Liz is finally going through with her break-up with Dennis, but is having second thoughts about it. Tracy and Toofer struggle to get along with each other, and Jack dates (off-screen) Condoleezza Rice.
Tropes present in this episode:
- Be Yourself: Jenna gives Liz this advice for their girls' night. It backfires.
- Category Traitor: Tracy and Toofer each view the other as a different kind of race traitor. Specifically, Tracy thinks Toofer has assimilated too much to white culture while Toofer thinks Tracy should Stop Being Stereotypical.
- Chekhov's Lecture: Dennis gives Jack a speech about why they shouldn't go chasing 20-year-old women to feel young, commenting that half of those women are really 16. This initially seems like a sage bit of witticism, but later Liz sees Dennis get caught on Dateline cheating on Liz with a 16-year-old girl who he thought was 22.
- Everything Is Racist:Dennis: Teddy broke his ankle running from some black guys that pulled a gun on him.
Liz: Now, why is it important to tell me that the muggers were black?
Dennis: They weren't muggers; they were cops.
Liz: So, why don't you just say he was running from some cops?
Dennis: I don't know. I mean, you're a racist for assuming that they weren't cops.- Also, Toofer thinks it's demeaning for a black comedian to do drag.
- Incompatible Orientation: During her girls' night with Jenna, Liz says to a man, "I really didn't think I was gonna meet anybody tonight, but you and I have so much in common." Then another man comes over and shares a kiss with him.
- Not So Above It All: After trying to convince Tracy not to do a sketch dressed as a woman, Toofer admits that the sketch is funny when he sees it.
- N-Word Privileges: Toofer was unaware of this trope and was thus offended when Tracy called him the n-word. After it's explained to him how the word has been reappropriated, Toofer uses it on Tracy, but it turns out Toofer is too whitified to be allowed to use it.
- Racist Grandma: Frank thinks his racist grandfather would be amused by the conflict between Tracy and Toofer.
- Raised as the Opposite Gender: Josh mentions in passing that he was raised as a girl for ten years.
- Sensitivity Training: Tracy and Toofer end up here as a result of calling each the n-word.
- Shout-Out: The episode's title is probably a nod to the movie The Break-Up, which came out the same year.
- Strange Minds Think Alike: Jack and Dennis both tell Liz that allergies are all mental.
- The Whitest Black Guy: Who else but Toofer?Tracy: Ah, dude wears khakis! Uncle Tom, party of one! Uncle Tom, party of one!
Toofer: You can't call someone that if you've never read the book!
Man: What book?
