David was Jack's first official boyfriend after his casual sex phase. They were first introduced in the episode 'Living Dead Girl,' by C.J at a Halloween costume party. In the next episode, David spends the night waiting for Jack at Hell's Kitchen well past the time that C.J, Audrey, and Jen leave. Jack finally shows up after he'd spent the night at a faculty function with his professor. Jack started a relationship with David because he felt the timing was better than it was with his professor.
In 'Day Out of Days,' a few months into their relationship, David and Jack go to get tested for HIV as well as other STIs. They begin discussing their respective sexual histories reavealing that Jack has much more experience than David. David and Jack broke up in the nineteenth episode, Lovelines. David assumed Jack was trying to get out of their relationship by opening flirting with Fred. The truth of the matter was that Jack was just being nice to the other guy. David made their fight public during the live Loveline show at Boston Bay College with Adam Carolla and Dr. Drew. Jen tried to defend Jack from on-stage causing the fight to subside. Afterwords, Jack tried to make light of the earlier fight causing David to blow up at him again. David remained convinced that Jack was trying to get out of the relationship and the two brok up.
In David's final appearance, Jack tries to make things right between them by inviting David out to Hell's Kitchen following his final exam. David tells him that he'll think about it. When David does arrive, he sees Jack talking to a guy from his sociology class and assumes that they were flirting. Jack tells him that the interaction was innocent causing David to ask whether or not what happened with Fred was just as innocent. David called Jack out by telling him that he was only going through the motions of a relationship because it was what he thought was right.
- Beginning: "Ego Tripping at the Gates of Hell" (6.07)
- End: "Lovelines" (6.19)