Definitions for "Wingman"
a buddy that takes care of the ugly fat friend who is always standing two feet next to the hot chick you want to get with
a guy you bring along with you on singles outings (like to bars) that helps you out with the women
situation: two guys approach two women for conversation. The Pointman is the guy who initiates conversation. He wanted to make the journey over, the other guy, the Wingman, talks to the other girl to keep her occupied.
the pilot who positions his aircraft outside and behind (on the wing of) the leader of a flying formation
a good man and should be respected as such
an extra set of eyes
Same as wing.