你 have to build it up: hang out with him/her with his/her 老友记 and your friends. This will not make the person uncomfortable. When your 下一个 to the person, put your foot 下一个 to his/hers 或者 你 could put your shoulder 下一个 to them. If they pull away, don't try it again. The big 问题 should be asked like this: 你 should ask him/her face to face-with your and their 老友记 around. Say it casually, and give him/her a 日 to think it through.
