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Jack takes a trip down memory lane when his high school crush resurfaces in his life.
Production begins on Liz's new talk show, Dealbreakers, and she realizes what it's like to walk in Jenna's shoes.
Jenna enters in a fake relationship with James Franco while Jack tries to gain access to a drunken voicemail he left Nancy.
Jack requests that Liz cast a new actor for TGS, and Liz's subsequent search for the perfect comedian, much to the dismay of Jenna and Tracy, who fear losing their spotlight. The later half of the season focuses on two complementary story arcs: Jack's inability to choose between his two girlfriends, and Liz's inability to find a boyfriend to live up to her expectations and Jenna's relationship with a Jenna Maroney impersonator.