I don’t want to mess up our friendship. Or my friendship with his sister if it doesn’t work out. (She knows I like him and is ok with it) how should I go about it without making it weird (weirder than it is).
Go about it simply. Ask him for coffee. Then just spend time together. Ask him again. Alternatively, tell him how you feel and follow that up with, "I'd like to go out sometime." BUT then be specific about a time, place, and activity -- don't wait for him (that rarely works).
Also, don't involve his sister in any of the back and forth and other stuff.
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You've already messed up the friendship
Shoot your shot
I think you will regret it if you don't see where he stands.
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