Red Pill Roundtable: Wingman vs. Solo

This week’s Red Pill Roundtable is about Wingman vs. Solo tips. Each of the respective members of the Red Pill Roundtable, myself, Goldmund from, Kyle from and answer a few questions on rolling solo vs. with a wingman. This is another lengthy, but informative and detailed ‘think-tank’ article from varying perspectives of players around the world.


Question #1 Do you prefer to roll out solo, or with a good wing? Explain your reasoning.


At night, I’ve started to prefer going out solo. During the day, I prefer to have a wing. I’ve found it much easier to keep the right vibe at night while alone. You have music, alcohol and the women look their absolute best. During the day, it’s quiet and you have no booze. Plus, the chicks often aren’t as dressed up. I do like having a good wing as well. As long as he is competent then we get along fine. It’s easier to approach more with a wing because you can get in with larger groups. Alone anything bigger than a two-set is tough to deal with (for me).


I would say I prefer solo 80% of the time and with a good wing 20% The reason is because I’m a pretty hardcore introvert and love to sit back and observe without any distractions. When I’m traveling I really prefer being solo because ‘mysterious stranger’ game is what I am best at.


With a good wing, but good wings are really, really hard to find. Much like with girls, a really successful wing and yourself will have that cheesy thing we all call chemistry. If you find someone you gel with as a wing – hold onto him. No homo. I prefer a wing simply because it’s easier to get pumped up, it’s easier to laugh off bad approaches, and of course you have a broader range of targets (groups) to choose from.

Christian McQueen:

I rolled out solo the other night, ran into a promoter friend of mine, wound up at his table and before I knew it he gave me the table and went home. So there I was with 2 full bottles and 5 sexy Latinas. Was I technically rolling solo? I guess, but point is once you get enough places On-Lock, you’re definitely going to run into people you know in nightlife yada yada, so it’s never like you’re really alone. I prefer rolling with a wing generally, IF they actually have game. It’s hard to find a good wingman.


Question #2 Have you ever had a great wing and if you have, describe what specific qualities made them a great wingman?


My best wing ever was weird as hell. Almost 7’ tall – he was an absolute poon hound and could not read social cues to save his life. He would approach everything in sight and could get almost any girl laughing. However, he had odd tastes in women.

So he would approach a group with one cute girl and one “5” and he’d always take the five. The cute girl would always be left alone and baffled as to why her friend was talking to this weird ass tall guy and I’d swoop in to entertain and game her. I had a whole routine where I would turn his odd nature into a DHV for both of us.

We would get number after number and pulled chicks back to the crib every 3rd or 4th night. My best wing ever was always approaching, had no problem escalating quickly, could get girls laughing and truly didn’t care about quality – he just wanted to pipe.


Ha. My Uncle Tommy. A 300 lb middle-aged jovial Italian. Lover of life, heavy drinker, ex-con, storyteller extraordinaire. He will just go up to a group of girls and say “you have to meet my nephew, he’s the best” and then drag them over to me and tell stories about how I was a smart little bastard of a kid who drove the family insane with my shenanigans. I’ve picked up married women thanks to Uncle Tommy. Because he ALWAYS is in good spirits (key to attracting girls with ease), we genuinely love each others company (girls can sense this more than we can tell), we speak highly of each other (the worst thing a wing can do is talk shit or have a pissing contest with you), and makes the girls laugh (get a group of girls laughing and they will follow you anywhere).


Yes – he was from Australia and I was training him for work. We went out 4-5 nights a week for the three months he was here. He was fantastic because he knew his drawbacks (hated approaching) but once he was in, he was a charming bastard. He always had good wing “manners”; i.e. if he wasn’t making the approach he knew he was getting second pick, and we just gelled together so well. It was easy for us to play things off of each other, switch targets, etc. He also had a good sense of the situation. If he saw me gelling with two girls and my drink was low, he’d go buy me a fresh vodka tonic before coming up. When he’d come up and give it to me, it’s a huge DHV boost to me (and him, too – though less so). He knew I’d pay it back and I always did. Little things like that matter.

Christian McQueen:

Yes, I had a great wing and alas I believe he’s back in Canada now. We used to have an incredible close percentage and worked together like Jordan and Pippen. His qualities were such that we complimented each other and here’s why:

-He had major confidence (key to game)

-He was an approach machine

-We built each other up in front of girls and genuinely meant it

-We knew we were the shit when we were out and girls were for OUR entertainment

-He always had an extra condom 🙂


Question #3 Do you have more fun rolling out solo, or with a wing? Do you think that even if you have more fun, it sometimes gets in the way of your overall objective (getting laid)?


I definitely have more fun when going out with a wing. It’s just easier to stay in state if you can talk shit with your wing before approaching. If your wing is good, he’ll never get in the way of you getting laid. However, it’s easier to focus on the task at hand (getting laid) if you’re solo.


I would say that its more fun going out with a wing, because I’m not thinking as much and we can laugh at rejections or funny situations together. Sometimes its WAY too much fun and we don’t even care about getting laid anymore. The night just turns into us using girls as playthings and fucking around with them just for the laughs. But at the end of a night like that, the overall objective changed and the fun bonding experience with your wing was just as good. (I find this happens a lot the first time I go out with a wing I haven’t seen in a long time–or the first time I go out with a guy who I really click with–we have so much fun that our energy takes over and we just don’t care…my first night in LA with McQueen comes to mind…).


It’s definitely more fun with a wing but it’s definitely gotten in the way of me getting laid before. Even if you’re having a blast laughing at gone-wrong approaches, it’s easy to just keep laughing about it, drinking more, and before you know it it’s last call and you have your dick in your hands with no potential prospects. Whereas if I roll out solo, there’s only one thing on my mind, otherwise I’d rather be home sleeping.

Christian McQueen:

I 100% have more fun rolling with a wing. Is it more productive in terms of getting laid? Depends on the wing/group, but the nights are such a blast that I don’t even mind, even if I don’t score. Good times with your Rat Pack is just as important as getting laid.


Question #4 Describe qualities of a bad wingman.


Selfish. Egotistical. Boring. If your wing can’t chat up the fugly friend of the cutie you’re talk to for 20 or so minutes, he is a shit wing. Your wing also has to have competent game. If he can’t get laid some on his own, he’ll struggle to get laid while out with you. This can drag your game down.


-Talks shit about you or tries to get in to a pissing contest. I hate this one because a lot of guys will do it only when there is a girl around and will be nice to you when there are no females around. Why would I ever want to be around someone I don’t respect? Girls take notice of this very, very acutely.

-Needy/Jealous. If you are hitting it off with a chick, they get upset and pout. One of my old friends did this and it was so pathetic that I lost all respect for him and don’t go out with him anymore.

-Doesn’t understand the ‘rules’ or can’t read people. There are certain codes to go by when out. For example–the guy who approaches a group of girls gets first choice as to which one of the girls in the group he wants. The wing will distract the others while he does his thing. BUT…if his target really isn’t into him and the group dynamic changes where his original target is obviously into wing #2, it’s perfectly acceptable to pass her off without a qualm. Then wing #2 owes him an introduction in the future. There are unspoken codes to go by and its great to find someone who respects them.

-Bad breath/no style. Yep…I’ve had girls come up to me and say “your friend is nice, but he really needs to brush his teeth” or “you guys don’t look like you are friends” (because he was dressed silly).


I’ve always been more of the guy who “opens” when out with wings, so this is from my point of view.

1.) Bad transition when he enters the conversation.
2.) Is greedy. If you’re not making the approaches, I believe you don’t get first choice.
3.) Worries about money for drinks, etc. It’ll all work itself out.
4.) Teases/degrades you as a way to try to raise his status in front of the girls. This is a VERY fine line. If you’ve known each other a while and can poke innocent fun at each other – it’ll show girls that you are good friends. But all it takes is one “too deep” remark to turn sour.
5.) Can’t keep a conversation. Nothing is worse than the fly on the wall in a group of people.

Christian McQueen:

Whew, I’m about to go on a rant here…

1. Don’t be a cheap fuck. If you can’t afford a $20 cover, or tip, then you shouldn’t be out anyway. I can’t stand guys who will mooch off my generosity (and I tend to be very generous when drinking) and then bounce when the next bill comes. I’ve cut many people out of my life as of late over this obnoxious and childish behavior.

2. Lack of BASIC social skills. I’m not saying you have to be an ole G expert player just charming the panties off the go-go dancers, but come on man, have some actual social skills, as in know how to carry a fucking conversation with a girl.

3. Tries to AMOG you. First off, you’re not going to AMOG me, so let’s just end the laughable attempt. Second, it makes you look stupid because the girls can see right through this which makes them lose respect for the BOTH of us, which means aint nobody getting any sweet pink pussy.

Those are the main ones. Common sense ones like dress well, be a cool motherfucker etc, are a given.


Question #5 What is the worst cockblocking experience you’ve had with a ‘wingman’ and what did you learn from it, besides that your ‘wingman’ was an idiot.


College. House party. My good friend was recently single and wanted to go get girls. So we decided to wing each other. He has male model looks and the party was jumping. There are maybe 80 or so people, none of whom we knew outside our one other friend.

We get in with two chicks really quick. Mine was real cute, but his was a bit frumpy. A few hours of drinking, flirting and making out before we head back to their place nearby. My friend is driving. We get to their house and the plan is to all head in, but my friend just looks at the girls and says, “Have a nice night!”

My jaw drops. I tell him they invited us in. I tell him we should just have a drink with them. He just says he’s tired and wants to go home. The girls watch all of this and quickly the mood sours. I couldn’t stay the night due to the logistics of getting home the next day. So we end up driving away from two would-be-bangs due to my friend being upset he wasn’t getting with the hotter of the two girls.


Oh man, one guy comes to mind. I knew him before I really got into game and self-improvement and then when I started applying it and getting results I tried to explain it but his arrogance caused him to ignore all useful advice, so I stopped. We went on a road trip up to Maine together and were out playing pool when I spotted a sexy girl walking past us. I waved her over, started talking, and she was loving it. My ‘wing’ kept badgering me about continuing the pool game to the point where the girl said “whats the matter with your friend?”

I told her to wait by the bar for 10 mins so I could finish up. I told my friend I wanted to fuck this girl and he said “what am I supposed to do?” and I told him he should go fuck himself. I went back to the girl, talked to her for a few minutes and he came up behind me, tapped me on the shoulder and told me that we had to leave. I told him no, and turned to the girl again. He grabbed my shoulder and said he wasn’t leaving without me. I said in his ear “get the fuck out of here, I’ll take care of myself” and turned back to the girl. He left and I had to smooth things over with the girl, telling her that he had just broken up with his girlfriend (lie) and was sensitive. Needless to say, that was the last trip I took with the dude. (Yes I fucked the girl…her pussy smelled like lobster bisque).

This was a guy who was a professor of philosophy, a successful musician, and could speak 5 languages. Even though he had accomplished a lot, he was an idiot when it came to women. That’s the first time I realized that game exposes the ego more than any other endeavor.


It was actually a story with the Australian guy above and a SECOND Australian who was staying with us (also worked with him). He was older (I think 33) and we all went to Vegas to celebrate them leaving; only one room for the 3 of us (two beds, one on the floor). He went to bed one night at 1am, and my wing and I went to get into Marquee at the Cosmo. Crazy long line, but we picked up two girls from Chicago and got them back to the room without ever setting foot in the club. Once we got there, the older cat thought since that we’d woken him up, that we’d brought these girls for him and proceeded to try to make out with both of them, even after my wing and I had both chosen our targets (and made out with them). Of course, nobody got laid that night.

Obvious lesson learned was that logistics really matter. If he was out of the room, they both probably would’ve banged us on separate beds, but once he was in the equation there was no chance of it. That was my first trip to Vegas as a freshly minted 21 year old, so needless to say I’ve planned much better logistics in trips since.

Christian McQueen:

Damn, where do I start. One story that comes to mind is a cat who just did not get game for the life of him. No matter how much I taught him, no matter how many times he saw me pull girls for one night stands, he could not connect the dots. One time I pulled two girls (trying to help this motherfucker out) to one of the girl’s apartment. They were down as can be and all he needed to do was go into the girl’s room with her. I mean she was sitting on his lap, stroking his hair, EVERYTHING! He just sat there like a dumbass. Finally, I had enough. I told him to go wait downstairs in his car while I dicked out both girls. I believe that was the last time I rolled out with him. While it worked out in my favor (threesome), I just couldn’t deal with having such a dumbass roll with me, especially when I put out so much effort trying to help him. Like the old saying, you can lead a horse to water, but you can’t make them drink. Well, you can lead your buddy to the bar, but you can’t make them pick up a chick.

Note: I am traveling for the next couple of weeks, so the podcast is on hiatus until July 20th and my posting on the blog will be more sporadic as well.


5 Replies to “Red Pill Roundtable: Wingman vs. Solo”

  1. I always enjoy these round table discussions for the variety of different opinions and angles you hear. However, despite (presumably?) you all having fairly styles you seem to concur on quite a lot of things.

    Personally for me, I prefer to roll out with wings every time. Although I do like to go for a few solo nights also here and there for the practice, I often deliberately show up a couple of hours early to a venue before my wing(s) arrive to do a bit of solo gaming. It’s good to really focus your mind on approaches and managing state. Not to mention getting out of your comfort zone. Some of my best nights and pulls have been from random nights rolling solo.

    However, I have quite a solid squad of good wings based all over the world so am never short of someone to roll with. And whenever you have some buddies who are also very good at talking to women you can really leverage up on your night. Where you bring girls back to your table and they do also, then you introduce the girls to eachother. Perhaps then mentioning to one of the chicks that another of the girls found her attractive… etc 😉

    Often like Christian, whenever I’m rolling solo on home turf I will usually run into girlfriends or fellow buddies of mine, and I’ll know door/bar staff to vibe with too. So technically I guess I’m not really rolling solo in that sense. But that’s the beauty of rocking solid social circle game in your home city/cities. If you invest in building the network up front you reap the benefits later on.

    However, I also do like to take off on occasional long weekend raids on other SE Asian cities and roll solo there where nobody knows me and I don’t know anyone. There’s something incredibly liberating about being able to land in a random city one evening and then later that night you’re rocking some private afterparty with a load of random cool people you just met before taking home some beautiful chick(s) to slam…


  2. I love this interview because it shows the upsides and downsides of winging. Having a wing is overrated by the game community. ime it better to be wingless than with a shitty or mediocre wing.


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