10 Surprising Rules on How to Be a Wingman

how to be a wingmanUnless you exclusively meet women by yourself, sooner or later you're going to have a buddy along with you when you meet a new girl or two. And what your buddy does -- and what you do -- can go a long way toward determining the outcome of that encounter.

There are, it seems, as many prescriptions out there on how to be a wingman as there are on how to become a millionaire, or how to get six-pack abs. But, you know me -- I don't tend to agree with too much of the advice that's out there. I usually find it overcomplicated and too "fancy."

Like, if you want great abs, you don't get the Super Ab Roller 3000 and start rubbing lotions on your stomach to melt away the fat. Instead, you just scale down the number of calories you're taking in and cut your carbs to drop the belly that's hiding your abs, and regularly hit the gym, go grab a bar above your head, and start lifting your knees up against your chest until your abs are on fire a couple times a week to build up your abdominals. Presto, great abs without magic machines or mysterious ointments.

Learning how to be a wingman is like that. You'll get all kinds of crazy advice out there -- some of which I'll highlight today, as examples of what not to do, before we get into what to do. But you'll be better off avoiding all that crazy advice, and instead sticking to what works.


Wingman Tips You Can Safely Ignore

I'm not sure why it is, but winging seems to be one of those areas in doing better with women that's particularly replete with detrimental advice. I suppose if a guy's out with another guy who's good with women, and he does something silly but he sees his buddy succeeding in spite of what he did, he may be liable to think whatever it was he was doing worked -- even if what he was doing was wrong.

That's my current theory on where all the shoddy advice comes from, anyway. Regardless, there's a lot of bad information out there that does a great job of making the guys doing it look pretty silly -- and looking silly and being sexy, as you need to be if you want consistent results with women, aren't exactly closely related.

Let's highlight a few pieces of not-so-great advice that are floating around out there just so you know it when you hear it.

Bad Piece of Advice #1: Enter the conversation no later than 2 minutes after your buddy's met new people.

I guess if guys are really new and they need a lot of help just maintaining a conversation, this is okay... if they're really honestly just starting out and can't engage two women at once and win them over without a buddy taking on one of those girls, and they really just need to build up some very basic experience. For everyone else though, this is awful advice.

What you end up seeing is two guys walking up to talk to two girls together, or one guy starts talking to two girls and his buddy jumps in on his own 30 seconds or a minute later.

Why's this bad? Think about it like this. You're out, minding your business, when suddenly a stranger walks up and starts talking to you. Okay, mildly alarming, but he sounds cool, it's okay. You gauge him and assess where he's at.

Now let's say while you're still just getting comfortable with this new guy's presence, another guy walks up and starts talking to you. Now you're really starting to feel a little uncomfortable... even if these guys seem cool, and not creepy, you're probably going to want to make a swift exit.

This is what happens when guys ambush girls like this -- the girls get startled and uncomfortable and make a fast exit. Even if they don't leave, they're often too off-balance to bother getting all that attracted.

Bad Piece of Advice #2: Both guys have to make friends with both girls.

All right, this one's good in theory, but bad as applied by most guys out there meeting and getting to know new women. What you usually end up seeing is guys trading girls back and forth, exchanging light, shallow conversation, in an effort to make sure both girls approve of both guys.

What ends up happening though, is that both girls end up confused about which guy is going for what girl -- or even assuming that the guys are just out to be social and not really looking to move things forward with them. Hence, they put their own emotions on hold -- and attraction dries up quickly.

Bad Piece of Advice #3: Guys should "take over" new groups they join.

As mentioned in the post on how to be an alpha male, trying to out-alpha the people already in a group, in order to show to your new friends how powerful and attractive you are, pretty much universally comes off as tryhard.

Not only that, but when you and your pal are doing it together, most groups of people -- unless the both of you are extremely cool, extraordinarily engaging individuals -- end up looking at each other, collectively wondering to themselves, "Who the hell are these guys, and how did they invade our group?" and then end up re-forming their circle again somewhere else (usually adjacent to where they were)... without you.

Each of those three pieces of advice -- enter the conversation no greater than 2 minutes into it, both guys make friends with both girls, and guys should take over the groups they enter -- they're all pretty common advice... but they're all based on a very superficial understanding of group dynamics, and the way those pieces end up getting applied by most men is pretty detrimental to those men's own success with women.

That said, let's get you some more solid stuff to work with.

how to be a wingman


How to Be a Wingman -- 10 Surprising Rules

What if I told you that the most important rule of being a good wingman was in not stealing your buddy's thunder? And what if I told you the second most important rule was allowing time for girls to get comfortable with your pal before you jump in?

Well, in fact, those are the first and second most important rules. And there are a lot more where those came from. I call these rules "surprising" because most of them are going to go against the grain of what you've probably heard elsewhere.

But I think you'll like 'em anyway.

  1. Don't Steal Your Pal's Thunder. When I first started meeting women with wingmen (I worked on meeting girls for a year and a half solo before ever rolling out with a buddy), I was both stunned and annoyed at how consistently other guys I'd roll with would come in a lot higher energy than me, take center stage, and then crash and burn and cost both of us our girls. I eventually figured out how to deal with situations like that, and I'm the better for having learned to do so, but it was poor wingmanship by my pals when we started out.

    It's vital that you don't steal your buddy's thunder. Having met a pretty large number of groups of people throughout my career as a social artist, I've picked up a thing or two about how groups respond to that kind of thing, and what I've noticed is groups tend to treat the guy who opens them as the de facto "leader" of his group, and that any attempt by his wingman to take center stage or in any way tease or rib his friend a little too hard gets viewed as dissension among the ranks, and you both get viewed as lesser men.

    If you want to maintain the respect of the people in the groups you meet, letting the guy who opened maintain the "lead" role in the interaction is a crucial part of how to be a wingman.

  2. Give Girls Time to Get Comfortable Before Joining In. Contrary to the whole "jump in before 2 minutes" philosophy, I'm a believer in the "chill on the outside as long as it takes for your buddy to get the girls warmed up to you" school of thought.

    Think of it like this: if two men are pursuing two girls, those girls are going to feel a lot more pressured and a lot less comfortable than if one man is pursuing them, and one is minding his own business five or ten feet away.

    When you let your buddy get the girls comfortable while you keep a low profile (or when he lets you get them comfortable while he stays out of the picture), you give them time to get used to the presence of this new man, without their attention being split and disoriented by two new men. I've seen it done both ways a number of times and trust me, it works better when one guy wins them over -- not two.

  3. Resist the Urge to Oversell Your Wingman. There's some old advice floating around that you ought to talk about what an amazing guy your friend is. Don't listen to it.

    Trying to beef up your friend's credentials comes across the same way to women as does trying to beef up your own credentials. Women aren't fools; they know that the buddy you're bringing in is there to help your odds with them. And they know that anything you say about him is to do so, too. Building him up has the same effect as talking about your own value; it comes across like you're trying to showboat, and it comes across as chasing.

    There's another strike against it, too: when you start talking about your pal before they've met him, and then you build him up to them, and then he shows up, it all ends up sounding rather... "planned out."

    And women hate feeling like any part of an interaction was logically, carefully "planned out." They want everything to feel natural, spur-of-the-moment, and they want to feel like this isn't something you do with every girl... just them. Most people don't mention their friends until their friends have entered the picture; I'd recommend you do the same.

  4. Bring Your Buddy In When Both Girls Are Warm. If you're the one who's opened, it's your responsibility to bring your wingman in -- not his responsibility to jump in. If you're already on the inside, he shouldn't need to go open the girls himself and carve his way in -- that's poor wingmanship on your part.

    This is one of the biggest mistakes I see guys making: one guy walks up and starts talking to girls, and the other guy kind of hovers around them for a minute or two, then goes up on his own and opens a girl on his own or introduces himself. This ends up coming across to the girls like two strangers walking up to meet them -- not like one stranger (the first of you), and one friend-of-a-friend (the second of you, if he's properly introduced).

    Again, it also lends itself to feeling quite planned out and calculated if one friend goes in first, the other hovers around, and then he goes in too, unless the guy on the outside does it really smooth. Cut the necessity for good acting chops out and just have the man on the inside welcome in the man on the outside. Sometimes the girls will ask for this, too ("Why's your friend standing over there?"), which makes it even easier (you can invite him over and set a chase frame by saying, "These girls were asking for you, brother!").

  5. Address Your Friend Rather Than the Girls. This is another big one that most guys get wrong. Most guys say, "Ladies, I'd like you to meet..." as if the women are the ones who need to be impressed by your friend.

    Instead, you're going to say, "George, I'd like you to meet these two lovely young ladies I've just gotten to know..." because it isn't the girls you're trying to impress. It's your friend you're trying to impress... with the girls. That's what's communicated to them at the outset, and they automatically feel he's more important; and your friend gets this feeling too -- it's almost like you've already placed a chase frame on the girls and they're now pursuing your buddy from the very beginning.

  6. Give Your Buddy a Proper Introduction. This doesn't mean build him up, but it does mean you give both him and the girls you're introducing him to things to start talking about right away.

    So, you might start by saying:

    "Christie here's a nurse who works over at Mainline Hospital. She paints pictures of landscapes and wants to run away to Thailand to go live for a year sooner or later, and not tell anyone.

    Christie, my buddy Zach's been a painter since he was finger-painting at 3 years old, but his paintings today look a little better than that. He was just in Thailand a few years ago; he can probably even give you some recommendations."
    Give them both commonalities wherever possible (as in the example above), and do your best to make those commonalities in areas where your friend comes across as more experienced than the girl. I won't go into why in this post, but women tend to be more attracted to men who are more experienced than them in the things they're interested in than they are to men who are less experienced or ignorant of those things.

    Having stuff to riff off of means your buddy and his girl jump instantly into solid conversation and skip the awkward getting-to-know-you fumbling in the dark trying to reach the hook point. It's one of the best things you can do for a wingman of yours.

  7. Stay Paired Up. There's nothing worse than one wingman dropping the conversation with his girl to be social and get to know the other girl and talk with his friend a little. Because, what happens is, now his girl is out in limbo, with no one talking to her, slipping closer and closer to auto-rejection each passing second, while he disrupts his pal's conversation and potentially even ruins it.

    If your girl likes you, and your buddy's girl likes him, trust that there's no need for you to "be social" and win over the other girl. She's going to be so thrilled that she found a guy and her girlfriend is happy too that she isn't going to sacrifice what she wants to stop her friend from having what she wants. It just doesn't happen.

    Note: if there are more than two girls (e.g., if you and your wingman are talking to a group of three girls), generally speaking, the more experienced / socially adept of the two of you should take two of the girls and let the other focus on one. Having the more adept of the two of you handle both girls makes it more likely the girls stick around and there's a good outcome for both of you.

  8. Move Together. Just like moving girls within a few minutes is critically important when you're on your own, it's just as necessary when you're winging a friend. Within 10 minutes or so of meeting girls with your wingman, look for ways to move them. See if you can get them to join you for a coffee, an ice cream, or a water, or at least move them to another part of the venue. Moving them gets commitment and buy-in, and you vastly up your odds of accomplishing something with women later on in the day or night when you move them early on first.

  9. Extract Together. It's usually good practice to pull your girls together. Both of them will be more comfortable that way. Try and sort your logistics out before going out with a friend -- will you go to his place or yours? When you go for the pull, there are two techniques you can employ:

    A) Address your girl first. If your girl is very much into you, whisper to her that the four of you should get a nightcap or go hang out together or go to an after party. Once she's agreed, announce it to the group, and she'll likely chime in in support of the idea, making it more likely her friend agrees too.

    B) Address the group first. If your girl is less into you, and your buddy's girl is more into him, address the group (and, more specifically, your pal's girl). "What say we all go chill and have a few quiet drinks to end the night?" you can ask, spending most of your time looking at her as you do so. Because she likes your friend, she's likely to support the idea, and may very well encourage your girl to come along even if she was previously reluctant.

  10. Get Alone. Once the four of you have arrived somewhere private, it's time to make something happen. Unless the girls (and you!) are really open, nothing's likely to happen while you're all in the same room.

    That means you have to get alone.

    "Come on, I want to show you something," is a great line to tell your girl in front of the other two. "We'll be right back," you say to them, and take your girl off. Take her to another bedroom, or even a bathroom if you're in a tiny apartment and there's nowhere else to go, and just get to it as quickly as you can. If you waste time when its two guys and two girls in an apartment together, something always goes wrong -- you have to move even faster than when it's just you and a girl alone together.

There you have it. If you follow these rules, you won't just learn how to be a wingman -- you'll learn how to be a wingman extraordinaire. Guys will love having you as their partner in crime, and women will be ecstatic at your social grace -- and at your ability to lead them to what they want.

Being a good wingman isn't about being the center of attention, or being amazing at talking to girls, or any of that. All it's really about is about not stealing your pal's thunder, keeping the focus on your girl, helping to move things forward, and getting alone and giving your buddy alone time once you've gotten the girls somewhere private.

Talk to you again sometime soon.

Chase Amante

Chase AmanteAbout the Author: Chase Amante

Chase woke up one day in 2004 tired of being alone. So, he set to work and read every book he could find, studied every teacher he could meet, and talked to every girl he could talk to to figure out dating. After four years, scads of lays, and many great girlfriends (plus plenty of failures along the way), he launched this website. He will teach you everything he knows about girls in one single program in his Mastery Package.


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Anonymous's picture

Interesting point about the introductions. In the USMC, we're expected to introduce the lower-ranked officer to the senior (e.g. Colonel, I'd like you to meet Lt. So-and-so). Doing otherwise is considered disrespectful. Just goes to show even the military understands some of these social cues!

Chase Amante's picture

Ha, yep! I did some work for the US Navy for a couple of years, and when my Captain would introduce me to folks, I noticed he'd address them first if they were higher-ranked or the same rank as he was, but he'd address me first if it was a lower-ranking officer than himself.

So I'd hear, "General, this is Chase, he's doing some work for me on the XYZ project; Chase, this is General Smith," when it was someone outranking him, or I'd hear, "Chase, this is Commander Jones, he's our liaison for ABC area," when it was someone he outranked. I suppose me not having a rank but being a direct report of his he was treating me as a rank just beneath himself.

Cool insight, and thanks for your service, brother!


Danielle's picture

Full disclosure: I'm a writer who's working on a book about a girl who can't pick up men (highly unlikely, right? But that's the point; she's cursed), and I've spent the better part of the day researching what Google can tell me about being a wingman. This was by far the most useful and thought-out article I've read all day. While I'm still irritated by the very idea of men calculating their approach (I'm a woman, and you're right, we DON'T appreciate the "attraction is like math" method of thinking), I have to admit, nearly everything you wrote got a reluctant "yep, that's absolutely true" from me. Well done, sir.

I think the only addition I'd make is this: if you've engaged your target, and she's flippant or reluctant, after a couple of minutes, tell her it was nice to meet her and move on. She's probably not worth the effort if she's not eager to play with you, and you'll be wasting both her time and your time if you keep trying, and you don't want all the other women in the room to see you as "that guy who that girl keeps scowling at."

I'm hoping this was omitted from the article because it's common knowledge, but if it isn't, please take my advice and save everyone an uncomfortable confrontation. ;)

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