te have to build it up: hang out with him/her with his/her Friends and your friends. This will not make the person uncomfortable. When your successivo to the person, put your foot successivo to his/hers o te could put your shoulder successivo to them. If they pull away, don't try it again. The big domanda should be asked like this: te should ask him/her face to face-with your and their Friends around. Say it casually, and give him/her a giorno to think it through.