The two developed mutual feelings for each other, but had to go to great lengths to hide their relationship due to the fact that it was illegal, as Matt was a student teacher in Paige's media immersion class. Their age difference greatly affected their relationship, since the two could not openly date in public. When Manny Santos caught them kissing, she exposed the couple's secret to the school after getting into an altercation with Paige. At first, Matt tried to protect his job, and said that Paige had been stalking him. Later, he broke down and revealed their illicit relationship. He was fired from his job, and the couple openly started seeing each other. At the end of the fourth season, Matt left Toronto for the summer to plant trees in the Yukon. When he returned in Season 5, he broke up with Paige, as he already had a new job lined up, and told Paige that he couldn't live the structured life she wanted. He left Paige a bag of marijuana as a parting gift.
Season 4In Neutron Dance, Paige joins Hazel at yoga class, and develops a crush on Matt Oleander, Degrassi's new Teaching Assistant. That night, Paige and Hazel use fake ID's to sneak into the bar that Matt is at. There, we find out that he is dating a woman named Charlie.
In Bark at the Moon, Paige tries to get partnered up with Mr. Oleander, and it seems that he is also interested in her. The two begin to date.In Queen of Hearts, Paige and Matt are having a secret relationship, but the two are having difficulty finding any place private where they can be together, even resorting to secret meetings in the boiler room. Their dates are continuously interrupted, and when Matt stands Paige up on one date, she wonders if he still seeing his ex-girlfriend behind her back. She goes to his apartment to confront him, but discovers he lives in a poor, beat-down apartment with a leaky roof. Realizing she wasn't trusting him, the two's relationship becomes even stronger as Paige uncovers the side of him that he had been hiding.
In Modern Love, Paige and Matt are trying to keep their relationship a secret, but it seems that it's impossible when Mr. Simpson spots them at a park. After Manny tells Hazel about Paige and Matt's relationship, Paige and Manny get into a fight at school. Matt breaks the two of them up, and Manny shouts, “HEY MR PEDOPHILE, I MEAN OLEANDER. Don’t make your girlfriend Paige even more jealous of me!” She and Matt get sent to Mrs. Hatzilakos' office. However, Matt denies that they were dating, and says that she was stalking him. However, later in the episode he admits that they dated and he is fired. They continue to date.
Season 5In Death of a Disco Dancer, Paige is eager to see Matt for their "life-changing date." After hurrying and getting ready, it takes Matt some time to show up, leaving Paige thinking that she has been stood up for a while. Finally, Matt shows up, and Paige kisses his neck.. Matt tells her that he has come straight from the airport, and they kiss, with Paige commenting on his scratchy beard and longer hair. She gives him the gift of an organizer because she said he has commented that his life is chaos, leaving him to say that he wasn't complaining about it. Paige drops the bombshell that she is applying for Banting University, and that she was hoping he would move to Kingston with her. Matt tells her his life isn't set like Paige's, as he is re-evaluating things. He tells her he has a friend in Vancouver who is getting him a job to paint houses, and Paige realizes he is breaking up with her, as they won't be able to see each other. Matt gives her a parting gift of marijuana after dumping her, which angers her since she was hoping that he was wanting to be with her, too. Talking to Marco the next day, she reveals that the night was humiliating and that she spent the entire night crying.
- They were the first student/teacher relationship in the franchise. The three other student/teacher relationships being Manny and Mick, Sav and Winnie, and Tristan and Grant.
- Start Up: Bark at the Moon (413)
- Broke Up: Death of a Disco Dancer (503)
- Reason: After a long time apart from Paige, Matt found Paige's life to be too structured and orderly.