Jimmy and Toby developed a close friendship during Jimmy's relationship with Ashley in middle school. Toby admired Jimmy to the point where he considered him like an older brother, though it appeared Jimmy did not feel the same way. After Ashley and Jimmy grew apart and broke up, Jimmy stopped hanging out with Toby completely, and the two became distant, almost to the point of strangers. In later seasons, Jimmy often seemed irritated when having to deal with Toby.
In The Mating Game, when Toby gets home, he heads upstairs and opens the door to Ashley's room. He finds Ashley and Jimmy playing like children with the condoms they both bought, blowing them up like balloons and shrieking in laughter. In short, behaving like the children they still are and not the adults they wanted to be. It's refreshing. Ashley sees Toby in the doorway and tries to cover for what they're doing. She and Jimmy stutter over each other, quickly fabricating a story about making decorations for the dance. Toby looks at them and asks them if they think he's an idiot. He picks up a condom up off the floor and warns them to put them away before their parents get home. But before he leaves, he has a word of warning for Jimmy. "And Jimmy, girls are not worth it. Believe me." With that he shuts the door and heads to bed. Ashley and Jimmy explode in laughter.
In Basketball Diaries, Toby cheers Jimmy on at the basketball game.In Coming of Age, Jimmy and Toby are hanging out, and the two are playing basketball on the driveway. Toby asks Ashley's mother if Jimmy can stand for dinner that night, and once she says yes, the two return to playing basketball. However, when Ashley reveals that she is feeling suffocated and is thinking about breaking up with him, Toby drops his cup in shock. Toby later approaches Jimmy at his locker, and wishes him a happy birthday. Jimmy asks if he has mastered the move he taught him, and Toby tells him he almost has. Toby then hints to Jimmy to not "suffocate" girls, and Jimmy asks him as his friend to tell him. He asks Toby if she is feeling suffocated, and Toby nods his head to all of Jimmy's questions. This upsets Jimmy and he walks away.
Later, J.T. tells Toby that he shouldn't have told Jimmy, but Manny defends Toby, saying he had to, as Jimmy is like an older brother to him. Later, Jimmy and Ashley get into an argument when Toby asks her why she is even going to Jimmy's birthday dinner if she was just going to dump him. Toby says that Jimmy is amazing, as he is nice to her and him. He tells her that you don't bring people into your life just to throw them away.
In Accidents Will Happen (1), jealous over J.T.'s popularity, Toby sets out to prove he's cool and decides to hack into the Degrassi grade system to change Jimmy's grade. However, this backfires when he accidentally adjusts Jimmy's grade to an 8888%. Raditch discovers Toby's ploy when he finds that he has logged on under his name and has meddled with the grading system. To save himself, Toby rats Jimmy out, and loses cool points when Jimmy tells him he's "100% fake." Toby and Jimmy are both punished with detention.
In Take On Me, Jimmy and Toby are in detention together, and he is evidently still angry with Toby for ratting him out. Jimmy dares Hazel to kiss Toby. However, they seem to bond over the course of the episode, though this does not show in any episodes after.
Season 4In Time Stands Still (1), as a replacement for Heather Sinclair, Jimmy reluctantly joins a team consisting of Toby, Emma Nelson, and Rick Murray for Degrassi's "Whack Your Brain" event. Jimmy is particularly upset about having to be anywhere close to Rick (whom Toby has become friends with). Later on, after Toby is confronted by Spinner and Jay concerning his friendship with Rick, he returns to his team with a bloody lip. Jimmy shows concern and asks who did this to him. From that point on, Jimmy realizes that the bullying that Rick is enduring is going too far.
Season 7It's Tricky, Toby, Jimmy, Ashley, Spinner, and Emma are all grouped together, talking about Craig Manning's new album Of Two Minds and the talent show. Later, at the show, Jimmy takes a microphone out of Toby's hand to join Ashley on stage to save her from the booing crowd, and Toby seems to enjoy Jimmy and Ashley's performance. After the show, Jimmy mentions to Ashley that Toby burned their song on a CD.
In We Built This City, the boys go to prom together and sneak with the rest of the gang to go swimming. Later they both graduate and receive their diplomas.
- Jimmy dated Toby's stepsister, Ashley Kerwin.
- They both took drugs while on a team.
- They both kissed Hazel Aden but only Jimmy dated her.
- Toby's ex-friend Rick Murray shot Jimmy in Time Stands Still (2).
- Jimmy's best friend, Spinner Mason married Toby's friend, Emma Nelson in Degrassi Takes Manhattan.
- They both graduated in the Class of 2007.
- After Jimmy and Ashley broke up at the end of Season 1, they never spoke much.
- In Coming of Age, Toby's friend Manny Santos said that Jimmy was like Toby's older brother.
- In The Lexicon of Love (1), they both attended the premiere of Jay and Silent Bob Go Canadian, Eh!.
- Jimmy was close friends with Craig Manning, who also dated Toby's stepsister Ashley.
- They both attended J.T. Yorke's funeral in The Bitterest Pill.
- In The Bitterest Pill, Jimmy was upset by the death of Toby's best friend J.T. In the same episode, they were both interviewed by Ellie Nash for The Core after J.T. was murdered by Drake Lempkey.
- They both made their first appearances in Season 1: Toby in Mother and Child Reunion (1) and Jimmy in Family Politics.
- They made their final appearances in consecutive episodes of Season 8: Jimmy in Lost in Love (1) and Toby in Lost in Love (2).