The Art of the Wingman

I’ve been watching trashy American TV since the days when Friends episodes were still being played on Channel Four, and weren’t even repeats!  And so the phrase ‘wingman’ has been in my vocabulary as long as I can remember.

However, it’s only over the past few months, as I’ve begun to attend more and more singles events, that I’ve actually begun to learn the virtue of a good wingman.  And just how bad, in general, women are at the role!

I’ve never gone to bars with the intention of picking up guys.  And so I guess that’s why I’ve never been too fussed about needing a wingwoman.  Most of my past relationships developed from friendships, and so I didn’t overtly need a third party to help showcase my assets.

But in a world of singles events and dating-related socials, the need for a decent wingman is more pronounced.

You’re meeting complete strangers, in a room full of other singletons.

For a start, with so many members of the opposite sex to trawl through, it can help to have a second pair of trained eyes.  Someone to give you a nudge in the right direction if they spot someone you might like.

And then, if you do spot someone you might like, you need to catch their eye, and keep it.

Often the best way to do that, is with the help of a friend, who has a common goal in mind.  The goal of setting YOU up with a match.  And ONLY YOU!

Which is where the Wingman issues begin.  Because at a singles event, your Wingman is also single. Which means he or she has their own needs to attend to at the same time.

The thing about adopting the role of Wingman, is that you can’t make a half-hearted effort.

It’s a joint mission.  And you have to see it through to the end.  Regardless of your own desires and needs.  Your achievement is your friend’s happiness.  Not your own.

And so like a military operation, that means communication and forward planning.

You and your friends need to understand who likes which guy or girl, and who is going to help the other person achieve their goal that evening.

To be perfectly honest, one of the reasons I think I fail so badly when it comes to selecting Wingmen or women, is by the very fact I’m not planning an attack.  I’m not tactical in my dating.  I just see dating events as fun nights out, not a serious attempt to find a boyfriend.

And so when I go on nights out,  rather than choosing the best companions to complement my personality, and help me find a nice guy, I choose my most fun, sociable single friends.

All well and good normally, but often the completely wrong approach for a singles event!

Firstly, fun and sociable can often mean loud and overpowering.

And whilst a friend who loves to be the centre of attention can be great in a number of situations, when you’re trying to chat up a guy you like is most certainly NOT one of them!  No one wants to recruit a wingman who draws more attention to his or herself than they do to you.  They’re meant to be there to help you, not cause more of a distraction or hindrance.

And secondly, I’ve never thought enough about what kind of guys me and my friends are attracted to.

Because, if you’re recruiting single friends to go to a dating event with, then the worst thing you can do is tag along with a friend who is attracted to the exact same guys or girls as you.  That person isn’t your wingman.  He or she is your competition.  And when you’re competition is your friend, it all gets far too messy.

Which is why the best wingmen are people with zero interest in the men or women you’re hoping to meet.

The obvious solution is to recruit a wingman who isn’t single.  Which works in a normal social environment, but just isn’t playing fair if you’re attending an all-single event.

Failing this, in my opinion, the best wingmen are therefore either friends of the opposite sex, or gay friends (if you’re straight).  That way you ensure you’re not going to be trying to seduce the same target.


As for How to be a Good Wingman

Well, at a singles event, once you’ve established who you are trying to set up (work on one person at a time, unless both of you like two members of the same group), the key to acing the role of wingman is to remember that you’re trying to showcase your friend, not yourself.

Think carefully before you speak.

Rather than turning conversation to your own stories, try to turn the conversation to something your friend can talk about.  Contribute to conversation, but don’t dominate it!

Know when to walk away.  

If your friend is getting on well with his or her ‘target’, and it’s just the three of you in the conversation, move away.  If there is a fourth person involved, draw them into a separate conversation, so your friend can talk one-on-one with the person he or she likes.

Take one for the team.

A crass expression, but it sums up the situation.  No, you might not be interested in the target’s friend, but be a good friend, and at least be polite and engage in conversation with them for a bit.  It’s the traditional comedic Wingman scenario – where the wingman gets stuck with an unattractive friend.  No, you don’t have to pretend to be interested in them, just be polite.  Hopefully they will be intuitive enough to know whether or not their friend wants to be left alone in conversation with your friend.

Don’t cock block.

Again a crass phrase – and it’s interesting, because I think this topic really brings out the ‘male dater’ in me, but there’s no appropriate female equivalent of this phrase (as far as I’m aware?) that sums up the scenario this well.

There is nothing more frustrating, as a singleton, than getting on well with someone, only to have your friend intervene in some way that completely ruins the magic.  Whether that’s simply interrupting the flow of conversation, dragging you away, or full on flirting with your ‘target’.

Read the situation.

Take a step back, and try to work out what your friend is doing.  If he or she looks happy, then don’t interrupt conversation.  We’re adults, most of us don’t need ‘rescuing’ from bad conversations, we can make our excuses and leave.

And if you’re really bad at reading signs, then pre-organise some code words or gestures, so that you know whether your friend is happy or not.

One of my friends uses a fake name whenever a guys she’s not interested introduces himself.  Simple, and effective (though confusing if you meet up again later in the night!)


Miss Twenty-Three xxx






5 Comments on The Art of the Wingman

  1. This is all good stuff, man. I always thought a committed girl (who is a friend) was always the best wing man for me.

  2. Men and women are quite different. In general, women are more passive about dating and just waiting for someone to approach them. Not all the time, but isn’t that what usually would work best for you girls, most natural?

    It’s us men that are so desperate and have to do so much work and strategy to find a nice girl 🙂

    Also, women seem to be more competitive with each other. When guys go out together and hope to pick someone up, there’s no much sense of that with friends. Perhaps strangers can be rivals, but not your friend. There’s plenty of fish in the sea and not much concern that we’ll fight over someone. Women can suddenly be very possessive over one guy, get jealous. Unless one is in a deep relationship, or had some crush for a long time, with men we’re pretty happy to hook up with anybody reasonably attractive and there’s no need to step over each other.

    Am I generalizing in a sexist way or am I on to something?

    Not that I’m an expert in picking up, just observations.

    All in all, a wingwoman just doesn’t seem to work and doesn’t seem necessary in the same way.

    • Hmm, whilst I don’t disagree that as a girl it’s preferable to have a guy approach you, I think the female wingman approach is more subtle. Making you stand out in amongst the crowd, so that guys do approach you. From a female perspective, I know a lot of girls who inadvertently act like a negative wingman – they actually distract the guy you want to be talking to, without realising. I think with girls, rather than understanding how to promote your friends, sometimes it’s simply a matter of understanding when to leave someone to it,

      Thanks for your comment Ray 🙂 xxx

  3. I would have thought that women would be more attuned to being “wingmen”.
    I just imagined that girls would always be out for the best interest of their friends.

    Perhaps the concept of a wingman is a bit alien to most girls since as Ray H kind of alludes to – that women rarely have to employ the same approach methods as men.
    Perhaps this is just how this and most western societies work – women preen and present themselves sometimes overtly and it’s up to men to do the chasing. However I will say Kudos to those women / girls who decide to take matters into their own hands.

    Having played the role of wingman many-a-time I also agree that you are there to showcase your friend however it’s not supposed to be a serf and master pairing. It’s a team of two, a co-operative, a collaboration.
    You support each other and bring out the best in each other; sometimes exaggerating the best qualities of each other so as to make each team member seem more appealing to their target. Throwing in a bit of self deprecation and gentle mocking so as not to come over as completely conceited and false.

    Normally a team of two would never engage a party / group larger than theirs unless the goal is for one person to distract potential “cock-blocks” (multiple friends of the target) whilst your partner talks to the target.
    In such scenarios you would have to be super confident (which is where a super confident friend might come in handy) since you would be taking on the attention of a large group of strangers and keeping them entertained or distracted for long enough that your partner can build rapport with or separate the target from the main group. However you would obviously have to make clear which one was your target so that the wingman (aka friend) would make sure not to engage them in the distraction whilst you simultaneously engage the actual target so as not to give him or her time to work out what was happening.

    This is where PUA training for me at least comes in handy because as a socially inept person I would have no ice breakers unless I had planned some in advance. It’s actually a useful skill-set in a social setting for people who are not confident (guys and girls!) at least until you start reading and discussing broad topics and having an opinion on anything so that you can actually hold a conversation with strangers.

    Anyway, I feel that ultimately the best type of wingman is simply a friend who also wants to meet someone, who you know quite well and can have a good time with even if the target is not acquired.

    PS: I wonder if the term wingman as a person to pick-up girls with originated from Top Gun …

  4. I think you’re probably right about Top Gun. I think often girls don’t even realise they’re being a distraction – unlike boys, who’ve grown up with a wingman-approach to pulling girls, girls are so used to sitting back and attracting guys that often they can’t see how damaging their actions are to another girl. Whilst you normally assume girls are more perceptive, in my experience of going out on nights out with both guys and girls, I think girls often act a lot more selfish on nights out, particularly at singles events! xxx

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