- Monica goes out with a guy who turns out to be a software billionaire. Chandler's stop smoking hypnosis tape has an unexpected side effect. Phoebe's brother Frank makes a surprise announcement that he is getting married - to a woman twice his age.
- Phoebe's brother Frank is getting married to a woman twice his age who used to be his teacher. Phoebe asks Joey and Ross to talk Frank out of getting married at 18. But they see that Frank really loves Alice and they agree to be best man and ring bearer. Monica is asked out by a millionaire. Chandler is using a hypnosis tape to quit smoking. The tape tells him he is "a strong confident woman" who doesn't need to smoke. He begins to act like a female.—Anonymous
- One of Monica's customers leaves her a $20,000 tip that she considers to be a joke. He turns out to be billionaire Pete Becker (Jon Favreau) who wants to date Monica (She thinks Pete wants to date her because of the blonde wig, the big boobs and the fact that she serves him food). Pete invented Moss 865, and every office in the world uses his program. Monica is really offended and confronts Pete in his office accusing him of trying to buy guys to get them to go out with him. Pete charms Monica saying that their fight is making them into a couple and he likes it. Pete convinces Monica to forget the check and asks her for one meal together.
Phoebe is shocked when her 18-year-old brother Frank Jr becomes engaged to his former teacher (She taught Home EC at Frank's school), Alice (Debra Jo Rupp), a woman more than twice his age. Frank's mother has locked him out of the house saying he is too immature to get married. They want to have kids right away. Phoebe is not OK with age difference between Alice and Frank. She speaks to Joey and Ross, who advise her not to interfere in Frank's life, but Phoebe is not convinced. She cant say anything to Frank, as she knows he will hate her.. So she begs Joey and Ross to talk him out of marrying Alice. The guys talk to Frank Jr, and tell him that he should not rush it with Alice and he should be having sex with many more women. But Frank convinces them that he really cares about Alice and sex is way better with her. Ross understands and says he had that with Rachel and he blew it. Phoebe is depressed to find out that Joey ended up being Frank's best man and Ross is his ring bearer.
Phoebe convinces Alice to come to her apartment and tell Frank why the relationship cannot work. Alice understands and decides to back off. Frank meets Phoebe and tells her that Alice called off the wedding and he is in incredible pain. His life has been chaotic with his dad leaving, arrests and a punctured lung.. He was finally happy with Alice. Frank feels betrayed when Phoebe reveals that she was the one who told Alice not to marry Frank. Phoebe brings Alice to speak to Frank, to make him realize that it was Alice's decision to back off. But it backfires as Alice and Frank start kissing and start to have sex on their sofa. Phoebe makes a quick exit from the apartment.
Chandler uses a hypnosis audio tape (given to him by Rachel. Ross thinks Hypnosis is beyond crap) while sleeping to quit smoking, but it is meant for women, which brings out his feminine side. He uses chap-stick like a lipstick, complements Rachel on her stunning blouse, wearing a towel like a woman, getting excited like a girl when Monica goes on a date with Pete. Eventually, Joey finds the tape and figures why Chandler is acting like a girl. He switches the tape with his own voice, instructing Chandler to make him a cheese sandwich everyday. Monica agrees to a date with Pete, who takes her out for pizza--in Italy.
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