Monica Potts hones in on a lot of what I like about comedian Louis C.K, but I disagree with her interpretation of this episode's ending:
The show doesn't always strike the right tone. In an episode from August, Louis follows a black cashier home from the supermarket, despite her repeated attempts to reject his advances. When they reach her door, she confronts him: "So what. You never been with a black girl before? You want to see what it's like to do it with a black girl? ... Well guess what? You don't get what you want. Not all the time." If the episode had ended there, it would have been profound. But another woman comes through the door. She is heavier, she flirts with Louis, and a sex scene with them is played for laughs.
Still, some would say, at least he went there.
I think that episode is really about the kind of cultural barriers to sexual relationships between white men and black women. Basically, Louis doesn't just follow the cashier home, he spends the entire walk/train ride peppering her with his insecurities about not meeting certain stereotypes about black masculinity that he's internalized. While he's hitting on her, he's actually sort of suggesting that she's not sophisticated enough to like someone like him. He's condescending to her, and then he's mystified by the fact that she doesn't want to sleep with him. It's a brilliant moment, because he's skewering both his sense of privilege and his own internalized racism, giving a kind of laundry list of all the reasons a white guy who has certain ideas in his head of what black men are like might be afraid to hit on a black woman he's attracted to. And while Louis the character has no idea how messed up that is, Louis the comedian clearly does.
At the end, he gets to sleep with a black woman anyway. But he's actually the object of sexual desire being acted upon, not the other way around. He gets what he wants -- but only because she wants it too. At the same time I get why Monica's uncomfortable -- it's a bit of a Dave Chappelle-type moment, where it's not clear whether a complex message is lost in the laughter at a crude punch line.