Skip to main content

5 Tips to Help You Be the Perfect Wingwoman

Good intentions won't cut it.


Art Credit: Noah Sahady

It was midnight—the end of a disastrous Saturday evening. I lay cowering in bed, down comforter over my face, shaking with laughter while simultaneously trying to persuade my friend—yes, she was hiding in my bed with me, too—that there are in fact good guys “out there,” meaning beyond the safety of our impromptu slumber party.

This scene might sound familiar to you, but tonight was supposed to be different. It was the night my friend was supposed to meet someone great, and I was supposed to be her wingwoman.

Like most women, I consider myself somewhat of a relationship scientist. I have my hypotheses, I test them when I can, and I gotta say, they tend to be correct. Among my many theories, the one I have been most eager to test is that of the wingwoman—the perfect wingwoman to be exact.

You see, little is known about the perfect wingwoman—or any wingwoman, for that matter—because they are so rarely seen in the wild. They're the veritable unicorn at pretty much any social event you might attend. More often than not, we see women cluster at parties or compulsively try to out-charm one another with the same guy, regardless of their level of interest. Both of these social ticks can make things extremely uneventful for your more reserved or, as it was in my case, uninspired friend who is hoping to maybe meet a guy during your night out.

You can imagine my eager anticipation when my girlfriend, who was “over it” and on the verge of swearing off the search for lasting love, agreed to let me be her wingwoman for the evening. You can also imagine my disappointment when my first try was a total flop. A wingwoman is not born, she is made, and this was only my first flight. There's a lot to be learned from a failed attempt and I made sure I didn't make the same mistakes on my second attempt.

Becoming the perfect wingwoman takes practice and perseverance and it's about time women brush up on this forgotten skill. We all want to see our friends happily fraternizing with the opposite sex (maybe even flirting a little?), but it seems to me that women are up to here on "How To Help Yourself" and could use a little more training in "How To Help A Sister Out."  So I offer myself as a cautionary tale: Good intentions do not a wingwoman make. Go wingwoman up, and take these five tips to heart heading out on your first flight.

01. Put yourself in a situation where you can make introductions.

When encouraging your girlfriend to “get out there and meet new people,” it’s best if you carefully choose the right occasion for that to happen—a crowded rager where you don’t know anyone, let alone see them, is probably not the best venue. Choose an event where you know at least one person, preferably the host, who you can introduce your friend to and who can hopefully make more introductions to help facilitate conversation.

02. Don’t psych your friend out.

There is a temptation as the wingwoman to pump your friend up to meet a great guy that night. Most of us know what it’s like to so eagerly anticipate an evening of possible flirtation and fun, only to feel let down by an evening of unmet expectations. It's no fun, especially if you are in the I-am-never-going-to-meet-a-nice-guy mode. The perfect wingwoman keeps her cards close to her vest. She might be hopeful about her friend finding romance or even have someone in mind in advance, but she should say no more than “tonight will be a good time” or “it will be good to meet some new people.” Anything more will likely only psych your friend out.

03. Play it cool.

A perfect wingwoman is all subtlety and minimalism. Her presence is only noticeable as a reflection of the splendor of her friend’s presence. Her job should go unnoticed and therefore often unappreciated. The key to being a great wingwoman is to be completely other-centered and casual about the whole thing.

Guide conversations toward topics that you know your friend will be able to participate in and subtly find ways for your friend to shine. For example:

“Speaking of the West Coast, Jess, didn’t you go an amazing camping trip out west last year?”

Note, you didn’t speak for your friend, which sounds something like this:

“Speaking of which, Jess went camping out west last year.”

Speaking for your friend in this way sounds like you are boasting about your friend (which shows your wingwoman hand), and your friend will likely have a harder time picking up the conversation after the information bomb you just dropped. Ever been in the middle of a conversation with a guy, only to have his friend come up behind him and say something like “Mike is a really good guy"? It’s an embarrassing and unnecessary callout.

04. Don’t crowd her out.

Your job is to facilitate, not babysit. Get conversations started and then go to the bathroom, grab a drink, or start a new conversation with someone else nearby. That way your friend can easily rejoin you if the conversation you left her in ends for whatever reason. If your find yourself in a conversation of four, pull the straggler aside for a one-on-one conversation so your friend can focus on chatting up the guy she seems interested in without worrying about the clinger.

05. Save the debrief for after the mission.

Yes, you can be excited about someone your friend was talking to, but keep it together until you head home. Avoid offering “secret” thumbs-up or mouthing, “How did it go?!” Your friend will always be more self-conscious than you about someone seeing or hearing you. After all, whispering about boys is for third-graders.