The friendship between Arthur Kobalewscuy and Caitlin Ryan began sometime during Season 2 of Degrassi High. Arthur developed a crush on Caitlin but she didn't feel the same way, which left him heartbroken.
Degrassi Junior High Season 1
Degrassi Junior High Season 3
Degrassi High Season 1
In Dream On, Arthur has a crush on Caitlin and always dreams about kissing her though his dreams ends before he could. At school, Arthur watches Caitlin coming down the hall. As she goes into the class, Arthur opens the door for her but accidentally bumps into her head when she drops her books. In French class, their teacher pairs them up together. They have to put on a telephone conversation. During lunch, Arthur suggests that they should work on their project at his house but Caitlin says that they can work on their project during school on Friday. Arthur then overhears Caitlin talking to Maya Goldberg talking about of how her relationship with Joey is getting rocky which makes him happy because he believes that Caitlin is interested in him when its really Claude Tanner. Arthur tells Yick Yu that he likes Caitlin and that she's going to break up with Joey for him. When they go into the classroom, Arthur approaches Caitlin and asks her when they are going to work on their French project saying that he "forgot." Caitlin tells him that they're gonna work on it this afternoon and he walks away. Maya tells Caitlin that she believes that Arthur has a crush on her but Caitlin says that she hopes not as she says that Arthur is not her type.
While Arthur is daydreaming, he dreams of him and Caitlin on a fancy date in a French restaurant and a violinist plays for them. They bring Joey out, tied to a chair and gagged. He tries to scream as Arthur and Caitlin are about to kiss until Arthur is snapped out of his dream. At the library, while they are working on the project, Caitlin asks for Arthur's help. She wants him to help her lie to Joey by canceling going on a movie date with him, though she didn't tell him that she's going with Claude. Arthur tells her that he's not good at lying but she tells him that she'll do all the talking. Arthur then agrees to help. At the movie theaters, Joey arrives, and Caitlin tells him that she needs to cancel the date so she and Arthur can work on their assignment. The next day, Caitlin asks Arthur when does he want to work on their project and they agree to finish it on Monday morning. Arthur asks her out to go see a movie but Caitlin says that she only likes him as a friend which makes Arthur feel heartbroken. He then watches her going to Claude who was waiting for her. The next day, Caitlin asks Arthur where he was this morning as they were supposed to finish their project. Arthur tells her that he already finished it. Caitlin thanks him, tells him that he's great and kisses him on the cheek. Arthur then sadly watches her go.
Degrassi High Season 2
In The All Nighter, Arthur played poker with Joey, Yick Yu and Luke Matthews at Luke's house. When discussing girls, Arthur mentioned that he still had a crush on Caitlin. Joey described her as "the Ice Princess."
- Arthur disliked Caitlin's ex-boyfriend Joey Jeremiah, who used to bully him, but they eventually became friends.
- They attended Degrassi Junior High School and Degrassi High School together from 1987 to 1991.
- Arthur thought that Caitlin liked him as he overheard that her relationship with Joey was getting rocky. She was in fact talking about Claude Tanner.
- Arthur would dream about Caitlin and tries to kiss her though his dreams get interrupted.
- Arthur and Caitlin's friendship is similar to that of Emma Nelson and Toby Isaacs. Coincidentally, Caitlin was a friend of Emma and the best friend of her mother Christine Nelson.
- This was one of the many friendships to involve one friend having an unrequited crush on the other friend.
- They were both members of the Grade 7 class 7C from 1987 to 1988, the Grade 8 class 8A from 1988 to 1989 and the Grade 9 class 9A from 1989 to 1990.
- Although Arthur was a fan of Gourmet Scum, Caitlin hated them.
- Arthur's best friend Yick Yu and Caitlin's best friend Maya Goldberg had crushes on each other but neither of them knew it.