In the Emmy Award-winning comedy's 200th episode, a jealous Ross mocks Rachel's choice of an over sensative male nanny (Freddie Prinze Jr. aka Mr. Sarah Michelle Gellar) for Emma while Phoebe must choose between 2 ardent suitors -- new friend Mike (Paul Rudd) or visiting former boyfriend David (Hank Azaria). Elsewhere, Chandler feels threatened by Monica's constant chatter about a male co-worker whose sense of humor outwits even his.

Will's budding interest in a fellow lawyer in his office is nipped upon the arrival of his firm's aggressive new boss (Gene Wilder), who whips the troops into shape and orders Will to fire his friend -- until Will discovers the real reason behind the false bravado. Meanwhile, Grace and Jack are shocked to discover that their highfalutin' pal Karen is now poorer than a church mouse -- and living in her limo.

Dr. Cox's efforts to take a stand against the evil drug companies are thwarted by the seductive charm of pharmaceutical sales rep Julie Keaton (Heather Locklear). She takes advantage of the fact that Dr. Kelso has assigned Dr. Cox to coordinate a dinner reception sponsored by the drug company to pursue Dr. Cox in other arenas. Elliot and J.D. disagree about who is the better doctor, but when Elliot disregards his advice about how to treat her patient and the patient dies, it is actually J.D. that learns a lesson about taking chances. Meanwhile, Turk tries to encourage Carla to take her career to the next level by enrolling her in a nurse practitioner course.

Dr. Corday clashes with the new surgical resident (Don Cheadle) over his intervention in the treatment of a sickly young woman (Nora Zimmett) who signs a "Do Not Resuscitate" agreement while Abby wonders aloud about the erratic behavior of her visiting brother (Thomas Everett Scott). Elsewhere, Abby feels torn when she is caught between an official nurse's complaints against Dr. Kovac, her former lover. In addition, Dr. Pratt comforts Dr. Chen after she feels threatened by a patient and Corday suspects that an unconscious, 14-year old female patient has been sexually assaulted.