In his first episode, Tobey is introduced as the founder of a Gay-Straight coalition in the Capeside area that Jen drags Jack to. Tobey tries to reach out to Jack, but the other boy finds him abrasive. Tobey takes prides in his sexual orientation and uses it as his main way of identifying himself making him the foil to Jack.
Jen and Tobey begin to develop a friendship that leads her to encouraging a relationship between him and Jack. Tobey remains critical of Jack's avoidance of his sexuality, but the two begin to develop a friendship when Jack begins to volunteer with the same underprivileged youth that Tobey does. Throughout these past few months, Tobey began to develop feelings for Jack. Ironically, when Tobey is gay-bashed in the episode 'Late,' he tries to keep it to himself. Jack encourages him to go to the police for help, but Tobey is pessimistic as to whether or not they will take the event seriously because of their own homophobia.
As the school year begins to come to a close, Jack is forced by Jen to bring Tobey to his prom much against Jack's will and the two at the end share a kiss. Jack spends most of the night hesitant about whether or not to make his relationship with Tobey official because of a mix of fear due to what happened with Ethan and from other people's homophobia. By the end of the episode, Tobey is Jack's first official boyfriend. Tobey is introduced to Jack's sister, Andie, when the main cast graduates in the penultimate episode of the season.
Tobey does not appear again until his final episode, 'Use Your Disillusion.' He comes to visit Jack at Boston Bay College unannounced. Jack is in the middle of rushing his fraternity and is on call for when he is needed. When one of these calls interupts a date with Tobey, Tobey becomes passive-aggressive. Jack's other pledges, including Eric, comment on how it would be just an inappropriate if a girlfriend showed up unannounced and express their feelings on Tobey trying to both monopolize Jack's time and turn him into someone he's not. Tobey threatens Jack with an ultimatim that it is either him or the fraternity. When Jack chooses the fraternity, Tobey leaves.
- Beginning: "Promicide" (4x20)
- End: "Use Your Disillusion" (5x05)
- Reason: Jack chose his fraternity over Tobey