Season 3: Episode 66: The One With The Hypnosis Tape
Phoebe's half-brother, Frank, announces that he's getting married--to his high school home economics teacher who's twice is age. Phoebe wants to tell Frank not to do it, but fears Frank will hate her for it, so she asks Joey and Ross to help. They try to dissuade Frank but he convinces them that marriage is a good thing. Wanting to stop her brother from getting married so young, she has a talk with his teacher/fiancee and convinces her to call off the wedding. A customer the diner asks Monica for a date. To get her attention he leaves a check for $20,000 as a tip. Thinking it's a joke she shows it to the group, but Chandler recognizes the name on the check, Pete Becker. Pete is a software wizard whols company is worth hundreds of millions of dollars. Monica's offended. Knowing Pete is a millionaire, Rachel becomes a little too excited for Monica. Monica confronts Pete, who says he left the check because he wanted to get her attention, not buy her affection. She agrees to go out with Pete for pizza, and he takes her to a great place he knows ... in Italy. Rachel gives Chandler a hypnosis tape to help him stop smoking, but the tape is designed for women and as Chandler quits smoking he becomes more and more feminine.