Liz finally calls it quits with Dennis (guest star Dean Winters) while personal politics pit Toofer against Tracy --- Finally fed up with the boorish antics of her beeper salesman boyfriend Dennis, Liz sends him packing and attempts to hit the New York singles scene under the guidance of Jenna. Meanwhile, Jack 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 and Tracy escalates, forcing some much-needed sensitivity training for the two cast members.