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* NotSoAboveItAll: 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.
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* ChekhovsLecture: 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 ''Series/{{Dateline}}'' cheating on Liz with a 16-year-old girl who he thought was 22.
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'''Man:''' [[AdaptationDisplacement What book?]]
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'''Man:''' [[AdaptationDisplacement [[invoked]][[AdaptationDisplacement What book?]]
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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:
* BeYourself: Jenna gives Liz this advice for their girls' night. It backfires.
* CategoryTraitor: 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 StopBeingStereotypical.
* EverythingIsRacist:
-->'''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.
* IncompatibleOrientation: 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.
* NWordPrivileges: 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.
* RacistGrandma: Frank thinks his racist grandfather would be amused by the conflict between Tracy and Toofer.
* RaisedAsTheOppositeGender: Josh mentions in passing that he was raised as a girl for ten years.
* SensitivityTraining: Tracy and Toofer end up here as a result of calling each the n-word.
* ShoutOut: The episode's title is probably a nod to the movie ''Film/TheBreakUp'', which came out the same year.
* StrangeMindsThinkAlike: Jack and Dennis both tell Liz that allergies are all mental.
* TheWhitestBlackGuy: 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 [[Literature/UncleTomsCabin the book]]!\\
'''Man:''' [[AdaptationDisplacement What book?]]
!!Tropes present in this episode:
* BeYourself: Jenna gives Liz this advice for their girls' night. It backfires.
* CategoryTraitor: 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 StopBeingStereotypical.
* EverythingIsRacist:
-->'''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.
* IncompatibleOrientation: 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.
* NWordPrivileges: 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.
* RacistGrandma: Frank thinks his racist grandfather would be amused by the conflict between Tracy and Toofer.
* RaisedAsTheOppositeGender: Josh mentions in passing that he was raised as a girl for ten years.
* SensitivityTraining: Tracy and Toofer end up here as a result of calling each the n-word.
* ShoutOut: The episode's title is probably a nod to the movie ''Film/TheBreakUp'', which came out the same year.
* StrangeMindsThinkAlike: Jack and Dennis both tell Liz that allergies are all mental.
* TheWhitestBlackGuy: 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 [[Literature/UncleTomsCabin the book]]!\\
'''Man:''' [[AdaptationDisplacement What book?]]
