Ross dumps Bonnie, which takes all night; she leaves in the morning. Meanwhile, Rachel writes a long letter to Ross that she needs him to read before they get back together; he tries to read it but falls asleep… then has to fake it when she asks him about it; Ross agrees with the letter before he finds out what it says; once he finds out the letter asks him to accept the breakup was all his fault, he’s not sure he can keep up the charade. Phoebe is upset that her real mother never tried to contact her; she tells her mother she never wants to see her again, but her mother finally convinces her to reconcile. Ursula knew about their real mother all along, but never told Phoebe. Monica, Chandler, and Joey spend the day on the beach; Joey digs a hole; Monica gets stung by a jellyfish. Joey remembers that peeing on a jellyfish sting takes the pain away; Monica “can’t bend that way” and Joey gets “Stage Fright,” leaving Chandler. Ross can’t stand hiding his feelings and he and Rachel break up again.

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Joey and Chandler agree to sell their oversized entertainment center; they have a hard time selling it but and easy time being robbed by a prospective buyer, thanks to Joey. Monica goes out with Chip, Rachel’s high school prom date; unfortunately, Chip hasn’t grown much since Lincoln High. Ross and Rachel continue to bicker about their break-up. Phoebe finds a cat and is convinced it’s her mother reincarnated; a poster is found for a missing cat, but no one has the heart to tell Phoebe… except Ross.

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Chandler and Joey try to make due with patio furniture and a canoe as their only furnishings. Chandler bumps into Joanna (Rachel’s boss) and they go out again… and end up having quite a fling; while sneaking into Joanna’s office, Rachel finds Chandler half naked and hand-cuffed to a chair. Monica caters her mother’s party and “pulls a Monica” when she loses a fake nail in one of the quiches. A salesman tries to sell Joey encyclopedias, but Joey just can’t afford a whole set.

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Joey chews out Mr. Treeger, the superintendent, for making Rachel cry; Mr. Treeger decides to evict Rachel and Monica (who have an illegal sublet of Monica’s Grandmother’s apartment). In order to smooth things over, Joey agrees to be Mr. Treeger’s practice ballroom dancing partner. Chandler tries to end his membership at his gym; Ross goes with him for moral support but ends up joining as well. Phoebe struggles (unsuccessfully) to contain her desires for Rick, one of her massage clients; she ends up being fired and he turns out to be married.

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Chandler introduces himself to a good looking girl (Kathy), only to find out that she’s dating Joey; as they get to know each other, Chandler’s feelings get deeper. Whenever Rachel is around, Ross goes out of his way to mention Amanda, a single mother he’s been seeing; Rachel counters by dating Josh, a much younger man; however, Amanda uses Ross as a babysitter so she can date another man, and Josh steals from Rachel. Ross uses weird gestures he made up as a kid instead of offensive ones. Phoebe has a bad cold which makes her singing voice sexy; when she recovers she desperately tries to catch another cold; she even kisses Gunther.

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Ross dates a fantastically beautiful paleontologist (Cheryl); everything is going great until he finds out she’s incredibly messy. Chandler buys a rare copy of Kathy’s favorite book for her birthday, but then has to make sure that Joey’s gift is good, too. Phoebe lends Monica money so she can make a more serious attempt to get her catering business going; Monica has a little trouble collecting payment from a client. Rachel strives to finish a crossword puzzle all by herself.

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Chandler becomes further frustrated when he accidentally sees Kathy coming out of the shower. Joey is late for a date with Kathy because he’s on a date with someone else; Chandler and Kathy spend time alone together and they kiss; Chandler feels so guilty that he refurnishes the apartment; Kathy breaks up with Joey, and he suspects there is another man; Chandler admits it was him, causing a rift between himself and Joey. Ross rediscovers his musical “sound,” but he isn’t really as good as he and Phoebe seem to believe; Phoebe doesn’t want to perform because she feels dwarfed by Ross’s musical gift.

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Joey is still upset at Chandler about Kathy; he tries to get over it but can’t, and decides to move out… until he and Chandler stumble upon a way for Chandler to make it up to him–spending most of Thanksgiving day in a box. Monica injures her eye but doesn’t want to have to see Richard again; she arranges to see the on-call doctor, who turns out to be very cute… and Richard’s son. The gang decides to do secret Santa for each other; Ross torments Rachel about always exchanging gifts, until she can’t stand it and shows him all the stuff she saved from their relationship.

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Phoebe and Monica buy a van (with a mural, flashing nipples, and other “extras”) for their catering business; Monica fills in for a food critic in a small local newspaper; after she gives a restaurant a scathing review, they offer her a job as the new head chef; she has to chose between it and the catering business. Ross and Chandler make plans to party with Gandolf, the party wizard; Gandolf cancels and Ross and Chandler are left bored, until Joey convinces them that they can party themselves. Rachel tries for a new position at work, but her boss doesn’t quite cooperate.

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Joey sets a personal record for sticking Oreos in his mouth–15. Ross dates a girl from Poughkeepsie but is concerned about the distance involved in seeing her. Rachel wants a relationship–or at least a fling–so Chandler offers to set her up with someone; when his coworkers find out it’s Rachel and that she’s not looking for a serious relationship, they all bribe Chandler to set them up. Monica gets no respect at work; she hires Joey in order to fire him, so everyone will know who’s boss; but Joey likes the tips, so he has a hard time going along with the plan. Phoebe works (and works and works) on a Christmas song for her friends. Ross takes a train to Poughkeepsie to break up, but falls asleep and ends up in Montreal… with a girl from Nova Scotia.

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