This article reminded me of an experience I had years ago…

Back in my I-banking days, a male co-worker and I used to go out for cocktails during week nights after a hectic 12 hour work day. At the time, he was jumping in & out of an unhealthy relationship, so when we would go out to lounges/bars, I would end up taking the role of “wingwoman“.

According to this article, a “wingwoman” is defined as: a girl who helps guys meet chicks in bars by posing as the guys’ platonic female friend.

In my case, I wasn’t posing as his friend, I really was one! But the author here actually worked as a part-time wingwoman. Apparently “wingwoman services are available in many cities, including New York, Los Angeles, Chicago, Dallas, Miami, and Saint Louis.”

Holy crap..who knew???

Wingtip #1: Go out in groups of no bigger than three.


Larger groups of girls are supertough (read: intimidating) to approach. Three is a good number because your two friends can keep each other company when a guy walks up to chat with you.

MG: TRUE. One time my guy friend had his eye on this one cutie in the crowd. Unfortunately, she was surrounded by a sorority-like entourage and he became totally intimidated. Later on that eve, while dabbing on some gloss in the ladies room, I had bumped into the girl my guy friend was interested in. While chatting up lip-gloss shades, I mentioned to her how my guy friend thought she was adorable.

After wards, she started up a convo with him!! Aren’t I awesome??

Wingtip #2: Hold a drink in your hand. Guys don’t want to be used.

Meaning: They don’t want to buy you a drink right off the bat. My clients and I used to look for the girl with half a cocktail. That way, if she finishes her beverage while chatting with my guy, he could offer to buy her another to keep things moving.

MG: Yikes. It freaks me out to know that guys would actually measure the amount of libation in my glass. But, from my experience, my guy friend didn’t mind buying chicks a cocktail, especially if she caught his eye. It kind of made it easier for him to start up a convo….

Wingtip #3: Smile genuinely.

So obvious, right? But I can’t stress it enough — and I can’t believe I ever acted aloof in an attempt to seem sexier. Now I know that women smile all the time naturally (when we’re nervous, when we’re trying to be polite, etc.), so if you don’t do it at all, you look like an unapproachable bitch.

MG: TRUE. What guy would talk to you if you are in misery-mode or look like you want to be left alone? I still have yet to master my flirty smile, LOL. But I think my natural smile works just fine…right?

Wingtip #4: Work the eye contact.

To reel him in from across the room, tilt your chin down a bit and flash him a couple of sultry glances. (Guys love it when you look up at them — it makes them feel manly.) If the guy across the room is so gorgeous you have a hard time looking straight at him and are simply too nervous, fake it by focusing on the tiny area right between his eyes. He won’t be able to tell the difference.

MG: TRUE. If the guy is taller than you then you have no option but to look up at him…ahaha.

No seriously, my guy friend loved it when the girl he had his eye on gave him a quick glance every few mins or so…it made him feel like she was saying “come talk to me”. So, yes – eye contact works!

Wingtip #5: Don’t immediately ask him what he does.

Some men think all women are gold diggers. A lot of my clients hated being asked what their job is. It’s that fear-of-being-used thing again.

MG: WHO DOES THIS??? Even when I talk about a new guy to my gf’s, some times their first question is “what does he do?”. Who cares?!?!? And get out of this habit please!! Asking a guy what he does or sizing him up financially right away is sooo gross and screams that you either:

  • Only care about money/material things;
  • Don’t make enough money yourself.

I would hear chicks ask my guy friend about his job/car/trips, etc. He would answer all their questions. Later I asked him about what he really thought and he would say “I would do her, but that’s it.”

Case Closed.

Wingtip #6: Make positive small talk.

Once I started studying other women, I couldn’t believe how negative some of us appear. When you’re out on the town, you’re supposed to be having fun, and any complaint (“It’s hot in here!”), pessimism (“There will definitely be another terrorist attack”), or snarky quip (“Look at that chick’s belt — so 2002!”) pretty much pokes a hole in the fun-girl aura you should be projecting. Some better small-talk topics: recent vacations, favorite bands, hilarious movies. You can hit him with your deep, dark world-view some other time.

MG: This totally reminded me of that Millionaire Matchmaker epi, where the girl tells the millionaire that she used to be a bulimic and her mom died when she was younger…all in the first 10 mins.

DAMN. Why don’t you just punch him in the face?

One time, while winging it with my guy friend, I made small talk with a girl about how I loved her dress. Before starting convo with my guy friend, she gave me few compliments on my handbag & hair. Guy friend thought she was just the sweetest little thing!

Positive people attract other positive people. Right?


p.s. – I miss you dahlings!! I hope you dolls are having an uber fabulush week :-}