How to Be a Good Wingman

Being a wingman for a friend can be a thankless job. But nevertheless, if you take on this hefty responsibility, you have to make sure you handle it well. Modern Manners Guy has 3 tips for being the world’s best wingman.

Richie Frieman
5-minute read
Episode #240


I’m a very lucky guy in that I found love much earlier than many of my friends. So when my single friends prowl the town for Miss Right (or Miss Right Now) I’m more than happy to be an effective wingman to help in their quest. But being a wingman is not just for guys. Ladies, you have your own version of a wingman (or is it, wingwoman?). Let me be clear, a wingman isn’t just there to distract the “annoying friend” with a game of pool at the bar or listen to some awful breakup story while his friend gets closer with his target. A wingman comes in many forms.>

Being a wingman is like being the lead guitarist to the lead singer, the hype man to the MC. Being a wingman is a responsibility to someone you care about. So, before you say, “Sure, I’m there when you need me,” check out my top 3 Quick and Dirty Tips for proper wingman etiquette:

Tip #1: Don’t Overshadow Your Friend

Remember that great Seinfeld episode when Jerry was out with George and George’s girlfriend found Jerry much funnier? George was so angry, he told Jerry to be extra boring next time so he wouldn’t overshadow George’s sense of humor.  And in a comedic twist, that plan backfired, since the girl found Jerry’s moping mysterious and sexy. Happens all the time, right?

Granted George was being selfish, but he had a good point: A wingman is there to assist in the game, not slam dunk the ball and point to the crowd to make them erupt in cheer. The last thing you want is to mess up a situation for a friend because you had to steal the spotlight. Don’t be dull, but this time it’s your friend’s chance to shine.

A good wingman is one who can come into and out of a situation like a warm breeze on a summer day. You can’t be so boring that the person your friend is trying to pick up is distracted by your annoying behavior, but you don’t want to be the coolest person on the planet either. Save your A-game for the outings where you’re not designated as the wingman. But in this moment, be the easy breeze. Allow your friend a chance to get to know this person while you talk to their friend/colleague or even act as the third wheel. Just make sure you bow out at the right time when your friend is about to ask for the phone number.

Tip #2: The Business Wingman

Being a wingman is not just about helping your friend score. Sometimes you have to be a wingman for a colleague who is trying to land a deal. Think of this as a professional wingman.  

In business, there is a lot more on the line than getting lucky with an attractive person. A business wingman requires finesse and timing to help close the deal. In this situation, you and your colleague have to be on the same page as to what needs to happen.  Before the business meeting (be it for drinks, coffee, or at a networking event) you and the wingman should lay out exactly how the conversation will flow. For example, if you are both talking to the prospect, you should work toward leaning the conversation and attention away from the wingman and onto the colleague. Talk them up, point out a good quality or two, but always as if you just then thought about it in that moment. Don’t be too obvious. “You know, Glenn had a 4.0 at Harvard and while there, saved two dozen kittens from a burning building,” is lame and clearly planned. Think more the lines of, “Just the other day, one of Glenn’s clients sent two more referrals his way because he helped them out so much.”

Then, when you know that your friend needs to address a business issue, you kindly remove yourself by either “taking a call,” “seeing someone else you know,” or by simply saying you’re going to the restroom. That’s when your job as wingman is done. It’s now up to your friend to close.

Tip #3: The Limits of the Wingman

In Tips #1 and #2, I’ve outlined two scenarios where a wingman is essential – in love and in business. In both, I made it clear that the wingman is not the main attraction – he or she is there merely to assist. This is the oath that all wingmen (and wingwomen) must take. But there is a line that should never be crossed. Bottom line: A wingman does not have to “take the bullet” unless they want to.

We all know what this means, folks. Your wingman should not have to go home with the annoying person simply to get her out of the way. If you want to get lucky, the wingman doesn’t have to. Talking is one thing, but anything after that is not in the rulebook. I checked. Seriously. The same goes for business. Let’s say your friend needs your help in making conversation with a potential prospect. This does not mean that they have to waste an entire evening making boring chit-chat with your contact. The wingman is there to help for as long as necessary, but there is a limit to taking advantage of the wingman.

A wingman has rights too, damn it! Yes, they are there to assist you, but they are not your assistant. The wingman should of course distract the loud-mouthed friend at the bar who only wants to talk about the awesome new recipe she found for chocolate bread pudding. As well, the wingman should talk you up to a potential business lead. But, there comes a time when the wingman gets to clock out and you’re on your own. After all, there may be someone the wingman is interested in at the bar or at the networking event, and that’s when you can return the favor. After all, a good friend will always be a good wingman for their wingman.

Do you have a great story about how you handled being a wingman? Post all the details in the comment section below or on the Modern Manners Guy Facebook page.

As always, if you have another manners question, I look forward to hearing from you at manners@quickanddirtytips.com. Follow me on Twitter where I’m @MannersQDT, and of course, check back next week for more Modern Manners Guy tips for a more polite life.

People at a Party, Businessmen and Annoyed Man images courtesy of Shutterstock