Everything ‘How to Lose a Guy in 10 Days’ (Incorrectly) Taught Me About Love

Ostensibly, then, the underlying message of this film is that, in order to find love, you need to be yourself. But that only works if “yourself” is Cool like Andie, and not Crazy like Michelle, which is the dichotomy on which this plot is predicated. Hence, Andie’s behavior serving as a rulebook for straight women everywhere. Be like Andie to land the man, be like Michelle… and you’ll scare them all off.

I tried very hard to be a Cool Girl, particularly with the men I dated in my early 20s. I feigned an interest in sports (“Please tell me what offside means”), lied about what music I listened to (“Oh, I love obscure 1970s disco!”), and even adopted the parlance of a gamer, boasting about how brilliant I was at “COD” (Call of Duty) and how it was “so much better than Halo.” I wanted the men I dated to think I wasn’t like other girls. That my interests matched theirs and I wasn’t needy, pushy, demanding, or had any real agency whatsoever beyond that which they felt comfortable giving me. 

The sad thing is that it worked—and I saw firsthand this was something men wanted from me. Take the ex who once described his type to me as “insouciance and cheekbones,” both key Cool Girl characteristics. I had neither of them—but I followed the instructions as best I could by hiding my feelings and watching contouring videos on YouTube.

I know this might sound ridiculous. But even now, at 28, I find it hard to stop myself from putting on my Cool Girl performance when I meet someone I like. Part of the reason why is that I’m so terrified of being labeled the opposite. 

The way the film pits the behaviorx of Andie and Michelle against one another is a masterclass in internalized misogyny. Sure, they might be close friends, but there’s a clear power dynamic at play because, by dint of being “cool,” Andie is superior to Michelle, who is emotional and vulnerable, states often coded as “psycho” in the heterosexual dating game. One is acceptable and the other is not.

Don’t get me wrong, this isn’t the film’s fault—and I still love watching it. The messages it sends are not the result of poor scriptwriting, but of a deeply entrenched sexism that not many people were questioning at the time. Nonetheless, the lessons about love that it, and other parts of pop culture, taught me have been hard to shake.