The Drew Carey Show (1995) : 7x19

Lord Mercer announces that he is making his 19-year-old daughter, Milan, the new store president. She is disgusted, but he hopes that the job will teach her some responsibility. Lord Mercer tells Drew that he must make sure Milan does a good job or lose his co-manager position. She messes up a negotiation with a union by bringing in her boyfriend, D'Artagnan, and groping him the whole time. Drew asks Kate to talk to Milan and convince her to focus on her job instead of devoting all her time to her boyfriend. Milan takes her advice and gets dumped. She forces Drew to go work at the docks. Kate feels bad for Drew and agrees to try to get D'Artagnan to take Milan back. Kate instead sleeps with D'Artagnan just because he gives her some stupid look. Milan plans to give Drew his old job back, until she learns what Kate has done. Milan vanishes on the day that her father has come in to check on her progress. Drew sees her on the edge of the building preparing to jump.