Of all of the original students in the first season, they were the only two that were introduced into the show as a couple. In earlier seasons, their relationship did not work out because Ashley grew tired of him, and began changing as an individual, which Jimmy could not learn to accept about her. In Season 5, when Ashley returned to Degrassi after having stayed in England for a year with her father, she and Jimmy rekindled their romance. However, the fact that Ashley could walk and he could not began to take a strain on their relationship, as it made Jimmy feel like he was a burden to her. Their final break up was caused by Ashley's selfishness as well as Jimmy's rapidly developing feelings for Trina.
In Family Politics, Ashley and Jimmy are introduced onto the show as a couple, as he puts his arm around her when they are walking down the hallway together. Jimmy and his best friend Spinner Mason drag J.T. Yorke to Ashley so that she can bribe him to quit the race for student president. After school, Jimmy walks Ashley home, and congratulates her on becoming student council president and they hug.
In The Mating Game, Ashley shows Terri the necklace she got for her and Jimmy's upcoming eight month anniversary; the necklace had the letters "A" and "J" on it for the first letter of their names. For the Romeo and Juliet play, Ashley is upset she didn't get the role of Juliet, as Jimmy received the role of Romeo. In class, when Dr. Sally comes to visit and gives a sex talk, Spinner tells her "his friend" would know when to have sex, which completely embarrasses Jimmy and Ashley. When they are rehearsing the Romeo and Juliet play in class, Paige kisses Jimmy which makes Ashley jealous and she messes up her lines.
It is revealed Jimmy made Ashley a heart out of clay, as it was supposed to represent his heart, for their anniversary. Their friends pressure Jimmy and Ashley to have sex, and Ashley kisses Jimmy at his locker before telling him she is ready. Later, Jimmy asks if she's sure about tonight being the night for them and she reassures him that it is.
Ashley invites him over to have sex on their anniversary. Jimmy and Ashley both take measures to prepare. Jimmy arrives at Ashley's house and she leads him into her room and they sit on the bed together but it is awkward and neither make a move. Later, when the two are making out, Ashley suddenly leaves, but comes back in and tells Jimmy that she isn't ready to have sex. Jimmy confesses that he isn't ready either, and the two make up.
Ashley and Jimmy blow up the condoms like balloons and Toby catches them and tells them to put the condoms away before their parents arrive home. Ashley admits she thought Jimmy would dump her for Paige if she didn't give him sex but Jimmy assures Ashley he wants her not Paige. Ashley gives him her anniversary gift, and Jimmy loves it, as he kisses and hugs her in thanks.
In Basketball Diaries, Jimmy is wearing the necklace that Ashley got him from their 8 month anniversary in the previous episode.
In Coming of Age, Jimmy puts his arm Ashley as they walk to school together and Jimmy tells Ashley his mum is cooking for his 14th birthday dinner which Ashley is surprised about. At school, Jimmy kisses Ashley on the check before bailing.
Jimmy approaches Ashley at school and sits down with her before putting his arm around her. He asks if she's wants to hang out tonight but Ashley tells him she's having a girls night with Terri and he says he's cool with that. Ashley arrives at her house with Terri and sees Jimmy and Toby playing basketball together. Ashley tries to pretend that he's not there. Jimmy comes into the kitchen with Toby and Ashley is annoyed when Toby gets their mum to agree to let Jimmy stay for dinner. After dinner, Ashley and Jimmy kiss and hug goodbye.
Ashley and Jimmy's relationship is in danger when Jimmy wants to spend every day at Ashley's house. Ashley tells Terri that she's feeling smothered by Jimmy. When Toby overhears this, he decides to warn Jimmy, who in return does not take the news well. At school Jimmy tells Ashley she doesn't have to come to dinner but she tells him she will be there. On Jimmy's birthday, while at Jimmy's house, Ashley wanted to secretly give Jimmy another chance, while Jimmy gets the wrong signal and breaks up with Ashley and forces her out of his house. They later meet at Jimmy's locker, say a few heartfelt words, and she gets back together with him and they hug.
In Friday Night, Jimmy and Ashley are chatting in the hallway before they share a kiss which is rudely interrupted by their teacher Ms. Kwan. Later, Jimmy and Ashley attend class together. The next day, Jimmy and Spinner tell Ashley about their revenge on Ms. Kwan but Ashley isn't impressed. Mr. Raditch enters and tells them Ms. Kwan is taking a leave of absence and he'll be taking over their classes.
In Jagged Little Pill, Ashley's parents are out of town, and both she and Toby are allowed to have one friend over. At school, Jimmy twirls Ashley happily before she tells him she invited Terri and not him to come over tonight but he's cool about it. But later Ashley cheats and invites Paige, Terri and Hazel. Toby ends up inviting other friends as well such as J.T. and Sean.
When Ashley consumes an ecstasy tablet, she invites Jimmy and Spinner and Emma, Manny and Liberty also arrive. When Jimmy arrives, Ashley hugs him while Jimmy is surprised she hosting a party now, Jimmy asks if she's been drinking, Ashley denies it and whispers in his ear that she took Ecstasy and Jimmy wonders where she got it from and Ashley tells him Toby or J.T. Jimmy tells Ashley off and tries to drag her into the kitchen to get water but Ashley refuses before going upstairs.
Later, Ashley makes out with Sean upstairs and Jimmy see's them after and realizes what happened. Ashley follows Jimmy back downstairs and then dumps him, telling him everything she thought of their relationship which hurt him deeply. Ashley feels horrible the next day, but Jimmy doesn't want to talk to her and so their romance is over.
Season 2In Karma Chameleon, after a hard couple of months after her ecstasy problem, Ashley apologizes to Paige and Jimmy for what she did that day. Jimmy forgives her, hoping they could have another chance at love. However, when Sean asks Ashley out she says yes right away. The next day at picture day word gets around that Ashley is going out with Sean, which seems like she apologized to Jimmy for no reason and that she doesn't want a relationship with him. Eventually Jimmy calls Ashley a slut, and everyone once again turns on her, including Terri. She also chickens out on her date with Sean.
In Message in a Bottle, Jimmy has a house party, and gives a special invitation to Ashley, that is, if she wants to go. The two get back together in this episode.
In Dressed In Black, Ashley and Jimmy are finally back together, but they are having trouble reconnecting. Things are too different now that Ashley is goth. She tries changing back to her old image, but realizes things are never going to be like they once were, so she shouldn't try to change herself for Jimmy. Realizing she is being tamed, she converts back to goth style and breaks up with Jimmy.
In Rock and Roll High School, Jimmy and Ashley were, unusually, in opposing camps when Downtown Sasquatch performed in the Battle of the Bands against Ashley's anti-Craig Manning band Hell Hath No Fury. Downtown Sasquatch won the competition.
In High Fidelity (2), Ashley returns to Degrassi from London to visit with old friends and perhaps return to school the following year. Jimmy is a few credits short from graduating, and he is still feeling sorry for himself for being in a wheelchair, but encouragement from Ashley may help. Her first words of encouragement fall flat however. Jimmy likes Ellie Nash, and Ashley believes that Ellie likes Jimmy. However, it turns out Ellie actually likes Craig.
Jimmy is feeling very unattractive in his wheelchair, but a passionate kiss from Ashley boosts his confidence, not only with himself, but with his lot in life. This episode marks their third relationship.
Season 6In Can't Hardly Wait, Jimmy and Ashley's relationship is heating up; however, he is not able to get a "hard-on" or horny whenever they make love. Jimmy goes to physical therapy at lunch time, and is able to get an erection. He tells Ashley to come over to his house that night, saying that his parents aren't going to be home, telling her that it can finally work between them. He brings her to his house, and she starts the seduction. After 20 minutes, he notices that he is attracted to her, but he doesn't get an erection. Furious and embarrassed, he tells her that there is nothing she can do, and kicks her out of his house.
Jimmy apologizes to Ashley in the hall the next day, and she said she wasn't mad that he couldn't get hard, but because he kicked her out when she threw herself at him. Jimmy apologizes again, and after some talking, they both decide to seek medical help to help Jimmy with his problem.That following night, Jimmy tries out the Viagra, and Ashley gives him a massage to try to calm him down, so that the Viagra will work. He tells her that it's useless to try, and that it won't work.
Jimmy tells Ashley it's over, because he cannot satisfy her, saying that she must come over to his house and get her stuff. That night, Jimmy lets Ashley in, and they mutually agree they do not want to break up. He said that he wants to make this work, and Ashley said they will be able to, that he is all the man she has ever wanted. They go in for a kiss as the episode ends.In Working for the Weekend, in Media Immersion, Ms. Sauvé talks to class about their career aptitude tests. Jimmy and Ashley were both pleased with their top result as future lawyers. They both decide that they want to pursue the career together and go to college. Jimmy and Ashley are seen at Spinner's locker, where he reads them a poem about his break up with Darcy. Spinner and Jimmy open a store with money from Jimmy's academic fund while Marco, Ashley, Paige, Ellie and Dylan stand by their side for support. Jimmy also says that he would like to continue the career of selling t-shirts, confusing Ashley who thought they had agreed to going to law school together. Jimmy then says that he doesn't really know, and all he wants to do is be with her.
In What's It Feel Like To Be a Ghost? (1), they both attend Craig's concert when he is back in town.
In Don't You Want Me? (2), Jimmy and Ashley are shown together at the Winter Dance.
Season 7In It's Tricky, Jimmy helps Ashley restart her music career. She decides to enter a talent show and records a song Tell Me Lies with Jimmy. When the two are asked for a demo, Ashley sends it, but first deletes Jimmy's rap.
In We Got the Beat, Jimmy and Ashley are at The Dot talking about the demo. Ashley tries to hide the fact that she deleted his rap. Later, Ashley finds Jimmy listening to the demo and she admits to deleting his rap. The two get into a fight and Ashley says that she didn't want to tell him because he's been let down too much. He replies saying that she was his biggest disappointment.
In Live to Tell, Jimmy is tired of leaning on Ashley for everything, and it doesn't help their struggling relationship. When Ashley sees Trina giving Jimmy a ride to school, Ashley is angered. When she tries to talk to Jimmy, he says that she was just a crutch, and they break up.
In Bust a Move (2), Jimmy, Ashley, and the rest of the group meets up at the Purple Dragon Mystery Concert. Inside the concert, the group waits to see who the surprise guest singer is. The guest singer is revealed to be Craig Manning, who has become famous. He gives a shout-out to Ashley. Ashley then tells a puzzled Jimmy that after they broke-up, Craig asked for her to go on tour with him and she said yes. He said to her to leave him a postcard.
In Dating 4 Dudes, Derek asks Ashley out on a date, but Ashley says that she has a boyfriend, referring to Jimmy. Derek announces he can keep a secret, and Ashley agrees to go on the date. She then proceeds to ask for her money, revealing that Derek paid her to be in the video.
In Jimmy Walks!, in a daydream, Jimmy leaps from his wheelchair and saves Ashley from falling. She calls Jimmy her superhero, and the two kiss several times.
- Ashley: "Like you said, good things come to those who wait."
Jimmy: "And I think that wait is about to end." - Can't Hardly Wait
- Jimmy: "Wherever I go, you're coming with me." - It's Tricky
- They are both talented musicians.
- They were the first couple on Degrassi: The Next Generation.
- They were pressured by their friends to have sex, but they decided not to.
- Their fathers both cheated on their mothers.
- Jimmy's first line was spoken to Ashley. ("What was that all about?")
- Ashley cheated on Jimmy with Sean Cameron, when she was high. This caused Jimmy and Sean to have a conflict but it was eventually resolved.
- They've tried to have sex twice, but never succeeded: the first time was in The Mating Game but they decided they weren't ready, and the second time was in Can't Hardly Wait only for Jimmy to back out when he wasn't able to get an erection.
- Though Jimmy stated he liked her new personality, he didn't like Ashley's goth attire.
- Both characters went to high school for five years.
- Jimmy had feelings for Ashley's best friend Ellie Nash and asked her out on a date twice. However, she rejected him on both occasions: in Weird Science because he was Ashley's ex-boyfriend and in High Fidelity (2) because she had feelings for Craig.
- Jimmy and Ashley wanted to attend NYU together, and then later go to Law School.
- They were both good friends with Ellie, Paige Michalchuk, Craig Manning (whom Ashley also dated) and Terri MacGregor.
- Ashley was good friends with Jimmy's other ex-girlfriend Hazel Aden.
- Craig included a song ("She's the Ash") about Ashley on his album Of Two Minds while he thanked Jimmy in its acknowledgements.
- Ashley's mother Kate Kerwin was very fond of Jimmy. She was very upset after he was shot by Rick Murray in Time Stands Still (2).
- They both made their first appearances in Season 1: Ashley in Mother and Child Reunion (2) and Jimmy in Family Politics.
- In The Bitterest Pill, they were both interviewed by their mutual friend Ellie Nash for The Core after J.T. Yorke was murdered by Drake Lempkey.
- They were both members of Archie Simpson's Grade 9 homeroom class 9F from 2002 to 2003.
- Like Jimmy's close friend Marco Del Rossi, Ashley served as Student Council President.
- First Relationship:
- Second Relationship:
- Third Relationship:
- Fourth Relationship: