I think I've written a version of this comment four times, but I can't seem to nail it.

And I think I know why I can't say anything important on this. I am trying to describe a very niche scenario. I've played wingman a lot, I've played it for friends of all genders. I think, by and large, if you're an ethical person it's a good and noble thing to do. But the way I've done it and seen it done or had people do it for me, you have to have a lot of elements already in place. You have to have very socially-capable friends who get you and know what's up, with or without you telling them explicitly. You have to be attempting a certain kind of dating--namely hooking up--for it to even be relevant. You don't need a wingman to ask someone out for coffee, nor would a wingman on a coffee date be applicable. It's a thing you do for people who are meeting strangers they'd like to take to bed at parties or bars, so is that applicable to your life?

The job of a good wingman is to help you make bigger social maneuvers in a situation where you think you have a good chance with someone and time is sensitive. You meet someone at a party, you're hitting it off, and your friends can see you're going to make something happen and they'll generally assist you in clearing a path to the goal. Examples might include leaving so you have an excuse to spend time alone with someone. They might entertain the friends your hookup (for lack of a better term) brought with them so you two can focus on each other. I used to, when called upon, invite people back to my dorm for a party so as to give people an avenue to move from a big, noisy location to a smaller, more intimate hangout. My best friend lived across the hall from me and I used to do this for her so she'd have a reason to invite people back to her dorm without, you know, having to do that in the middle of a noisy dance floor. She'd give me a nod and I'd declare we were all headed to my place to have a drink and listen to music so she'd have a better venue, which was conveniently eight feet from her bed. It's useful for subtle, social changes that are going to help you get from point A to point B with someone you've met pretty recently.

So I think it's very useful if you're in a specific situation. You have to have those kind of friends, you have to trust your friends to be great about it, you have to be in the kind of situation where that kind of assistance is useful, you have to be interested in capitalizing on such an opportunity in a given night, and you have to not be uncomfortable with the fact that other people noticed you wanted to hook up with someone. Is that a kind of dating you're interested in? No shame in that question, but it definitely favors the bold and the horny, generally speaking. I am a serial monogamist, I always had someone serious, so this wasn't something people did for me necessarily as I wasn't really into picking strangers up at parties. But my friends DID clear social hurdles for me in non-dating related ways. Sometimes good friends would notice that I'd be annoyed at everyone hanging out on my couch on a given afternoon when I was trying to study and they'd lead the group somewhere else to give me some peace, that kind of thing. Or they'd run interference if I was getting stuck talking to someone I didn't like very much. That's basically the same idea in a different execution. To me, the whole of it is having friends who are socially competent enough to read the room and to act on your behalf when you're not able to say the thing you'd like to say. It not only requires being able to read people very well, it requires having friends who are close enough to you that they know just by the tension in your face what you're thinking. And then those same friends have to have the social grace to actually intervene without making it weird.

That's how I understand it. That's how I've done it for other people. It's dead useful when it is useful, but I am not sure it comes up all that often. And how often it comes up really depends on how you're attempting to date.