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Jack bumps Jenna's scheduled appearance on ``Late Night With Conan O'Brien'' by booking new star Tracy.
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Liz confesses she went back to her ex (Dean Winters) because he asked; Jack takes it upon himself to be Liz's mentor.
Liz dumps her beeper-salesman boyfriend and hits the New York singles scene with Jenna; Jack realizes that dating a high-ranking official in the president's administration is harder than he thought.
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