The Art of Being a Wingman

Congratulations, you have mastered the art of courtship and are now in a relationship with a female! The only problem is that your buddy is still single and it pains you to see him struggle with the basics of courtship even after reading “The Art of Courtship” (See post on July 29, 2014). Since you are a good friend, and because you can’t bear to hear him say, “Baby, I’m so hot, you can’t help but play it cool,” one more time, you decide to become his wingman.

Having successfully navigated the waters of courtship yourself, you are probably confident, even arrogant, with regards to your courtship skills. You probably think that being a wingman will be easy because all you have to do is find your friend a suitable female and then nudge them down the road of courtship. Sure, igniting the fire of romance is certainly a large duty for any wingman. However, what most wingmen forget is that the whole reason why your friend needs you is because he doesn’t have the necessary skills to succeed at courtship. In most cases there are messes from the past that you will need to clean up before you can move forward, and oftentimes a wingman needs to stoke the fire throughout the early stages of the relationship.

Let’s start from the beginning with some scenarios you could run into. So, suppose your friend has just made another mess at the local malt shop. In your conceit, you are tempted to bring him right back. At this point though, you have to remember that your friend is not emotionally stable. What he really needs are some kind words such as, “Dude, you did your job. You brought the court, unfortunately she was unable to bring the ship to port.” Then give him a few days to collect his thoughts.

Another situation you could run into is perhaps your friend has “come on too strong” with a female. Maybe he saw a female at the malt shop and was so smitten that he mistook her completely ignoring him as “playing it cool.” As a result he found her address online, broke into her house, and played the cello as she walked in. At this point, your friend has breaking and entering charges as well as a restraining order on his hands. With this in mind, it is paramount that every wingman be well versed in law so that he can help his friend out in a jam like this.

A final situation that you could run into is maybe your friend has the basics of courtship down, but still lacks some of the more advanced skills. For example, maybe your friend has succeeded at the malt shop and successfully invited a female over for dinner. At this point he decides to make his famous mustard hotdish (a layer of tater-tots on the bottom, a two inch layer of mustard, ground beef, and chopped onions). This is where the wingman needs to step in and put his culinary skills on display. (I suggest freshly caught grouper and huckleberry pie.)

Now that we have gone over a few general situations, I would like to go more into the specifics. As I mentioned before, most wingmen are arrogant thanks to their own success in the realm of courtship.  A wingman with a brash attitude is usually clueless though. In fact, most supercilious wingmen walk into the malt shop, go up to the first female they see and say something like, “See that male over there. He said something about courtship and having a difficult time. Then he told me that he would buy me a malt if I came with him and got the ball rolling. So, it might be a good idea if you go over there and talk with him. If it works or it doesn’t, either way my feelings won’t be hurt. To be honest, I am just here for the free malt.” In some extraordinary situations, having a wingman this inept has elicited the pity of a female and actually led to successful courtship. To become an elite wingman though, one will want to use the following plan of attack.

First, as you walk into the malt shop (which is usually a good place to start unless you want to aim for the extreme ends of the spectrum, a risky endeavor for any man) you need to turn your focus from malts to finding a female for your friend. As I have mentioned, you will no doubt feel tempted to waltz in and approach the first female you see. A better method though is to sit down, “play it cool” for a while, and just get a feel for the malt shop scene. (It should be noted that, if done right, “playing it cool” can sometimes lead to females approaching you and your friend. However, this is a rare, acquired skill that should not be relied upon.)

Once you have a feel for the vibe of the malt shop, approach a female and break the ice by bringing up a current event. For example, you could say something like, “What are your thoughts on the French ambassador to Canada’s speech last night?” Even if she didn’t hear the speech, she will be flattered that you have fancied her an intelligent woman. At this point, you can start to work the magic by saying, “I noticed that your left ring finger is conspicuously devoid of jewelry. Do you anticipate this to continue in the near future?” Her answer to this question should let you know if you should abort or proceed to sealing the deal. 

If you need to abort, you didn’t correctly asses the vibe of the malt shop. So, before approaching another female, sit down with your friend for a while, “play it cool,” and reassess the malt shop flow. Once you have your finger firmly on the pulse of the malt shop, take it from the top, and follow the blueprint in the previous paragraph.

On the other hand, if your assessment of the malt shop was solid, and you are ready to seal the deal, proceed by saying one of the following (1) “See my buddy over there. He’s pretty sweet on you,” (2) “See that chap over there. He is rather smitten by you,” or (3) “See that fellow over there. He is interested in endeavoring down the road of courtship with you.” (Make sure to instruct your friend to nod his head back slightly when you and the female look his way.) As to which of these to use, I suggest going with your gut. If you truly have your finger on the pulse of the malt shop, you will know which is best.

At this point the female will sit down with your friend. If you have correctly prepared him, he will have a strong knowledge of the French ambassador to Canada’s speech (or whatever current event you chose) and be able to seamlessly take your place in the conversation. With the conversation rolling, you will want to give your friend some space. So, go and enjoy a malt at a table by yourself.

If your friend has followed your instructions correctly, he will ask the female to dinner. With a “Yes” in hand, he will give you the signal (I suggest something subtle like having your friend pat himself on the head). Once you have the signal, you will complete a perfect day at the malt shop by bringing them one malt with two straws.

With your friend solidly on the road of courtship, you can ease off the wingman throttle a little and let your friend exercise the courtship skills that you have bestowed upon him. However, be prepared to jump into action at a moment’s notice if, for example, you see your friend buying mustard in bulk.

In conclusion, when acting as a wingman, check your arrogance at the malt shop door, and remember that courting a female and helping a friend court a female are completely different. Not only that, make sure that your culinary skills are sharp, your knowledge of law stout, and in case your friend encounters a classy woman, it does not hurt to have serviceable cello skills either. And one more thing, make sure to remind your friend that it’s, “Baby, you’re so hot, I can’t help but play it cool.”