Ashley Kerwin:

Season 1

Ashley is on top of the world. She is the most popular girl in school and is dating the most popular boy, Jimmy. Ashley and Jimmy's relationship is strained, however. they struggle with issues of whether or not to have sex (deciding not to), and Jimmy's "clingyness." Ashley also deals with her "squeaky clean" image and is led to believe that it makes her boring. to liven things up she decides to take ecstasy at her "end of the year" party and ends up alienating her friends and cheating on and dumping Jimmy in front of everyone.

Season 2

Ashley is an outcast because of what she did at the end of last year. the only friend she has is Terri, but soon even Terri won't talk to her and instead chooses Paige and Hazel. Ashley becomes goth in her depression and befriends Ellie, the school's alterna-girl who doesn't care what anyone thinks. Ashley gradually gets her friends back and even starts to date Jimmy again, but the two have become too different to work out and she ends up connecting more with Craig instead.

Season 3

Ashley is dating Craig and on top of the world again, but things crumble quickly, when fighting with Craig leads to him cheating on her with Manny. Afterward Ashley is completely depressed and very angry with Craig, she then writes a song  to get back at him for the battle of the bands. When she loses to Craig's apology song to her she finally forgives him, but is still pretty depressed about their failed relationship and Terri being in the hospital. When Spinner and Paige take her out for the day, she begins to feel better about life.

Season 4

Once again Ashley STARTS the year out pretty content. She and Craig are best friends again, which leads to them getting back together mid-season, and a marriage proposal, which at first she rejects, but later accepts. Then the discovery of Craig's bi-polar disorder and stress from the school shooting takes its toll and Ashley needs some time away from it all. She gets an internship in England and when Craig tries to come along, she tells him no. This leaves their relationship up in the air.

Season 5
Ashley has met someone over the summer in England and decides she wants to dump Craig and stay there for the year. She returns at graduation time to find her best friend Ellie unlucky in love. She tries to help the situation, but only makes things worse... for jimmy. When he is upset and thinks no girl can ever be interested in him because of his wheelchair, she kisses him, possibly symbolizing the return of their relationship

Season 6

Ashley’s relationship with Jimmy continues into season 6. However, Ashley begins to have doubts about her abilities in sustaining a relationship. She later discovers that Jimmy has insecurities stemming from the shooting. Specifically, he is concerned about his inability to get aroused. Ashley manages to convince Jimmy that sex is not crucial in their relationship and therefore eliminates his worries.

Season 7

Ashley reprises her interest in music with the release of Craig’s first CD, which lacks credit to her for a song. Ashley recruits Jimmy and they both set out on creating a track. Ashley decides that Jimmy’s rap is not fit for the song, and removes it from the track. When she performs her version at the talent show, she is greeted with numerous boos. The minute Jimmy steps in, the crowd’s opinion is reversed. When Ellie’s roomate Griffith listens to the track, he is impressed and asks Jimmy to perform. Ashley refuses to perform with Jimmy despite his wishes, but Jimmy alone manages to gauge interest for both of them in a producer.