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In the episode, Louis meets Vanessa (played by Sarah Baker) — a funny, vivacious, pretty and open-hearted woman — at the Comedy Cellar where she is working as a waitress and he, as usual, is performing standup.
The chemistry is there, but Vanessa is fatter than women he's gone out with in the past and the idea of dating her makes him uncomfortable. And the worst part is, I'm not even supposed to do this.
On their third encounter, Louis ends up asking Vanessa out for a casual coffee, leading to one of those perfect not-dates where they wander around the city, getting to know each other and laughing at each other's jokes. Tell anyone how bad it sucks, because it's too much for people.
When Louis starts complaining about how hard it is to date in the city, Vanessa counters that his challenges are nothing compared to hers. I mean, you, you can talk into the microphone and say you can't get a date, you're overweight. But if I say it, they call the suicide hotline on me.
"Try dating in New York in your late 30s as a fat girl," she says. Louie, you know what the meanest thing is you can say to a fat girl?
Louis' immediate reaction is to tell her that she's not fat, but Vanessa, who knows she's fat and is okay with it, isn't having it and proceeds to deliver one of the best dressing downs ever seen on television.
Look, I really like you, you're truly a good guy, I think.
On behalf of all the fat girls, I'm making you represent all the guys. What is is about the basics of human happiness, feeling attractive, feeling loved, having guys chase after us, that's just not in the cards for us? Louie: You know, Vanessa, you're a very, really beautiful—Vanessa: If I was a very, really beautiful, then you would have said yes when I asked you out. But guys like you never flirt with me, because you get scared that maybe you should be with a girl like me. You know, if you were standing over there looking at us, you know what you'd see? And I mean the great looking ones, the really high-caliber studs? Because they know their status will never be questioned. Have you ever dated a girl that was heavier than you? Vanessa: No no no, I didn't say have you ever fucked a fat girl, Louie.