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Liz sets out to find the identity of a mystery number in her phone labeled "Future Husband."
Liz schedules her root canal on Valentine's Day, but has a hard time finding somebody to drive her home.
Jack struggles to find his new place in the business after hearing of the Kabletown buy out and Liz continues to wonder if Wesley is the "one."
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.