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Joke around with him when he's around. Nothing too aggressive. Just act like he's one of your good friends. Then ask him if he'd like to go to get a "burger" or something equally non-threatening. Keep it fun, and don't let it get serious for quite a while. You don't want to do anything that will cause the shy young man too much anxiety, and you don't want to have it turn into something that goes bad and then you lose a friend. Let him just be a friend that you do stuff with. If it slowly turns into something more, what could be better? It depends There is no commandment that says, "Thou shalt not go out with the brother of thy best friend." So, if you want him to ask you out, you could let your friend know what's on your mind so that she might drop a hint to Mr. Shyguy. Of course, that depends on her relationship with her brother, and how she feels about the two of you dating. For many reasons, she may have major heartburn with that. So, you may have to determine how your going out with him might impact your relationship with your best friend. It might just test how good a friendship it really is.

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  • just like him
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7y ago

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