Phoebe's brother Frank Jr. drops by and pays a surprise visit to his sister. Thrilled to see him, she asks him what's new, and he announces to her that he's getting married. Phoebe is excited about his fiancée, until she sees it's Alice, a woman who is 26 years Frank's senior. Notwithstanding this, Frank and Alice dig deeply into each other and want to have kids right away. Phoebe finds the whole thing sick and wants to talk sense to Frank, but doesn't as she doesn't want him to hate her. She ends up asking Joey and Ross to talk to him, but they end up best man and ring-bearer respectively. As she has to take matters into her own hands, Phoebe chooses to face Alice and tell her about her problem. Alice seems to understand and tries to talk to Frank, but their deep attraction prevents her from finishing her speech. Phoebe has no choice but to accept the marriage.
After freaking out about the only two guys she went out with in a whole year (Richard and Julio), Monica is asked out by a client at Moondance named Pete. Monica is not really interested in him until Chandler reveals to her that he's a computer engineer, creator of worldwide-used software Moss 865 and millionaire. Having a check worth $20,000 (Peter gave it to her at the diner) is no small thing to Monica but also a source of suspicion, so she faces Pete about the check thing to see if it's a ruse of his to get women to go out with him. Pete tears the check apart and reveals that he likes her and would really love to go out on a date with her. After she consents, he comes pick her at the apartment, and the two head for their first date - in Rome.
Rachel can't stand Chandler smoking anymore, Rachel hands him a hypnosis tape her friend used to play which helped her quit smoking. Chandler starts playing it every night and the results are successful, as he stops smoking. However, as the woman on the tape keeps repeating to him that he's a "strong, confident, woman", he starts turning into one. Joey notices how Chandler is becoming more and more effeminate until he wakes up one night and hears the tape. He overdubs the tape by recording himself in a message for Chandler to "make him a cheese sandwich every day" and buy him "hundreds of dollars worth of pants". Chandler wakes up.