Charlie Dobbs first appearance came in "The Fake Date." There, he garnered employment at the Penalty Box. Jen had a crush on him, and received advice from Caitlin to make herself unavailable, as guys want what they can't have. To further this plan, she asked Jude to pretend to date her. Jude agreed; however, things did not turn out well, as Jude was not exactly the perfect boyfriend. Not only this, but Charlie never acted interested in dating Jen despite her having a boyfriend. At the end of the episode, Jen asked Charlie why he didn't like her only to find out that he had a girlfriend named Jill.