The Break-Up (30 Rock)
"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