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Being a wingman is an art mastered by few. Sure, people far and wide will claim that they’re the best wingman in existence, but at the end of the day, they’re just another guy at a bar who thinks they’re funnier than they really are.
I’ve already set out the pillars of being a good wingman — enthusiasm, an uncanny ability to network, hype, planning acumen, and simply “getting it” — which you can read in full here. But describing the perfect wingman isn’t why we’re here.
We’re here because some Washington D.C. tech guy is struggling with the fairer sex and desperately needs help. Emphasis on desperately. He’s not trying to find a ragtag crew of dudes who fancy themselves the next guys from The Hangover. No, he’s trying to find the mythical creature that is a wingwoman.
And his Craigslist listing soliciting such a person is quite possibly the most uncomfortable thing in existence and worthy of a full breakdown. Let’s dig in. All original text in quotes below.
What: Be my wingwoman
When: Weekends and weekday evenings when we’re both available
Where: Arlington VA (and downtown DC if its convenient). PUBLIC places ONLY. NOT at my apartment. NOT anywhere else private.
Why: Because I’m shy and want to meet women who are not shy
Pay: $30 per hour
I have to admit, I respect this guy’s transparency. He’s admitting to being shy and he’s trying to eliminate the creep factor from the equation by saying this won’t entail anything in the confines of his apartment. Do I believe him one second? Absolutely not, and that’s solely because I think that he thinks there’s a chance he’ll fall in love with this woman who he’s planning on paying to be his friend. A unique move, to say the least.
And $30 per hour? So that pretty much covers craft cocktails in the Arlington/D.C. area, no? I’ve never been to Georgetown (although I’d think I’d absolutely thrive there), but you’d have to imagine craft cocktails ain’t cheap. We’re talking liquid smoke and artisanal bitters in those things.
— Help me meet new people and build social networks
— Teach me some new things
— Show me new perspectives and approaches to meeting women
— Help with approaches
— Provide coaching support – help me increase skills/awareness
— Help me learn to be more interesting in a group setting, especially bars and clubs
— Help me learn to appear and present myself as more attractive/desirable (body language, clothes, etc…)
This guy isn’t asking for a “wingwoman” — he’s asking for a full-on life coach. This is like Hitch but he’s using a female instead of Will Smith. This is asking A LOT for $30 an hour. He’s pretty much asking to be a modern day She’s All That, morphing himself from a tech nerd into a full-blown casanova.
Help meet new people and build social networks? That’s fair. Teach him some new things? Sure, that’s what friends are for. But the rest of the list? He might as well apply to be a character on the now-defunct VH1 show The Pickup Artist. You can’t teach talent, and pretty much every single objective he listed is heavily reliant on talent rather than coaching.
But this is where things get aggressive.
Who you will be working with
To give you an idea of what you will be working with, I’ll describe where I’m at currently:
Look about 28 years old but I’m actually in my thirties. Am 5’8″, caucasian, with a lean, athletic build. Have a dog. I live in an apartment in Clarendon Station walking distance to a bunch of night life such as Don Tito and Clarendon Ballroom. I own a company that employs 8 people and I also make a 6 figure salary as a software developer. (side-note: If you’re interested in being an entrepreneur, I’d love to help out). I’m not an arrogant douche-bag about my career success, the reason I mention it here is because its an asset that we might choose to leverage in some way.
Okay, call me crazy, but doesn’t this guy kind of sound like a catch? I’m not one to assess how desirable dudes are, but I’m also not opposed to doing it either. I’m in my thirties but I look like I’m in my 40s. Sure, 5’8″ isn’t ideal but it’s not like he’s 5’6″. Two inches makes a huge difference. Sure, he’s not going to be The Bachelor anytime soon but this is something we can work with. Mix in a dog and an athletic build? How is this guy striking out? Is it because he’s going to bars rather than dog parks? Is this purely a strategy thing?
Because he’s willing to pay his wingwoman, we probably could’ve guessed that he made a decent salary. I never dreamt that it would be six figs though. I wouldn’t blame you for clicking directly out of this article to head straight to Craigslist to get on this guy’s radar. This is more like a résumé than it is a plea for help at this point.
I feel very comfortable when out on 1-on-1 dates with women, especially conversation over dinner, this type of interaction often goes really well. I’m intuitive and high-empathy. I tune into people’s emotions, genuinely engage, and am genuinely caring. On the occasions that I have been on dates with highly attractive women, they’ve often been “in” to me. The difficult part for me is getting the dates in the first place. This is because for a very long time I worked way too much on my company and made very little effort to be social. Most of my really close friends are people I know from high school and college before I started over-focusing on my career.
Ah, and there we have it. Emotions? Engagement? Caring? We’ve seen this before. A topic we’ve covered extensively as of late. He’s a Friend Zone Guy. Comes in too hot, too early. His issue isn’t getting the girls to go on dates — it’s scaring them off the second they sit down for some bellinis to shoot the shit and see if they mesh. Classic entrepreneur mentality.
We’ve seen this a million times before — you’re getting up there in age, you’re single, and you start to overthink. You make knee-jerk decisions that come off as too aggressive and you don’t have anyone around to tell you that you’re going to too hard in the paint. We’ll get you there, bud.
Bars and clubs are challenging for me, so I’m really hoping you can help me out here in short term and help me hone my skills in the long term. I sometimes get social anxiety in groups, this means I sometimes get uncomfortable and stressed out around large groups of people. If I am with one or two people who I am comfortable with, this doesn’t happen though… actually maybe this is normal for most people, lol
And there’s the straw that broke the camel’s back. The reason this six-figure dog-owner D.C. tech mogul is still single.
He uses “lol.” This is going to be difficult to rebound from, but we can rebuild.
At this point, if you aren’t getting social anxiety while you’re out, you’re in the minority. Anxiety is the hotness in 2018. We’ve all gotten accustomed to being on our phones because we’re just in one huge Black Mirror episode, so when it’s time to turn on the charm and get down to the nitty-gritty, our brains just shut down. It’s easy to hover over a phone and fire off texts, but it’s a little more difficult when you’re looking Maddie in the eyes with your hand trembling nearly spilling your vodka-soda.
I’m a very warm person. In relationships I’m especially warm. I also tune into and engage with my partner’s needs. For example, in my last relationship, I trained the dogs to enthusiastically greet my girlfriend when she got home from work so every time she entered the house after a stressful day, she’d come home to a bunch of positive energy. The reason I mention this here is because it helps to illustrate one of the goals here. Someone with my personality is usually not the first person a woman will choose to hook up with because there are are always 10 other taller, louder, flashier guys dominating all the attention. The trick here will be to subtly get a spotlight on me, focus some attention, give the impression of high status, get my foot in the door. Once my foot is in the door, I can take it from there.
For being a self-proclaimed “tech nerd,” this guy clearly doesn’t properly use the resources at his disposal. I’m pretty sure Hinge started in D.C. If you aren’t on Bumble, you’re not trying. Tinder works if you’re desperate, I’m told.
He needs to re-think his approach and use his comfort zone to his advantage. If you can make $100K+ using tech, you can manufacture some dates out of it too. Sure, you probably don’t need to train your dogs to properly greet your future girlfriend. That’s probably laying it on a little too thick. But at least realize that your perfect
wingman wingwoman could be your jailbroken iPhone X. Because we know this guy has a jailbroken iPhone X.
He then launches into some FAQs, because you can take the guy out of the tech world but you can’t take the tech world out of the guy.
(Q) Is this really just some scheme to come at me sideways and try to sleep with me?
(A) A fair question, but the answer is: NO. Its also important to note here that we will always meet in places that are very public.
Yeah, okay, buddy. We know what you’re doing.
(Q) Whats wrong with you? Why do you need a Wingwoman?
(A) LOL Ouch!!! There isn’t anything glaringly wrong with me. In fact, when compared to the average Joe, I’m more successful on the female front than average. I’m fairly attractive, compassionate, considerate, and genuine. That being said, I’m not good at meeting women in at bars and clubs. I tend to clam up in groups of people and randomly hitting on women makes me very uncomfortable. This is normal for most high-empathy guys. Life is a school though and hopefully with your help, we can make some improvements.
Okay, we really need you to stop using “lol.” This could explain why he’s abandoned dating apps and is resorting exclusively to bars. It’s entirely possible that he has Big Bang listed as one of his favorite television shows. Stay tuned.
(Q) Why do you want a Wingwoman?
(A) Good question! I don’t have any friends that like to go out; and like the average person, I get pretty uncomfortable when I’m all alone in large crowds of people who I don’t know. Additionally, this is an excellent way to get out of the “dating rat race” so to speak. Instead of being some creepy loner who goes around hitting on people and making them uncomfortable, instead we can have positive interactions with lots of people and build some genuine, lasting friendships. I’m sure there will be lots of fun along the way, but I’m hoping that eventually we can find me a life-long relationship.
Honest question here: is it better to be a creepy loner who randomly hits on people, or is it better to be a creepy loner who pays a girl to hang out with him so he can do it? I know all your friends are taken, but maybe we need to change our perspective here.
(Q) What kind of women do you like?
(A) Confident. Outgoing. Positive. Active. Ambitious. Emotionally healthy. Happy.
So a normal person. Got it.
(Q) No, I mean “looks-wise”, what kind of women do you like?
(A) Obviously attractive women. Don’t care about race, hair color, height, body type or anything like that. I do have what I believe is a “pheromone” bias towards latin women. What I mean by this is that their natural body smell is more likely to turn me on. If you’ve ever thought someone smelled so good that you liked to breath in their breath as they breathed out, then you know what I’m talking about. Anecdotally, I get the impression that this is something that only a minority of people ever experience.
Uhhhhhhhh, what? Okay, I feel like I was being pretty positive with his chances to find love here and then he has to go on some tangent that latin women smell better than every other race but he’s one of the select few to realize it. Goddammit, man. We were doing so good. You can’t use phrases like “body smell is more likely to turn me on.” This is situational awareness that you’re lacking. Fucking hell.
(Q) Are you looking for something long-term or short-term?
(A) Long term. The reason I am putting this much effort into this endeavor is that I want to find something truly incredible for the long term. How does this affect what we will be doing? We won’t be going for the “easy win.” That being said, its going to take a long time to achieve this, and the road is likely to be paved in lots of short term, less serious relationships, hookups, one night stands, etc…
A major flaw of modern dating is that too many guys are reeking of desperation while trying to find a long term relationship. I’m not going to tell you that you need to play it cool or anything. You want what you want. But at least go in with a “let’s see how this pans out” mentality rather than trying to marry the girl night one. You’re risking it all here, and that’s not a good thing.
(Q) How does the pay work?
(A) Half up front at the beginning of the night. Other half at the end of the night.
No. You need to Venmo them up front. Sure, they may disappear in the bathroom, but this gives off a weird vibe like you’re going to kidnap them.
(A) Weekends and some week days when we’re both available. (no strict schedule)
That’s nice of you to be accommodating. I’m not realizing that you’re just 100% hoping to date your “wingwoman” rather than actually use her as a “wingwoman.”
Pay is $30 per hour.
How to apply
Respond to this post with a little bit about yourself, why you are interested in the position, any questions you have, and/or any ideas you have.
Looking forward to working with you!
If you’re part of our Washington D.C. readership, look no further. I’d say it’s better than being an Uber driver, but honestly, I’m not sold yet. At least you’ll get to play with his dog..