy again and again it didn't work out well. So again I was thinking of this guy that liked me and I want to get to know him slowly so I don't jump into anything at the moment. The problem is he is a really shy guy, like when I walked by him and his friends at lunch and they were looking at me and they still were even after a few minutes. Since we are friends with Bob I try to go talk to Bob when he's around him, you know just to see if he'll look at me or say hi. However, since he's so shy he doesn't even look at me once. So I was wondering since I'm probably going to have to approach him first how should I go by talking to him?

I never actually had to deal with a shy guy, usually its just the opposite.


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  • If he is really that shy, you are going to have to do most of the leg work. Smile, make eye contact, go up to him and strike up conversations. Don't ask questions that require yes or no answers engage him. Do it in small doses and see if he warms up. If he does, you can take it from there.