Winging It

There are a lot of services popping up recently that involve single men and women “hiring” a wingperson to attend functions or social gatherings with them as a way to meet the opposite sex.

While I can see the benefit of a same sex wingperson, would the concept still work if they are someone of the opposite sex? Would a single person be hurting their chances or helping them by having an attractive man or woman with them?

The basic concept of having a wingperson of the opposite sex is that it helps someone establish social proof. If he or she can get someone that outgoing and confident and attractive to hang out with them, they they must have something going for them, right? Sure. I agree with that to some extent. Where I think it can back fire is if those being cruised and wooed by the wingperson suspect that they aren’t “just a friend.” Someone might wonder why the wingperson, who is actively puffing up their partner in crime for the night, isn’t dating them themselves. Or wait. Maybe they did date. Uh oh. Still friends with an Ex? Sending out mysterious vibes can work. But this scenario would make me suspicious. Not good. Do you see how my mind works? I don’t think I’m alone in thinking this way.

I would also think that the rapport between the wingperson and their client would have to be – or at least feel – authentic in order for them to not trip off any wires of their intended targets.Let’s say you make a successful connection thanks to your wingperson. You start dating. Hey?? What happened to that friend of yours that was with you the night we met? How come I never see them around?

Sure, the wingperson can do whatever it takes to create the idea of a there being an actual friendship. They friend request you. Maybe they take photos of you and them together so you can post them on Facebook. It could work as long as the wingperson plays it on the DL.

I don’t know. It just all feels fraught with possible landmines.

Plus, if I met someone who was gushing about how awesome their single friend was omigod you just have to meet them, my first thought would be, “Uh, what’s wrong with this picture?” Call me paranoid all you like…but if two attractive people are out at a party or bar together, and they’re both single, I’m either not going to trust the person making all the introductions because I’ll assume they are just trying to be the “cool” friend. Or I’m going to assume that there is something critically flawed about their amazing single friend.

(I know. I’m way over thinking this. This is how my mind works. Sorry.)

As my friend B. told me yesterday, I require that people in my life be very high functioning in terms of their social aptitude. It’s a blessing and a curse, folks. I’m not a stickler for money, or social status, or even looks to some degree. But if someone made an interpersonal faux pas, I was less enthused. If I said, “Hey, let’s meet for a drink” that was the guy’s cue to say, “Sure, what night works for you?” If he said that it sounds like a good idea and sends me his email address and phone number and doesn’t suggest a night or make any real effort to schedule a meet up, I go from interested to meh. I don’t not meet him, but that certainly takes the bloom off the rose for me.  Worse for me were the people who just keep emailing and trying to engage in a prolonged conversations. I have no need for pen pals. 3 emails, set up date, done. If that isn’t achieved in 3 emails, I typically bail. I wasn’t not there to chit chat. In these situations I tell a guy to follow up with me when he knows his schedule. I do not reply to further messages.

Which gets us back to the original topic of social adeptness. I see the benefit in hiring someone to help you meet people. But if you struggle in social situations and don’t have great social skills, then what? You don’t bring your wingperson on the rest of your dates, do you? The confidence you had with your wingperson probably had a lot to do with why you were able to get someone’s number or email. But if you don’t know what to do next, then what’s the point?

Okay…second topic that is somewhat related to the first one.

You often hear people lament about the fact that someone’s profile had a picture of the person posed with a member of the opposite sex. Is this really such a bad idea?

Maybe a picture where you didn’t crop out the other person is a bad idea. But what if you were to strategically crop it, making it clear that there was someone of the opposite sex in the photo with you?

Sure, we hate the idea of seeing our possible competition. It feels threatening and disrespectful. What I want to know is how many people truly dismiss someone because of a photo like this on their profile. I also want to know, if we’re all going by The Honor Code, whether or not seeing a photo like that actually motivated you to contact someone.

My guess is that men and women have very different experiences with this. I think women who post photos with guys  have better luck than the reverse. But that’s just my guess.

What has your experience been?

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17 Responses to “Winging It”

  1. irishmaninsoflo Says:

    I’m fairly sure any woman realizes if a guy appears with an attractive woman it seems to make you interested ,but any guy will tell you ,the opposite is not true ,it actually works against the lady,as 9/10 the guy will interfere(cockblock) even if he’s just a friend.

    Like or Dislike: Thumb up 9 Thumb down 0

    • Howard Says:

      It all works. Did it up to last night. I am always amazed at how much it improves her play. I used to think only I would improve my chances, but I was wrong. I tend to hang around dance circles, salsa, hustle and tango. The dynamics are a little different there. If a guy showcases how well a girl can dance, it gets the other guys wanting to dance with her. I don’t do online anymore nor speed dating. This avenue among others work pretty well for me.

      Like or Dislike: Thumb up 0 Thumb down 2

  2. Badger Says:

    I really think this all depends on who’s winging and who’s being winged. Both being a wingman and taking good advantage of a wingman are fairly advanced skills, and lousy winging abounds.

    I tend to think a lot of the pop-culture bullshit about winging is just that. I’m never going to “fall on a grenade” and seduce a woman I’m not attracted to in the interest of another guy’s shot at a lay. I’m not going to salt a man’s game, but it’s his job to get himself laid by selecting a logistically sound target, not mine to consume the attentions of other

    I don’t really do a lot of group-approach game anyway, so bringing a second dude into my 1:1 conversation invites awkwardness. I normally go out with a friend of mine, we have drinks and try to have interesting conversation, and if that vibe attracts women it’s a bonus; if not we don’t blame each other for failure. Our expectations are low so we can enjoy each other’s company.

    Compared to the machinations men have to pull off, female winging is easy – you just get the other girl to leave the conversation, then tell the guy your friend is into him and to get her number/ask her out/grab her butt/whatever.

    General wisdom among the male blogger set is that preselection really only works on women (i.e. men with attractive women around them are judged as more attractive) and that women don’t get much of a boost from being seen with attractive men.

    That is the hypothesis. I personally find this to be true for me, I have noticed the boost in attention when women see me with an attractive prospect, and I tend to recoil from women who post pictures of themselves with guys who are not obviously their brothers or fathers. (Something about not being over your ex, or having platonic male friends who are liable to become more than friends at a moment’s notice).

    Women with lots of male friends (or especially those with male roommates) are tough nuts to crack – you have to supplant not just her father or her best-remembered boyfriend but a number of men who are actively in her life from which she can get doses of masculinity. On the other hand, they might be beta orbiters so you aren’t really competing with them, but that’s a risky bet.

    As for opposite-sex wings:

    Giving off unavailable vibes to potential partners who are LTR-oriented is obviously bad.

    Giving off unavailable vibes to potential partners who are still in a self-concept of “living the single life” might get them in the “I need to win them over” mindset. But then you’re selecting for immature and non-commitment-minded people.

    For me, if I see a girl with a guy, I’m not going to make a move on her lest I stoke his ire. That’s more trouble than it’s worth imo.

    I was out with a female friend once and got talking to a young lady. I left to get a drink and when I returned my friend told me she had made it clear that we weren’t together, so I had an open alley to move on the new girl. That’s good winging, anticipating the prospect’s concerns and allaying them.

    Like or Dislike: Thumb up 6 Thumb down 3

    • Horace Says:

      Eh. I say “To each, his own.” It’s okay to have different styles. There’s no ethically or philosophically superior one.

      You’re painting a particular caricature of being a “wingman.” One in which dudes are seducing women they’re not attracted to in the interest of another guy’s shot at a lay. Seriously, who’s really doing this? For the most part, a real-world wingman is there for a sort of silent moral support, and occasionally as a diversion for a girl’s friends, but mostly as company so you’re not out at the bar alone.

      There are a lot of haters out there. Sometimes, some girl I meet in a bar and I might have a connection, but her friends don’t want to give me a chance. If one of my buddies–male or female–wants to run interference (not “fall on the grenade,” but just be sociable with them) just so that she and I get our chance, then so be it. Hugs and high fives. If love is war, then the NYC bar/club/lounge scene is the frontlines, and I’m an aging soldier. I can use a little help from time to time. And occasionally, a medic :-P

      Like or Dislike: Thumb up 3 Thumb down 0

  3. Badger Says:

    Another thing: I’m going to be honest, all these pictures of really attractive people on the posts are giving me an unrealistic image of who I should be dating/pursuing. Like when I spend more time at ATWYS, I can feel my standards for women (online or in person) rising. The photos really are of exceptionally gorgeous people.

    Like or Dislike: Thumb up 7 Thumb down 1

  4. Marshmallow Says:

    re: Dating photos with pictures of the opposite sex

    I much prefer they run the picture with the person in it rather than a photo with the person’t body cropped out except for a piece of hair and an arm.

    The only time I was turned off was when a guy had a picture in his profile of two scantily clad women sitting on his lap. You could tell by the body language that the women weren’t close friends, girlfriends or anything. Stud fail!

    Like or Dislike: Thumb up 3 Thumb down 0

    • Badger Says:

      That is funny. Preselection is dicey, it has to work on the idea that the women are organically interested in the man, just being photographed with hot women is not enough. It’s all part of that fundamental paradox, women want guys to be attractive to women without looking like they’re trying to get women. If a guy looks like he’s making an effort, it doesn’t count. It certainly doesn’t count if he gets a photo op with the GoDaddy girl or something.

      Like or Dislike: Thumb up 3 Thumb down 0

      • DrivingMeNutes Says:

        Thank you for making this point because it explains better what I could not put my finger on in my comment below. The reason “pre-selection” does not work (as well) for men online as it does in real life is that all online pictures are deliberately posted – I.e. You didn’t just happen to appear on the internet in a photograph with an attractive woman, you intentionally selected that photo and uploaded it to your profile. So, as other female commenters have observed, when you post pictures with women, it doesn’t look like you naturally have credibility with women, it looks you’re trying hard to appear that you have credibility with women. I love a good unified theory.

        Like or Dislike: Thumb up 2 Thumb down 0

  5. DrivingMeNutes Says:

    First rule of online dating: Do no harm. Why do you need to have other people in your online profile pic?

    Personally, I don’t understand the distaste some have expressed for “cropping.” My view is that there should be no one but you in your online dating pictures, no buddies of either sex and no kids. Photo-cropping is legal, avaailable and cheap. Crop everyone else out to the extent you can. And, if there’s a sliver of arm and half a chin of your ex who was leaning into you at the party when the pictyures was taken? No one cares. Or, those who do care or for whom that triggers some competitive disgust/interest are an insignificant minority not worth worrying about.

    My experience is like Badger ‘s in that “pre-selection” generally works on women and, at least for me, has the opposite effect for men. When I see an attractive woman and she is with a man, I don’t size up the man and think “he’s so attractive, she must be great.” I generally ignore the existence of the man or, at best, see him as a potential problem (i.e. too much work.). Women, on the other hand, when they see an attractive man with a woman, they look at the woman and size her up. The man then becomes more attractive. Women date to achieve status with other women. Go figure.

    With respect to online, I do not want to see another man in a woman’s online dating profile. It does not trigger interest or intringue for me, or make me wonder “gee, is that her boyfriend?” I don’t think about it that much, I just don’t care. I just move on. Too much trouble. I’m sure others do the same. Also, I can’t say for sure but I’d guess that the “pre-selection” that works in real life on women probably doesn’t work as well online. Better not to risk it. Crop everyone out.

    Well-loved. Like or Dislike: Thumb up 14 Thumb down 1

  6. LostSailor Says:

    I’ve never specifically used a “wingman” so I really can’t comment, though on at least two occasions, my ex has volunteered. She’s good that way.

    As for pics, I’m not particularly happy with my online pics, but I simply don’t have a lot of digital photos of myself, since I’m the one usually behind the camera. Those that I have are usually from a party or event and usually posed with someone else, frequently a female friend. So I crop, but it’s not always possible to crop out the other person entirely.

    When viewing a woman’s photos in an online profile, I tend to take them with a grain of salt. Is this a person who is reasonably attractive that I could be reasonably attracted to? Does she look like she makes an effort with her appearance?

    Like everyone else, I’ve dated women who don’t look much of anything like their pics. But I’ve also dated women who look much better in person than their photos. I try not to put *too* much stock in online photos; it seems to be a mixed bag. (Well, except for photos that are only blurry, dark headshots; maybe she’s concerned about privacy but it only screams that she’s hiding something.)

    Like or Dislike: Thumb up 4 Thumb down 0

  7. Eliza Says:

    Personally, if I see a profile of a man with photos of women, I interpret that as a man that is insecure, and needs some validation, and an ego boost by displaying on his profile “look over here”–”see, I can meet women”. Or I can also view that as a potential headache and added unwanted drama. If you are indeed “single”…take the time out to have a friend take a few snapshots–just of YOU, and you alone, and post those. It’s very simple, and it takes a few minutes. Not a huge commitment or project. I recently had an ex-boyfriend find me on a dating website, and he reached out (not sure why?)–since we haven’t been in touch at all…and I blocked him. There is no need to have any contact with an ex. And then I later noticed he viewed my profile, and noticed on his profile, that he had a photo of him and I? How odd. Why would a man place a photo of him and his ex-girlfriend on a singles dating site? It defeats the purpose of meeting someone online. And I agree with Lost Sailor–a photo is just that–a photo. You don’t know what that person really looks like–until you actually meet them in person. There is no substitute. You can ask 1,000 of questions, you will never know who they are–until you meet. And personality is key–you can’t guage that through a photo.

    Like or Dislike: Thumb up 3 Thumb down 0

  8. Horace Says:

    LOL. Hilarious. I should totally be a wingman-for-hire.

    The opposite sex wingman only works when it’s a man and a wingwoman. Social proof in this sense works FOR men, but doesn’t really work ON men. No man I’ve ever known would be more compelled toward a woman because she’s with a dude. If anything, it’s unattractive. In fact, if I’m flipping through OkCupid and a woman has a picture with a dude, I’m immediately turned off (regardless of who that dude ultimately is). I’m sure there’s some pseudo-evolutionary-psychology reason, like women being inherently social (and thus, able to look to accept advice, even indirectly, from other women), and men being inherently competitive (and thus, the complete opposite), or something like that.

    So women, stop posting online dating pics with dudes. And for F’s sake, don’t post pictures of your cats or kids either. Seriously. What’s wrong with you?

    That said, I have several online dating profile pics in which I’m posing with fairly attractive and young women. In the captions, I allude to how they’re friends, not lovers, so I don’t come off as a player.

    Like or Dislike: Thumb up 4 Thumb down 5

    • bill Says:

      The women provides a man a level of social status indication. If a women sees a man with a women above his league she might think he has something to offer her that another man similar to her couldn’t offer. The biggest indication is the level of resources.

      Yes this is evolution at work. A lot of people have different interpretations but this does work. This probably works for more idealize beautiful women than lesser looking women because they have been in the same situation and identify with the situation.

      Like or Dislike: Thumb up 1 Thumb down 0

  9. The D-man Says:

    A girl doesn’t need to talk a guy up to be a good wing. She just has to be engaged in the conversation. If the guy has any social skills and sense of humor at all, he’ll do fine. The purpose of the woman is to show that the guy is not a loner/weirdo.

    Like or Dislike: Thumb up 2 Thumb down 0

  10. Craig Says:

    …if I met someone who was gushing about how awesome their single friend was omigod you just have to meet them, my first thought would be, “Uh, what’s wrong with this picture?” Call me paranoid all you like…but if two attractive people are out at a party or bar together, and they’re both single, I’m either not going to trust the person making all the introductions because I’ll assume they are just trying to be the “cool” friend. Or I’m going to assume that there is something critically flawed about their amazing single friend.

    I’m going to go ahead and call you paranoid. Seeing conspiracies everywhere like this where none exist is a surefire way to die alone. Some of my best friends are attractive females – and they have introduced me to a lot of other attractive women over the years. A guy being introduced to a woman by another woman is a great icebreaker and it gives the guy instant cred as not being a creep. Lastly, my female friends have far better game with women than I do, so why wouldn’t I enlist their aid? I wouldn’t hire a stranger for this task though – that’s both creepy and pathetic.

    You often hear people lament about the fact that someone’s profile had a picture of the person posed with a member of the opposite sex. Is this really such a bad idea?

    I had a couple of pics with my female friends in my profile. I wasn’t trying prove anything. They were just really good candid photos of me that happened to have others in them. Looks a lot better than those obviously cropped photos where a chopped off hand or arm is visible. I would hope women who looked at my pics would’ve given me the benefit of the doubt that I wouldn’t be foolish enough to post a picture of myself with someone I dated. Anyone who didn’t give me that benefit wasn’t someone I would have wanted to date anyway.

    Like or Dislike: Thumb up 3 Thumb down 0

  11. Steve From the City Next Door Says:

    Having my male friend(s) always seemed to hurt my chances. My female friend seemed to help – especially the one.

    Like or Dislike: Thumb up 0 Thumb down 0

  12. offensivedan Says:

    1) A wingman can definitely improve your chances or destroy them-Choose wisely.

    I have this one friend, who is married, but has a good personality and can chat women up. We go out and his presence allows me to approach a women and her friend whether they are in a group or by theselves. He takes care of the one I’m not interested in and I chat with the one I am interested in. It works well.

    I had this other friend–actually, former friend–who was quite the oppposite. We called him teh “sexual cooler” for good reason. He would not chat with the girl I was not interested nor buy her a drink. Plus, his conversational and social skills sucked. If he could do it, he would attempt to cock block me, too. Also, he dressed awful. Anyway, as you might expect, I had no success with him. In fact, one time, iIwas chatting these two girls up and a few minutes after he sat down with us they got up and left.

    We are no longer friends.

    2) An attractive women as a wingman can help, too.

    For some reason, women always remember the good-looking female friend you happened to be out with. Women always notice this. It raises your attractiveness level and shows a women you are a cool guy and not a psycho llike so many women assume men these days are. However, it is tricky approaching women when you are with them. You have to finess it and make clear you guys are just good friends.

    3) Cropped phoos

    I found that once I posted cropped photos online that my luck improved. It works.

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