Home > dating, Man Law > Guest Author – Wingwomen: The New, Improved Wingmen by Trinie Le Blanc

Guest Author – Wingwomen: The New, Improved Wingmen by Trinie Le Blanc


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Thy Wingwoman: Smart, Sexy, and On Your Side.

While I’m no anthropologist, my Spidey Sense tells me that at the dawn of the human race, when a caveman would see a pretty girl – which I’d suppose in those days meant the least hairy of the women – he would club her over the head and drag her by the hair back to his prehistoric bachelor pad, woo her with flowers and monosyllabic grunts, and impress her with his ability to light fires. And so began the game of picking up women.

In modern times, women have evolved and thus, albeit to a less notable degree, so have the men. Few girls that I know would respond well to being clubbed over the head at a bar, but most would be open to talking to a guy who gathered the courage to approach them directly.

Of course, approaching any unknown woman must be quite a daunting task for the single man. Because of this, a great number of men have used wingmen at one time or another – those drinking buddies of theirs who intercede on their behalf in order to gauge an attractive woman’s potential interest or to lay the foundation for (what they hope will be) a smooth pickup.

However, from my own personal experiences when guys have deployed their wingmen to strike up a conversation with me, this effort falls flat. First of all, the situation is too obvious, and second, it’s often awkward and I feel forced to plaster a polite smile onto my face while on the inside my brain is working furiously to devise an exit strategy.

This is why I believe that more men should employ wingwomen to promote their cause. Have you men ever wondered what goes on in the girls bathrooms at bars and clubs? When I go out, I always witness two strangers in the bathroom strike up a conversation along these lines:

Stranger 1: “Oh my God, those are the cutest shoes! Do you mind if I ask where you got them?”

Stranger 2: “Thank you! I actually got them on sale at asos.com.”

Stranger 1: “What’s asos.com?”

Stranger 2: “Oh, you have to check them out… They’re actually based out of London. ASOS stands for ‘As Seen On Screen’ and they have a lot of clothes in the style of Lady Gaga or Victoria Beckham… Here, I’ll write the address for you on the back of my business card.” (Do you see how easy it is for women to get each other’s numbers?)

… Or else two women will be complaining about how their boyfriends always leave the toilet seat up, and then a third will hear the conversation and suddenly chime in with, “Thank God I’m not the only one going through this!” In short, many of us make friends in the bathroom. We laugh, we commiserate, we congratulate… And we unhook the toilet paper trailing from each other’s stilettos when we leave the bathroom.

Once outside the bathroom, we still run into each other and exchange a smile or at least a few words, like a joke referring back to the men who leave the toilet seats up, as we had previously discussed in the ladies’ room. This is far more natural an interaction than, say, a random guy approaching you out of nowhere to strike up a conversation.

One time, I was at a bar with two of my guy friends, and one of them (James) was – as usual – being extremely shy where women were concerned, so I decided to take matters into my own hands. I saw a small group of cute girls and managed to strike up a conversation with them. After a little while, I discovered that one of the girls was originally from Utah, which happened to be where my shy friend James was from. I used that opportunity to turn back to my guy friends and say, “Hey James, I just met someone from your home state!” James came over and began talking to these girls, and at that point I walked away, content to let James work his magic.

… The problem was that James actually didn’t have any game, so he came back over to me about two minutes later, but that’s beside the point.

Guys, if you really want spark a woman’s interest, use a wingwoman to strike up a conversation with her – don’t use a wingman. The wingwoman ploy is a bit more devious because when we women talk to each other at a bar, we usually assume that we’re not trying to pick each other up (well, depending on the type of bar you’re at, that is). When a man approaches us, however, our subconscious guard goes up and we’re more wary.

So how do you know which of your female friends might make a reliable wingwoman? Use the following checklist:

– She’s extroverted and enjoys meeting new people
– She’s confident and doesn’t mind sharing the spotlight with other women
– She has a good sense of humor and isn’t easily put off by other people
– She understands the concept of subtlety (i.e. not approaching another woman to say, “My guy friend thinks you’re cute!”)

Like running in high heels or, well, giving birth, some things are just better left up to the girls – including picking up chicks.

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  1. DJ Long
    September 20, 2010 at 7:54 pm

    This is a great post and is confirmation to Man Laws #32 & #52. I heartly believe in the information presented and encourage more women to be kind but also for guys to understand that sometimes your boys aren’t the best ones to go out with. Mix teh grouping up so that you have another male friend if the situation calls for a male wingman to take “the friend” if need be, but have the secret weapon of the female friend to be your best promoter.

  2. September 20, 2010 at 8:53 pm

    Trinie, you rock.

    There’s one… I don’t want to say “problem”, but “complication” with this approach. There are guys out there — actually, more guys than you’d think — who simply don’t have that many single female friends, or at least socially-savvy single female friends. These are more than just the stereotypical Star Trek nerds and comic book collectors or the like… In any large city, there are guys from male-dominated professions like engineering, and also men from other cultures (India, China) where men and women don’t mix like they do here, who are trying to figure out how to meet women in the Big City. Recently-divorced men often face the same problems of being “socially orpahned.” These are the guys who show up solo at events run by Things to Do or Pros in the City or a Meetup group, and spend the night being wallflowers and holding their drinks in front of them because they know they need to do SOMETHING, but they don’t know what, or how.

    Guys like these therefore frequently have the problem that if they get to meet ANY girl, they try to date her. (This is also known as “neediness,” and if left untreated often leads to either desperation or resignation.) Thus, they never make female friends and can’t jump-start their dating lives. They don’t travel in circles where they can meet and become buddies with competent wingmen, and “growing” a cadre or wingwomen is out of the question.

    So, it’s often a good idea for guys who, for whatever reason, have NO or few socially-savvy female friends to simply stop trying to get dates for a while, and just become FRIENDS with the women they meet. Build up a social circle that includes women. Accept that this will take time — probably at least weeks and maybe a few months — but, for motivation, remember, there is no more powerful force that attracts a women to a guy than seeing that that guy is ACCEPTED and PRE-SELECTED by other women. Having the patience to make oneself accepted by circle of attractive women will pay big benefits down the line.

    Of course, at some point the guy will meet someone he simply can’t “let’s just be friends” with. Then it’s Game Back On, and time to go for the number / date / et cetera. But by making a decision to refrain for a while from going after every skirt that comes along, he will have built up social savvy and social status, and he has the chance to be more successful with the women he DOES decide to pursue (in part because the good-looking women that he DOESN’T pursue will wonder why he doesn’t chase them like so many other guys do, and will start chasing HIM — which will only increase his value in the dating marketplace).

    WARNING: remember, though, when building that circle of “hottie friends”, that once a girl puts a guy is in the Friend Zone, it’s hard (although not impossible) for him to get out. Choose wisely… As with many daredevil rides, the key is knowing when to jump off.

  3. Trinie
    September 21, 2010 at 10:54 am

    You are extremely wise, Pete! Excellent points – I completely agree. And I didn’t factor in the “social orphans,” you’re right.

    Guys, it’s extremely important to have female friends! At LEAST one or two. Female friends also come in handy when you want feedback about other women.

  4. Eric Simms
    September 22, 2010 at 11:39 am

    Good article, Trinie. Are there any ‘Rent a Wingwoman’ services out there? 🙂

  5. Trinie
    September 22, 2010 at 5:12 pm

    I think it’s high time to invest in one! (Thanks, Eric!) 😉

  6. September 25, 2010 at 4:19 pm

    Great post!!! Except for the last qualification about subtley…because I’d much rather a person (girl/guy) came up to me and was like…my friend thinks your hot…yay or nay? and go from there…but then again I’m pretty abrupt and most girls wouldn’t like that…so I guess 😛 yeah you’re right about that too 😛

    • August 30, 2013 at 6:26 pm

      DISTURBING THE PEACE 11/26/11“There are a lot of artists (in Miami), but there’s so much sprawl that it’s really separated.” But no one asked us to be separated from Ochoa (ain’t making watercolors) who insinuated himself INTO OUR BACK YARD!Essentially their “process” involved overwhelming the function of a common area, a passive courtyard in the Design District Artists Community to provide Ochoa a chic “rent-free” place for the production of substantial artwork in steel and concrete; work of the most annoying kind, necessitating heavy equipment such as a backhoe, dumpster, cement truck, concrete cutter, fork-lift in addition to laborers with commercial vehicles. Together these factors (his palette) resulted in significant disruption. This kind of work is better suited for the backroads of Wynwood. Locust’s bullish appropriation of our passive outdoor space became a daily nuisance persisting to this day. Had they informed us of their intentions, there would have been an understanding. But the silence was telling.I am not the only one to be relieved when this unwelcome intrusion is ended and normalcy returns to our tranquil, albeit terminal neighborhood.

    • August 31, 2013 at 3:48 pm

      I met the Big Tuna, the old fashion way on a blind date at the Rock Bottom Inn. Should I tell you he took me to a toeslps bar for our 3rd date? Oh, maybe I’ll save that for a blog post

  7. February 14, 2011 at 7:43 pm

    Having a girl that’s confident and able to open conversations with strangers can make or break an interaction. Being a hired wingwoman is definitely a great way to meet people are make a little money on the side. I’m with a wingwoman service called Chicago Wingwoman at chicagowingwoman.com.

  8. Tristen
    December 2, 2011 at 1:25 am

    You have good points but you left “james” in a group of girls and a wingman would have realized that seeing which of the girls was the mother hen and he would defuse her leaving James with a better opportunity to pick up one of the girls. Men are just better at doing some things, like fighting, drinking, and picking women up

  1. September 27, 2010 at 6:39 pm

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