A Cooler Version of Yourself Lyrics

Lyric discussion by just_old_light 

Cover art for A Cooler Version of Yourself lyrics by Regina Spektor

I'm not sure if I think this is about a girl's first time when she gets drunk at a party. It sounds like the protagonist sought pleasure alone, a one-night stand maybe, got wasted, and slept with a guy who thinks he's a big shot. I think "a cooler version of your dad" means that he believes himself to be an infinitely better person than his dad--and then there's "a crueler version in my mind." She sees his father's worst in him, knows he's exactly what he tries to be the opposite of. Anyway, the protagonist obviously regrets her decision (and that regret is probably amplified by the fact that it was not anonymous sex she had; this man is a part of her life; she knows him well). This song could be just a tale of disappointing sex and unfulfilling experiences.

Or maybe it's just the protagonist's opinion of men in general. She's been jaded by so many of these empty relationships, and she thinks men are all the same, they all think they're so cool, she's bored with looking for love.