Toby and Rick speak to each other for the first time in Islands in the Stream. They have a bet on how many girls they can kiss and seem to bond.
In Time Stands Still (1), Toby and Rick become members of the "Whack Your Brain" quiz team. When Emma tells them that Jimmy is on the team, Toby encourages Rick to talk to Snake about the bullying, like he's said before, and to ask Snake to reconsider. However, when Rick tells Mr. Raditch about Jimmy, he brushes it off. Later that day, Toby is approached at the water fountain by Spinner, Jay, and Alex, who ask where they can find Rick. Toby refuses to tell them, and Jay pushes Toby's head into the fountain.
Toby comes over to Rick's house after school where Rick seems overjoyed over the events of the day. Rick's mother says that Rick told her that he, Jimmy, Emma, and Toby have become practically inseparable. Toby seems confused but goes along with it. Toby had seemingly been to Rick's house on at least one previous occasion as he had already met his mother.
In Time Stands Still (2), Toby is with Emma and Sean when Rick approaches them, with a gun. He tries to shoot Emma, but Sean fights him off and Rick ends up accidentally killing himself. Toby hears that Rick died from a TV reporter who asked him how he felt about it.
In Back In Black, Toby is rejected by J.T. and Danny for befriending Rick. However, J.T. eventually apologizes and goes to Rick's funeral with Toby.
- They both have had crushes on Emma Nelson.
- They both had crushes on girls who didn't like them back.
- They had a kissing contest, which Toby won.
- Toby was the only one who never had a conflict with Rick.
- They both thought that Ellie Nash was attractive.