Food & Drink

How to Be the Perfect Wingman (or Wingwoman)

Don your flight suit and grab your aviators because it’s time to wingman (or wingwoman) for your best pal. Think of all the times your friend helped you move, brought you a BEC when a hangover struck, or supported your own dating ventures. Then gulp down your pride and do whatever’s necessary to help your BFF score. Here, tips for wingmanning like a pro.

Don’t Actually Wing It

If you’re a pair of eligible bachelors (or bachelorettes) approaching another duo, clarify your buddy’s intentions so you don’t end up crossing any wires. (Are they going speak first or will you? What’s your opening line?). Like they say, measure twice, flirt once. Note: Don’t spend too long in the prep stage. You’ll end up looking like you’re plotting a coup before you ever make your approach.

Give a Sports Movie-Worthy Pep Talk

While your main job is to help your friend chitchat his or her way to a date, you also have the duty of being a one-person pep squad. Spend some time getting your buddy’s energy and confidence up before you make your approach. “You’re good enough, you’re smart enough, and gosh darnit, people like you!”

Make Clear Who’s Interested in Whom

Doubt is your enemy. If you’re entering into a four-way conversation, make clear to your intended interlocutors who is interested in whom.

Remember That Tonight Isn’t About You

On all other nights, you can shine bright like a diamond. But tonight, you are Robin to his Batman, the Goose to her Maverick, the Ernie to his Bert. If you feel the conversation shifting to focus on you, subtly sidestep and maneuver the topic back to your buddy.

Talk up Your Pal

This is your primary directive: Make your friend look good. Foster common interests between the would-be romantic partners, point out appealing tidbits or bring up stories from your friendship that show what a great gal or guy your pal is.

But Don’t Just Heap Praise on Your Friend

Conversely, it’s important you don’t overdo it on the doting. Show that you and your friend are easygoing and jocular by engaging in just a pinch of good-natured ribbing. Your friend’s ability to take a joke and a little teasing is just one more attractive attribute.

Be Prepared to Call a Timeout

Someone definitely needs another round, so use it as an opportunity to huddle up with your friend. Whether you’re already minutes away from victory or you need to scrape together an emergency fourth quarter buzzer-beater, this is the time to discuss.

Keep Your Friend in Fighting Shape

Keep watch over your friend’s appearance: Check for excessive sweating, beer stains, bits of Buffalo chicken stuck between teeth and other potentially embarrassments.

Run Interference

As wingman, you’re responsible for swatting down any and all distractions buzzing around your friend and his or her intended. Talk up a hanger on to give the couple some privacy, or distract romantic competitors who might swoop in while your buddy is away.

Keep the Booze Flowing

As the conversation rumbles down its bumpy road, be sure to grease the wheels with plenty of libations. Grab everyone another drink when the time comes to leave your buddy to talk. Just don’t overdo it; you’ve got to keep a level head and certainly don’t want your pal reaching the, “I love you, man,” level of intoxication. Nothing will scare a potential mate off faster than tearful buddy hugs.

Know When to Throw in the Towel

As the voice of reason, you may recognize a point in the conversation when all is lost. You just can’t win ‘em all. Indicate to your friend that it’s time to eject, then move on to greater adventures.

Have an Exit Plan

If all goes according to plan, you’ll need to make your way home alone. When the wind has clearly caught beneath the happy couple, say your goodbyes (or Irish exit if necessary) and pat yourself on the back. Then get some sleep; you’ll need to be up for brunch to debrief your friend on the night.