Kathy was Joey’s girlfriend whom Chandler had a crush on. Chandler hit on her before finding out that she was Joey’s latest girlfriend. He tried hard not to want to be with her, but it didn’t work. She spent a lot of time at their apartment and Chandler’s love for her grew. He bought her a first edition of The Velveteen Rabbit for her birthday and spent that night on Monica’s couch while she thanked Joey.
But one night, Joey was late for their date and Kathy was alone with Chandler in the apartment. She gave him a haircut which led to a kiss. Not wanting to hurt Joey, Chandler didn’t want to tell him about it. But when Kathy broke up with Joey because she was in love with someone else, Chandler admitted the truth to him. Furious with him, Joey made Chandler spend Thanksgiving in a box. He only forgave Chandler, when Kathy came to break up with him and Chandler, true to his word to Joey, didn’t speak.
Chandler and Kathy dated for awhile. He got sex tips from Monica and finally made love to Kathy. When watching her perform in her new play where she spends most of it having sex, Chandler became convinced she was sleeping with her co-star. They had a fight about it and Kathy did end up sleeping with him, ending her relationship with Chandler, who had been sure she was The One.

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