What Does She See In That Guy?

In a world of Tom and Gisele, where the cheerleader always seems to go for the QB, seeing successful, strong, stunning women choose a partner without Ken-doll looks gives every guy hope. HEATHER HAVRILESKY reveals why many women find the unconventionally handsome man—or sometimes the average Joe—the best catch of all.

- Heather Havrilesky

Beautiful people fall in love every day. They spot each other in a fetid swamp of lumpy mortals and think, I’m hot, you’re hot, it is on. They’ll tell their equally attractive kids heartwarming stories about “love at first sight,” but such pairings are about as compelling as a casting agent’s daily grind. Brangelina, the Bennifers, the Hiddleswifts, the Teigen-Legends: We get it. All of your charming tales about having so much in common (“He also loves puppies! Oxygen, too!”) don’t fool us. We’ve got eyes. When you’re both supernaturally fine, your personal brands are meant to be together.

Far more intriguing are couples who aren’t a perfect match lookswise. Suddenly, there’s a riddle to solve: What the hell is she doing with him? (And vice versa, of course. But this being an aspirational magazine for men, let’s stick to the former.) The mystery intensifies when the lady in question is not only gorgeous but also smart, funny, and wildly successful, and the guy in question is a scruffy-looking dude with a dad bod, a nonexistent career, and a bad habit of showing up to red-carpet events looking like he just got off a fifteen-hour flight from Mongolia.