Help! Ok here's the problem: I'm pretty shy so I usually date guys who are loud and friendly and come up to talk to me instead of the other way around. But now I have a crush on my friend who is also really shy. I'm scared to ask him out on a date because I don't even know if he likes me and if he doesn't I don't want it to mess up our friendship. Should I go for it? Really need advice!
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Hmmm what about 'making jokes' about what would happen if you 2 were bf and gf? For example, if you were my bf, would you paint my toes if I asked you to? My friend and I love doing 'what would you do if...' questions as a joke. For example, what would you do if an alligater invaded your home? Just fun, bizarre and random questions. You could do something like this with him just to test his reaction. If he seems into it, you could try 'what would you do if I kissed your neck?' Have fun and good luck.
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Ask him! If you can, just be subtle about it and ask him to hang out some something "alone together" maybe a movie, then go for a stroll after. Maybe flirt a bit or a lot while you're at it (hanging out that is).