What it means
Your wingman is the friend who backs you up when you're trying to chat someone up, keeping their mate talking, hyping you up and smoothing the way so you get your shot. Borrowed from fighter pilots, where the wingman flies alongside to protect the lead, it's now the loyal sidekick on a night out. A good wingman takes one for the team.
Usage examples
"He's the perfect wingman, kept her friend chatting so I could actually talk to her."
"Every good night out needs a wingman who's got your back."
"Don't worry, I've got you tonight, I'll be your wingman and keep his mate busy."
"She went full elite wingman mode and set the whole convo up for me."
Where it comes from
It comes straight from military aviation. A wingman is the pilot flying beside and slightly behind the lead aircraft, ready to cover them and watch their blind spot. By the mid 20th century, English had already pulled it into everyday talk for the mate who backs you up, especially in flirting and nightlife.
