- Chandler's plan to propose to Monica at dinner is interrupted by Richard. Joey accidentally buys a boat at a silent auction. Ross and Elizabeth's relationship comes to a crossroad.
- Tonight is the big night for Chandler: he will propose to Monica. Rachel, Phoebe and Joey go to a beneficial dinner organized by Rachel's boss. Joey bids at a silent auction because he thought you had to guess the prize and therefore buys a boat for $20,000. Just as Chandler is about to propose Richard walks into the restaurant with his girlfriend and they sit at the table next to Chandler and Monica so Chandler can't propose. Elizabeth isn't as mature as Ross had thought so he breaks up with her. Chandler doesn't want to make Monica suspicious and find out about his plan so he acts as if he was still afraid of commitment. Richard goes to see Monica at the restaurant and says he still loves her.—Anonymous
- Ross is being questioned by his friends about his relationship with Elizabeth (he is 12 yrs older to her and Monica asks if Ross sees any future with her), mainly asking if the relationship is going anywhere towards a steady relationship with a future wedding. Ross quickly claims he and Elizabeth are great together, and his friends are all wrong, until he sees her having a water balloon fight with her buddies. The fight was started by Elizabeth with some juveniles that live across the hall. Deciding she is too young (and that he cant see himself marrying Elizabeth), he breaks off the relationship. Afterward, Ross questions his decision (since Elizabeth responded very maturely to the news of the break-up), until Elizabeth confirms her immaturity by dropping water balloons on his head from her upstairs window.
Rachel takes Phoebe and Joey to a charity event (Organized by her boss and thus she is under pressure to bring people to the event) helping children, including a silent auction. While Phoebe is obviously over-drinking, Joey has bigger problems; misunderstanding the silent auction process, Joey thought that bidders guessed an object's worth, with the prize going to the person with the closest guess. Joey "guesses" $20,000 and wins a yacht. Joey doesn't have $20,000 to pay for the boat and Rachel is worried that she will look bad in front of her boss. Rachel and Joey try to convince the next highest bidder (Mr Bowmont at $18K) to buy the boat (and they will cover the different from $20K), but in the process of persuading the man of the boat's virtues (naming the boat after the wife, wind in his hair, fishing, little hats, people calling you "captain" or "cappy" when he is old), Joey changes his mind and wants it for himself, although he can barely afford it. Duly, the boat is delivered to him in NYC
After weeks of preparation (selecting the ring and hiding the whole plan from Monica), Chandler is ready to propose to Monica. While at her favorite restaurant, Chandler begins his proposal however before he can ask the question Monica's ex-boyfriend Richard (Tom Selleck) walks in and the moment is lost. They end up having dinner together (Richard was there with his date Lisa) and Chandler is never able to propose to Monica the entire night. Richard recites random poetry as his toast for the evening, which sways Monica When the others come home from the charity event, they constantly ask to see Monica's hand, thinking Chandler proposed already. Feeling that Monica will figure out that Chandler plans to propose, Joey suggests that Chandler pretend he does not care about marriage and may never want to get married. So, Chandler starts acting all aloof and casual, and says that marriage is unnecessary. Monica argues people marry to solidify their commitment, celebrate the relationship, declare your love to the world. Chandler goes Meh and Monica is disturbed to see Chandler's take on marriage, as it does not align with her own views and values towards the institution
Meanwhile, Richard approaches Monica at work and declares his love for her.
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