Plot
Liz Lemon (Tina Fey) comes home to find her wall full of knife holes, a great dane roaming her apartment, and a complete stranger on her bed, all courtesy of her boyfriend, Dennis Duffy (Dean Winters). She breaks up with him, but Dennis claims squatter's rights, so she gives him a week to move out. Liz and her friend, Jenna Maroney (Jane Krakowski), go out to try to pick up some men, but are very unsuccessful. The next day, Dennis walks in to the staff office of TGS with Tracy Jordan, announcing he has found a new apartment and reads a heartfelt letter to Liz. The staff suddenly turns on Liz after Dennis walks out, and Jenna suggests to Liz that in light of the previous night's disaster, she should re-consider getting back together with him. She suggests making a list of pros and cons. Liz compiles her list of pros and cons. She marks down a positive remark after coming home to find that Dennis has cleaned up the apartment, put up shelves and a TV stand, and left her dinner. In the evening, Dennis returns with an early Christmas present for Liz. She invites him in, but soon sees Dennis on Dateline's To Catch a Predator. As a result of this, Liz breaks up with Dennis, and marks it down as a con.
Meanwhile, James "Toofer" Spurlock (Keith Powell) is upset that Tracy Jordan (Tracy Morgan) is cross-dressing on TGS because it is demeaning to African-Americans. After a bit of objection, Toofer convinces Tracy to stop, handing the female character over to Josh Girard (Lonny Ross). Once Josh's character is successful, Tracy is upset with Toofer. Liz convinces Toofer to work with Tracy. As they work together, Tracy gets upset with Toofer's supposed lack of blackness, and endearingly calls Toofer a racial slur. The next morning, Jack Donaghy (Alec Baldwin), Liz, Toofer, and Tracy sit down for a meeting about Tracy's vocabulary from the previous night. Tracy and Jack point out that the African-American community has adopted the word to deprive it of its meaning. In trying to reach out to Tracy, Toofer says the word again but in a more aggressive tone of voice, which causes everyone to sympathize with Tracy. Tracy and Toofer attend sensitivity training, start arguing, and in the process develop a new sketch for TGS. When show starts running short on time, Liz offers Tracy the option to either air the sketch or one from the Star Jones cooking show, Tracy chooses the latter. Toofer is initially upset, but agrees with Tracy's decision when he finds the sketch funny.
In a subplot, Jack is secretly dating Condoleezza Rice, but gets upset when he sees Vladimir Putin touching her back. After being put on hold by Condoleezza, Jack walks into the bathroom and runs into Dennis there. Dennis, finding Jack a kindred spirit, shares his understanding of his relationship, motivating Jack to play hard to get. As a result, Jack breaks up with Condoleezza.
Read more about this topic: The Break-Up (30 Rock)
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