The two formed a relationship while Paige was simultaneously dating Spinner Mason, and Jesse had just broken up with Ellie Nash. After Spinner made Paige choose between him and Jesse, she chose Jesse, ending her relationship with Spinner, leading him to nearly start a fight with Jesse over Paige out of pure jealousy. Her and Jesse exclusively dated for a short period of time, but Paige broke up with him after she realized they had nothing in common.
In Love My Way, Paige meets Jesse at The Core, and negotiates a deal for Jimmy Brooks and Spinner's T-shirt shop. Jesse later stops by the store, and shows Paige the advertisement he has placed for the store in the newspaper, saying the two may have a future together. After introducing Jesse to Alex Nuñez, Jesse tells her and Paige that he and Ellie had broken up. He leaves because he has to leave to interview a friend's band, but not before inviting Paige to come see them. Later, at the show, the two connect over their views on the band, and Paige asks him to dance. The two happily have a good time dancing. The next day, Paige tells Alex that they went back to his place had coffee, an amazing conversation, and did "other stuff," implying they had sex.The day after, the two go on another date, and decide to dance again. The following day, Paige confesses to Alex that things are becoming a bit more than casual with Jesse, as he is a bit special. Spinner gives her an ultimatum: him or Jesse, and Paige chooses Jesse, ending her relationship with Spinner. Jesse shows up at the modelling event to see Paige and write an article for The Core, and Spinner nearly starts a fight with him. Paige later tells Alex that Jesse was still interested in having a casual relationship with her.
In Sunglasses at Night, Ellie and Paige are fighting, and Ellie says that she has a way with men. Paige retorts that she and Jesse had broken up, and Ellie emphasizes that they "just" had.
In Don't You Want Me? (1), Paige mentions that she broke up with Jesse, saying she didn't believe they had anything in common.
In Roomatus Interuptus, Paige and Marco interrupt Ellie and Jesse, who were trying to have sex, to ask Ellie's opinion on whether they should have so many television channels.
In Roommate Code of Conduct, Paige confesses to Ellie that she happened to be at a show last night and she saw Jesse there. They ended up flirting, and Ellie comments, "Big city...you had to pick my ex?" Paige tells Ellie, awkwardly, that she didn't pick him, but they just happened, on a strictly casual relationship. Ellie asks about Spinner though, and tells Paige that dating two guys at once is tacky.
Paige agrees with Ellie, saying dating Jesse is against the "roommate code of conduct," and that Jesse is off-limits. Ellie gives Paige permission to date Jesse, as she was the one to dump Jesse, saying she'll just try to deal. Paige asks her if she is serious and she would only go after him if it was cool with Ellie. She tells Paige that he is never coming back to their house or anywhere where she would possibly be. Paige thanks her, and Ellie walks away, leaving Paige smiling.
- Start Up: Love My Way (616)
- Broke Up: Don't You Want Me? (1) (618)
- Reason: Paige believed that she had nothing in common with Jesse.
- Jesse also dated Paige's friend Ellie Nash.
- Jesse's friend and co-worker Eric dated Paige's best friend Marco Del Rossi.
- Jesse made his final appearance in Don't Stop Believin', in which Paige made her final regular appearance.