Josh Sway
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/ 7 Wingman Basics

Here are 7 basic yet critical principles of the wing-man relationship.


A wing man is a hugely valuable resource when it comes to meeting women. Unfortunately, not every wing relationship works effectively, often times, due to failing to understand some of the basics of a successful wing man relationship. Here are 7 basic principles that will help you (and/or your wing) become a better wing man.

1. You are each each others’ wings

Everything starts with this principle. A solid wing man relationship is not a one-way street. Each of you is the others’ wing, if you ask a friend to "be your wingman" then you are also saying, whether you realize it or not: "and I will be your wingman." The deeper the level of trust between both of you, the better your wingman pursuits will go. Operationally speaking, the best way to think about this is that the "wingman" is determined on a group by group basis. If you are doing really well with the woman you are talking to and your wingman is barely hanging on, then he is your wingman for that interaction. If you approach a group and your wingman is getting very strong vibes and you are not then regardless of if he "offered to wing for you", you must transition into the role of wingman, making sure he gets the girl. If both of you are doing great, you should be thinking about how to isolate and escalate, perhaps by either working together (come join us at so and so’s place/other bar).

2. Always encourage, never discourage

Approaching girls at a bar or a club can be intimidating, and it’s common to making disparaging remarks about girls there as a defensive mechanism against approach anxiety. This is one of the worst things you can do. For one, you’re not actually overcoming your approach anxiety, but just retreating into a weak defense mechanism. But more importantly, you’re putting an enormous amount of pressure on your wingman to not only approach, but to approach only women you approve of! The more you do this, the more you’re telling your wingman you’d rather just stand in the corner of the bar or club, sipping your drinks and not actually talking to girls.

It’s also possible your wingman will approach, and then crash and burn harder than Goose in Top Gun. It may be tempting to make fun of him, especially if he bombed in an especially humorous fashion, but resist the urge to do this. It’s easy to be the guy that stands back and lets his wingman be the opener, so respect the fact that your wingman had the balls to make the approach at all. Otherwise, what do you think is going to happen if you keep making fun of him? He’ll stop trying to approach girls entirely, and again, you’ll lock yourself into another night of sipping overpriced drinks and not actually talking to girls.

3. Pay attention to physical positioning

Space can be limited in a bar or a club, but that’s no excuse to have an approach go badly because of bad physical positioning, and I see this all the time. Here is a diagram that illustrates a common positioning situation:

From the image above, Scenario (1) is common, yet a terrible situation. If you want to ensure that Girl #1 is bored out of her mind and will eventually drag Girl #2 "to the bathroom", use this approach.

Scenario (2) is the gold standard. Both the guys and the girls are paired up nicely, they’re able to easily communicate with anyone else in the group, and even better, Guy #1 and Guy #2 are "blocking" any other guys from any sort of direct approach. This positioning is common sense, but it’s sometimes easy to forget about when you’re not consciously thinking about it or when approach anxiety/fear of rejection get in the way.

While the diagram indicates a "head-on" approach, you can still approach at an ‘angle’ as is commonly advised.  Just make sure you end up positioned where everyone can talk to each other.

Scenario (3) is a common situation; you can’t get to Scenario (2) because of an obstruction. No matter: position as close as you can, and then move into the positioning of Scenario (2).  If the obstruction is a physical object like a chair, you can probably just nudge it aside.  If the obstruction is an actual person, just politely ask them if they can step aside.  And Guy #1 always has the option to talk to Girl #1 from the other side of the obstruction.

4. Listen to each other

Sometimes, when I am playing wing, I can see that my friend clearly has the girl in the bag if he just makes a bold move, but I know he has a a tendency to escalate way too late. But I don’t keep this information to myself; I share it, and find a way to tell him to escalate. This is why trust is so important with wingmen; the better you know each others’ strengths and weaknesses, the better you can compensate as a wingman. Don’t be too aggressive with sharing information and don’t think you know it all, but when something is obvious, point it out! The same goes for listening. Listen to your wing. Sometimes, your wing as an observer can pick up on things you cannot or are not.

5. Don’t be afraid to adjust

One HUGE mistake men make is assuming that the first girl they approach is "their" girl and the other girl is the wing’s girl. But what are the odds your initial positioning is maximally compatible? Probably not high, so you shouldn’t hesitate to "switch" if you think it makes sense based on shared interests, chemistry, kino, interest level, etc. This is another reason why initial positioning (addressed in point #3) is so important, because good positioning will let you easily switch places and have everyone engaging with the girl they’re most compatible with.

6. Don’t leave your wingman behind too early

A very common scenario is that one guy is doing well while his wingman is not doing so well. If you’re the guy doing well but you see your wing-man is getting shut down by his girl, then you need to think fast and make a decision. If it’s late enough in the night that your wing man would be fine with you "flying solo," then you should escalate quickly because it’s only a matter of time before the girl’s friend gets bored and makes your task much harder. But if it’s early, then you may have to bail out and find another set of girls you both are more compatible with. Hitting the eject button on a promising girl sucks, but it’s even worse to be the wingman left behind the whole night. Don’t leave your wingman behind, at least not too early in the night.

7. Don’t based your humor on making fun of your wingman

Good friends will make jokes at each others’ expense all the time, but when you’re talking to girls, be careful not to overdo it. That time your friend got really drunk and puked on a police officer may be really funny, but you may not want to share that story within the first five minutes of approaching girls. The girls may laugh, but your friend may end up being more embarrassed than you realize, and the girls may get the wrong idea that he’s a raging alcoholic or something. Save the "cocky/funny" attitude and the teasing for the girls you’re talking to, not your wingman.

Winging properly is complicated business, but hopefully this guide will have gotten you started. We will have more on wingmen in future articles, so stay tuned. In the meanwhile, be sure to check out or 100% free e-book crash course on women and attraction!





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