After losing his virginity to her, Monica's boyfriend reveals that he's a high school senior. When Phoebe temps as Chandler's secretary, she finds out a secret.

Ross becomes increasingly jealous of Rachel's new colleague, Mark, and spies on her. Monica hooks up with a co-worker, who writes her a poem with a hidden meaning. One of Joey's numerous lies on his resume is exposed when he takes part in a Broadway musical.

Monica's willpower is tested when she runs into Richard at the video store. Rachel agrees to read The Shining if Joey reads Little Women. Phoebe's athletic date has a problem with short shorts.

Phoebe is reunited with her former singing partner who thinks "Smelly Cat" has hit potential; Chandler dates a woman with a prosthetic leg who also has some history with Joey. Meanwhile, Ross goes to a fashion seminar with Rachel, so she won't go with Mark, but falls asleep in the middle of it.

Monica receives a tip from an admirer worth a small fortune then goes out with the guy. A hypnosis tape intended to assist Chandler to stop smoking has a rather strange side effect. Phoebe is upset when her 18-year-old half-brother, Frank Jr., makes a surprise announcement that he is getting married - to a woman more than twice his age.

To Monica's horror, Pete wants to be the Ultimate Fighting Champion. Chandler has a problem when his new boss is slaphappy. Phoebe sets Ross up on a date with a woman who used to be bald. The group overhears a scandalous conversation at Central Perk.