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Published September 06, 2012

My friends, the sacred art of wingmanning is dying. This vital player in the pursuit of romance is an endangered species in the jungle of love. The skyrocketing divorce rate, the internet dating boom, the sub-prime mortgage disaster. All these things can be blamed on the decline of the modern wingman (In all fairness, the mortgage crisis is a stretch, but there’s so much blame to spread around, it’s gotta land somewhere. It’s like KY Jelly.) Do not fear, however, for I am here to revive this lost art. Let's start with some frequently asked questions.

What is a wingman?

A wingman is a person of the same gender who aids you in your quest for romance. There’s no such thing as a wingman of the opposite gender. You’ll just end up falling in love. Have you never seen a romantic comedy?

Why do we need them?

Because starting conversations with random strangers is just plain awkward, especially if you are picturing that person naked in your mind. The presence of a wingman tells the girl or guy you’re trying to woo that there’s at least one other person on Earth who can stand you. Which is one more than he or she thought there was before.

What does a wingman do?

The specific functions of a wingman will be covered a bit later, but in general they help break the ice, keep the conversation going, make sound decisions when you’re unable (read: drunk), and pull the ripcord when necessary. They perform these tasks in the hope of providing you with a wonderful evening, full of fun and phone numbers. And all this service might cost you is a late-night burrito.

In what situations is a wingman valuable?

The short answer is every situation. Applying for a bank loan, sweating a performance review at work, or doing hard labor in a Siberian work camp. There are few situations in life where having a buddy to ease your nerves and throw in a few jokes isn't helpful. However, for the purposes of this column, we’ll stick to situations where you're out, at a party, in a bar, or on a date. These are a wingman’s bread and butter (Although if your wingman is fat, their bread and butter might actually be bread and butter. Keep that in mind.)

There are three basic situations that you and your wingman may encounter. For the purposes of the article, the subject and wingman will be male, and their pursuits will be female. Ladies please don’t be offended. Reverse the scenarios and the advice is still solid.

2-on-1 Two guys, one girl

2-on-2 Two guys, two girls

2-on-many Two guys, any number of girls in a single group. The number of girls must be: A) greater than two and B) an integer. I know what you’re saying. I’m discriminating against midgets and dwarves by excluding decimals and fractions. But in truth, you’re the bigot. I count them as whole people, dick.

Most of the following rules apply to all the above situations. Any exceptions will be clearly outlined, so please continue reading with the knowledge that afterwards, you will be fully equipped to perform any and all wingman duties should you be called into service. Good luck.

Rule #1 It’s not about you

This is the mantra of any good wingman. You have to approach each situation thinking not of yourself, but of your buddy. Let’s be very clear: two men cannot wingman each other (at least not in the lower 48.) The roles need to be clearly defined, or you’ll just end up competing with each other. It is possible for both of you to play the role of wingman in an evening of barhopping, but you must trade off. So if you choose to be the wingman, your romantic needs are on hold.

Rule #2 Always have a game plan

This should happen during pre-game at the house, cab ride to the bar, or over the evening’s first drinks. Find out what the goals are for the evening because this will affect your approach. If you’re buddy wants to meet a nice girl, get her phone number, and begin the long walk down the aisle, then you should plan accordingly (or burn him with matches. It's up to you.) You’ll steer him away from drunk girls who slam the bar with their hand after shots, have excessively raspy voices, yell for no reason, or wear skirts/dresses so short you’d definitely see more than you bargained for if you bent over to tie your shoe. If on the other hand, he wants to make out in a bar with a stranger, lead him directly toward those girls, and grab a bar stool that’s a safe but reachable distance away.  During this planning session, you should learn his preferences. Tall, short, blonde, brunette, redhead, college-educated, GED, etc. (If 'redhead' is listed among his preferences, make sure you have on shoes in which you could run at least 1 mile. Don’t ask questions. I pray you don’t have to find out why.) Next, you need to find out his weaknesses. This will point to the areas where you can be of greatest service in the night to come. Lastly, and most importantly, have a safety word. This should be a word not hard to slip into casual conversation that will signal the need to leave immediately. As you become more practiced as a wingman, you will learn to spot disaster before it happens. The safety word is a priceless tool should you realize the woman your buddy is talking to is: A) a man, B) Bat shit insane, or C) a prostitute. Don’t laugh. It happens more than you think. For the hearing impaired, any sign other than thumbs down, holding of the nose, or the middle finger will serve as an adequate safe word and let your wingman know it's time to leave without alerting the women nearby to your displeasure with them.

Rule #3 Introductions are everything

The role wingmen are most often asked to fill is ice breaker. As mentioned before, it’s extremely hard to introduce yourself, start and maintain a conversation, date, marry, and divorce a total stranger all on your own. That’s why it’s always best for the wingman to make an introduction.

You don’t have to come on strong. There’s no need for a line, and there’s no need to offer to buy a drink. Women have noses for game like bloodhounds.  Those approaches are tired and played out. Just introduce yourself, shake hands, clink glasses, and introduce your buddy. That’s it. Either they’ll engage you in conversation and drinking or they’ll throw your shit into the fourth row like Dikembe Mutombo in his prime (There are women who literally will wag a finger in the face of would-be suitors with weak game.) Since most women are conflict adverse, the former will happen far more than the latter. And even if they’re just being polite and aren’t interested, the longer you can talk without being sleezy or overbearing, the more interested they’ll become.

*Exceptions: In a 2-on-1 situation, your buddy needs to introduce himself. The handoff is not an easy move to pull off and should not be attempted by a novice. In a 2-on-many situation, seek out the most friendly-looking girl. This will facilitate meeting the entire group. In any given group of girls there are certain roles to be filled. First is the queen bee. She's pretty, but not interested in you. Next is the mother hen. She's decent looking, but constantly worried about each and every member of the group. And finally there's the Calvin Klein. She's a friendly girl who just wants to show you her underwear. When wingmanning, avoid the first two at all costs, and aim for Calvin.

Rule #4 Dead Air = Dead Meat

Think of yourself as the coal shoveler on a train. When the conversation starts to lose steam, you stoke the fire. This doesn’t mean you’re dominating, it just means you’re there to interject with a joke, compliment, or change of subject when necessary. Steer the conversation towards your buddy’s strengths. Possible areas of strength include: working in any capacity with children (including juvenile detention guard), old people, or animals. Also, having a nice car, enormous house, or a helicopter are great topics of conversation, but when brought up, your buddy MUST be bashful about them. Otherwise he’s just a douche. Keep him away from divisive or rant-inspiring subjects. Any topic that would get 20 minutes of airtime on Fox News should be avoided like nachos at a Dodger game.

*Exceptions: In a 2-on-1 situation, once you’ve gotten the conversation going, you’re a ghost. Don’t leave the bar, but get outside of visual range. Cell phones are key here. Be prepared to receive a text should your buddy leave with the girl, or need a Sky-Hook style rescue.

Rule #5 Always Be Selling

In a great sales pitch, very few of the words are encouraging the customer to buy. Instead, the salesman gets to know his customer, talks about things they have in common, finds out what the customer is looking for, and simply gets them to say the word 'yes.' They don’t have to say yes to buying, they just have to say yes to something. The same is true for wingmen. Every word out of your mouth doesn’t have to talk your buddy up. You just have to talk enough to find out what she wants, her gameplan. Then convince her that your buddy is what she’s looking for. She doesn’t have to say “Yes” to liking him, loving him, or wanting to have his children. She just has to say yes to something. Another drink? Another bar? Food? All of these questions ask simply, “Wanna spend more time in the company of my friend?” A yes to any one of these, and you’re golden. She’s not necessarily going home with him, but he’s getting her phone number. As the wingman, you don’t always have to be the one to ask these questions, but you must make sure they get asked.

Rule #6 Be Unavailable

One of the most common pitfalls of wingmanning is attracting women inadvertently. That’s why it’s important to get it out of there upfront that you’re unavailable. If you’re married, have a girlfriend, or a communicable disease, that’s great. If not, make something up. Anything is fine as long as it get’s you off the market and puts your buddy in the spotlight. A woman looking to meet someone will shut down like the DMV at 5 pm when she finds out you’re taken, so quickly show her your single friend, so she doesn’t run away. Don’t make your reason for unavailability weird or off-putting. This will just cause them flee, and your wingmanning adventure will be over before it started. Just keep it simple.

*Exceptions: In the 2-on-2 situation, it is permissible to flirt with the girl your buddy isn’t after, so long as your witty banter doesn’t affect your wingmanning duties. In the 2-on-many situation, you may often find that you attract a girl yourself, just through excellent wingmanship. Again, this is allowed as long as this pursuit doesn’t distract from your primary goal.

Rule #7 Know when to pull the rip cord

This rule applies to conversations and to evenings as a whole. If you sense a conversation isn’t going well and the girl(s) aren’t feeling it, don’t be afraid to move on. Not everyone is gonna like you or your buddy. Meet as many women as you can in a given night. And when that night is over, shut it down. If you’re buddy is too drunk to stand, speak intelligently, or order his burrito, it’s time to go home. Going home empty handed is not a loss; it’s the sign of a truly great wingman. There will always be another night, so scarf some food, tell some jokes, and get some sleep.

The wingman experience, if done right, should be almost as enjoyable as being wingmanned yourself. If you’re married, have a girlfriend, or have resigned yourself to living with multiple cats, wingmanning might be the highlight of your week. Stick to these rules, and you’ll never go wrong. Remember, free burritos are delicious.

 

 

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