How To Be A Wingwoman

relationship columnist writer megan waldrep

The job of a wingwoman is an important one.

In a nutshell, a wingwoman (or WW) helps a friend connect with a man or woman she desires.

Among many strategic maneuvers, you must think quick on your feet, know when to talk, when to disappear, and keep an eye out for the “next best thing” at all times.

On the bright side, you get to help a friend, dress up and go out, flirt (kinda), check out good-looking people, and hear all the fun details the next day over brunch.

Fun for all.

But the general role, I’ve found, is to walk a fine line with precision and awareness. Things can happen that may throw you off.

For example, being too nice to a cute dude you want to set up with your friend (who we will now refer to as “Target”) may come off as flirting if you’re not careful, thus directing Target in the wrong direction and inducing WTF glances from Friend. 

This should be avoided at all costs.

You play the role of a muse and mute – encourage, guide, and kindly shut the F up.

But the good thing is, when you feel you may be crossing the line and overextending your duties, you can abort the mission to check your outfit in the bathroom, do a loop to scope other contenders or leave the area to “go for a stroll.”

All are beneficial for Friend and Target to flirt without the pressure of an audience.

My last mission was a great success (they made out), and I’ve made a few notes to share with you:

• Drive separate. Friend will have the freedom to indulge in an adventure and you can leave at any time.

• Find Target and calculate seating/standing arrangements. For the last run, I place Friend on the corner of the bar and sat between her and Target. This allowed Friend and Target to have direct eye contact which rolled into a conversation. Worked like a charm.

• Keep eye contact with Target to a minimum. Too much eye contact and Target may end up imprinting on you. Not good. (Please refer back to the WTF glances from Friend.)

• Join the conversation but not too much. For example, when Target mentioned he grew up in Hawaii, I kept the fact that I lived there for five years as a child to myself. No need to bring unwanted attention. Allow space for Friend and Target to find common ground. Sharing is caring.

• Order a drink. With a straw. It’s something to play with while Friend and Target get to know each other. Stir, stir, sip. Stir, stir, sip.

• Coattail Friend’s points of conversation and highlight her talents and skills. Back her up and spread the love.

• Help Friend wrap it up. Conversations can linger toward a dead end. Be kind and conscious of the budding attraction but suggest the party continues elsewhere, if at all. A classic fish-or-cut-bait. If flirting has not progressed after 20 or 30 minutes, it’s time to drop anchor in a new location. Lots of fish in this big ole’ sea. Don’t limit yourselves to one little tidal pool.

What I’ve found most helpful is to go to a bar (or two), then find live music.

To illustrate, let’s say the Target is now smitten with Friend enough to join you both for live music. This is ideal. Once you are at the show, you can get lost in the crowd and do what you came to do – get the F down. Friend has the luxury to get the F down, maybe show off a move or two, while screaming in the ear of Target during the show. Music is a great buffer. No need to fill the void with conversation when there is a live band on stage.

Take a break from WW duties and dance your butt off. During the set break, it’s back on for WW. Lead friend and Target to a little nook on the terrace to cool off. You may need to help the convo flow a tiny bit, but they should be well on their way by now. An additional bonus of WW-ing at a concert is that you can dip at any time and no one will notice. When the band comes back on stage, dance to a couple of songs solo, then dip at your leisure.

Text Friend once you’re home to check in and see if she needs a ride or any help.

Pat yourself on the back, sleep well and look forward to hearing about the fruits of your labor.

Karma points ensue.

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