Chandler takes Monica to her favorite restaurant to propose. Just as he is about to pop the question, Richard, Monica's ex-boyfriend interrupts them. When they return to the apartment, everyone asks to see Monica's hand as Chandler tries to tell them he didn't propose. Monica is confused by everyone's actions, which makes Chandler paranoid that she has figured things out and ruined his surprise. To try to throw Monica off track, Chandler decides to act like a guy who doesn't want to get married. Phoebe and Joey attend a charity auction for Rachel's work. Joey believes the auction is actually a guessing game and makes a $20,000 bid on a boat. Much to Rachel's dismay, Joey wins the auction, and they have to figure out a way to get out of it. When they try to unload the boat on the next higher bidder, Joey realizes he wants to keep and is willing to make payments on it. Ross decides to break up with Liz after realizing that their relationship has no future because she is so much younger than he is.