The first thing a guy asks when his buddy meets a new girl: "Does she have cute friends?" I used to be that guy, pleading with friends to hook me up with the friend before they even banged their girl. After years of begging, I concluded: it simply doesn't happen. I've never banged a girl who was the friend of a girl my buddy dated. The math is simple: if 2 percent of all girls are cute, the odds her friend is cute might as well be zero.

Even if the friend is cute, compatibility is rare. The odds a random girl plucked from the city matches me at the slightest level is very low. That's why approaching on any night takes multiple attempts until I find a seed worth watering. Compatibility can't be forced through social connection. Most wingman setups pair incompatible people and expect proximity to generate attraction. It doesn't work that way.

Girls are hesitant to go full steam with a guy who's close buddies with her girlfriend's boyfriend. Even though drama and jealousy excite girls, don't underestimate their desire for quick sex with someone not already plugged into her social circle. Sleeping with your friend's friend creates complications—awkwardness, gossip, potential fallout. Single guys outside her world are cleaner options with fewer social consequences.

When we know our boy's girl has a friend, we think we have an "in" and can throw away early game that builds attraction. We think merely sticking out our hand and existing in her presence is sufficient. Unless she's into our look, that doesn't work. We slack on game precisely when we need it most. Wingman setups feel like shortcuts but actually require more effort because you're starting from zero attraction with added social friction.