Season 6: Episode 134: The One With Rachel's Sister
Rachel's sister Jill, moves to New York City after their dad has cuts her off. She asks for Rachel's help in becoming financially independent, but very quickly forgets that saving money means not shopping. Ross tries to cover for Jill when Rachel sees everything she bought, but with no success. Phoebe notices a spark between Ross and Jill when Ross begins to tease Jill about her efforts to fake out Rachel. When Rachel learns that there might be something between them, she is sickened by the thought of her sister dating her ex-boyfriend. She tries to urge Jill not to be interested in Ross, but is uncomfortable with being totally honest about her reasons. Consequently, Jill misunderstands her and believes that Rachel wants her to actually ask Ross out. Reluctant to date Rachel's sister, Ross makes sure Rachel is okay with the idea, but she lies and assures him it will not be awkward. Monica is sick, but will not admit it because she believes getting sick is for weaklings. She continually tries to get Chandler into the sack to prove she's healthy, but he refuses to sleep with someone who's sick. When she finally admits to being sick and is applying Vicks Vapor Rub to her chest, Chandler gets turned on, and the tables are turned. Joey is giving away food at the coffeehouse to all the pretty women.