Chip was extremely popular in high school; he rode a motorcycle, which some girls nicknamed "The Chipper". He also had a job working at a movie theater, which he enjoyed because of the free popcorn and candy whenever he wanted. ("The One With The Cat") Chip and Rachel used to date, but on Thanksgiving Day, 1987, he broke up with her for a girl named Nancy Branson, because she was rumored to be a slut. After learning that is was just a rumor, he called Rachel to get back together, which she was happy to do. ("The One With All The Thanksgivings") Chip also took Rachel to the senior prom. When he didn't come to pick her up, she got very upset, and convinced he wasn't coming. Ross decided that he could take Rachel to the prom, even getting dressed in a suit and make-shifting a bouquet of flowers, but at the last minute, Chip showed up and they left before Ross could say anything. ("The One With The Prom Video") At the prom, Chip abandoned Rachel to go have sex with a girl named Amy Welsh.
In "The One With The Cat", Monica runs into Chip and they go out on a date, Monica regarding it as a chance to indulge the 'fat girl' inside her who wanted to receive such an offer as a child. On this date, Monica learns that Chip hasn't matured at all since high school; he still lives with his parents, has the same job working at the Multiplex, still stays in touch with his high school buddies and still gives wedgies. Monica later tells Rachel that "You know how I always wanted to go out with Chip Matthews in high school. Well tonight I actually went out with Chip Matthews in high school." Monica does however find happiness in the fact that she got to dump "Chip Matthews in high school."