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.

Rachel goes on her first date after splitting from Ross...and it's with Mark, her former colleague. Joey is cast in a play and develops a crush on his costar. Monica continues to date Pete, even though she is still not attracted to him.

Monica considers a dream job as head chef in Pete's new restaurant, but Phoebe fears there is more to the deal. Ross makes a sacrifice to help Rachel, who may have a broken rib. Meanwhile, Joey buys Chandler an unusual pet.

When Rachel finds out that Ross is bringing a date to the premiere of Joey's big play, she finds one of her own. Ross alone concludes that her date is insane. Poor Phoebe is on hold for days with a company she needs to talk to before her phone warranty expires. Meanwhile, Joey's play gets terrible reviews, but his co-star provides some comfort.

Afflicted with a mysterious skin condition on his butt that doctors cannot identify the cause of, Ross seeks advice from Phoebe's herbalist. Phoebe finds herself in a dilemma when she cannot choose between two guys. Monica can't decide about Pete when she thinks he is going to propose.

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.