James Kennedy joined the show in Season 3 when he started working at SUR at age 22. He had been dating Kristen Doute until he revealed in Season 4 that he had been cheating on her with another SUR employee, Jenna Willis. Fans watched James and Kristen split in an on-screen debacle in Season 4.
Viewers later found out that James also cheated on Raquel — in the early days of their relationship, he hooked up with Lala.