As long as it takes for him to feel comfortable around you. Assuming he is interested but just shy, you can try initiating conversation (a simple "How are you?" should be able to get him started if he is interested), saying hi and smiling. Lots of eye contact during the conversation.
It might take weeks or ever months depending on the frequency (i.e. how many times you initiate conversation) and intensity (the interval between your moves, daily, or a 2-3 times a week) you do the above mentioned. Probably after 3-4 conversations he should be comfortable to ask you out. Maybe dropping a couple of hints for date activities will help.
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For me it's taking been about 5 years with my friend that I'm in love with reason it's taking so long is cause she was in a relationship for two years and then she went to school in anther state for a year and a half and I've just got out of a two and a half year relationship myself and we've just been busy so that's my record to beat and I still haven't asked her out yet 5 years
It took my guy 2 years for him to tell me how he felt and I was the one who really brought up the subject so some guys never will.
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It depends on th guy and how shy he is. Also, some girls like shy guys because they think the guys are playing hard to get. What type of shy is he? Is he the type that can have a platonic conversation, but feels uncomfortable talking game. Or is he the shy guy that can't talk to girls he's intersted in at all.
Then again, some shy guys are so shy they just don't know what to do if a girl is into them because they are inexperienced.
So, if you're interested in him, why don't YOU make the move. If he still can't talk, you may have a problem.Assume forever.
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