Finally fed up with the boorish antics of her beeper salesman boyfriend Dennis (Dean Winters), Liz (Tina Fey) sends him packing and attempts to hit the New York singles scene under the guidance of Jenna (Jane Krakowski). Meanwhile, Jack (Alec Baldwin) deals with his own relationship woes, as he discovers dating a high-ranking official in the Bush Administration may be more difficult than he first thought. The war of words between Toofer (Keith Powell) and Tracy (Tracy Morgan) escalates, forcing some much-needed sensitivity training for the two cast members.

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