The Break-Up

"The Break-Up" is the eighth episode of the first season of the American television comedy series 30 Rock. It was written by co-executive producers Brett Baer and Dave Finkel, and directed by Scott Ellis. The episode originally aired on NBC in the United States on December 14, 2006. Guest stars in this episode include Rachel Dratch, Chris Hansen, Keith Powell, Lonny Ross, and Dean Winters. In the episode, Liz Lemon (Tina Fey) finally dumps Dennis Duffy (Dean Winters) and prowls the singles scene, where she proves to be particularly inept at picking up guys, under Jenna Maroney's (Jane Krakowski) tutelage. Meanwhile, Tracy Jordan (Tracy Morgan) and James "Toofer" Spurlock (Keith Powell) clash, landing both in sensitivity training, and Jack Donaghy (Alec Baldwin) dates a certain "high-ranking African-American member of the Bush Administration." 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 into 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.