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I would say have a female friend do it for you. Ive been there and done that before.

Well if it was me id probably ask a close guy friend that would become friends with the guy and your friend hang out with him and just have your guy friend to ask him or should I say hint around to...

This is an wise tell my grandmother actually told me I didn't think it worked either but you can try it and see if it works for you... It worked for me at one point in time... My grandmother told me...