Ben Casnocha suggests:

When you’re out on the town and want to solely optimize on picking up a woman/man for sex, travel with friends who are slightly less attractive than you. If they’re more attractive than you, you look relatively less hot. If they’re absolutely ugly, you might look relatively good but such relative benefits are outweighed by being associated with ugliness.

I’m not sure that I buy this. I think the comparative disadvantage is outweighed by the perception that you are a cool enough guy to hang out with cool-looking guys. Now if you’re all wearing Neon Genesis Evangelion shirts or are otherwise demonstrating weirdness, that could be true. Likewise if you’re all displaying utter conventionality But generally speaking it seems that one of the things that women look at when appraising a guy is whether he has friends and of what stock. In those early moments of being approached or exchanging glances to invite or discourage approachment, women have little information with which to go on which means that they have to go by their gut and a sense of the guy. Who he’s with informs that. That was the conclusion I came to, anyway, when I noticed that there was a difference in the frequency with which girls would smile at me when I was out with friends, with misfit friends, and out alone in a place where people usually go in groups.

I’m reminded a bit of some advice from my brother Mitch, who is smart as a whip, was kind of nerdy before college, and had to explicitly learn what a lot of popular people learned by touch-and-feel. He said that in a bar situation, the best place to look is at a group of women that has one extremely attractive person and then pick whoever in that group you find most attractive that is not that person. It’s kind of Roissiesque, I guess, but he found that women that expect you to approach the herd (or pick off a member of the herd) for someone else are more receptive when they find out it’s them. I never took his advice because I didn’t patrol the same sorts of venues that he did and I have always had an exceptional ability at detecting compatibility with people on scant information. In other words, I already have an idea of who might be responsive to my approaches and who won’t be. In the dating scene, I’m a niche-market product in a way that my brothers are not, so I have to take care of knowing my market rather than trying to shoehorn into a market that I am not ideal for. Whenever I tried to expand my market-presence, it rarely amounted to any good even if I did have some initial success.

I am also remember back in high school when my friend Clint and I would each lunch together. Miraculously, we found these two girls to sit with day in and day out. One was quite pretty and had a way that she dressed (stockings!) that maximized her appeal. The other would have been gorgeous wearing a paper sack and clown make-up just because she was that innately beautiful. What’s funny is that even though Stockings was perfectly suitable for either of us and indeed would have been a great catch, we both fell all over ourselves trying to impress Paper Sack. A rivalry was founded upon it, even though neither of us had even a remote shot. He would give her his pudding (which sounds hopelessly grade school, but she wanted it and he had it and he gave it to her) thus leading me to call him the Pudding-Pushing Bastard or, if she happened to be present, the PPB. Because of her proximity to beauty, Stockings only barely existed. We were dopes.

So I guess it varies as to how effective it can be to surround yourself with more or less attractive people. He’s probably right that it’s best not to surround yourself with people that will embarass you. That’s a separate lesson and one I had to learn the hard way.