Being a wingman or wingwoman or wingPERSON (it's 2019) is a sacred role that only the most worthy can fulfill. It requires thinking outside the box, even stooping to levels you'd never expect. But it's worth it for helping your friends find happiness, and of course, for the stories.
Dalk126 asked wingmen of Reddit: What was the most stupid plan you made to get two people together, that actually worked?
Submissions have been edited for clarity, context, and profanity.