Ashley and Liberty became aquainted in the first season. They never had a close friendship, but they were seen interacting in the earlier seasons many times. They were both involved in many extra-curricular activities in school and known as the "smart kids" in their grades. While Ashley was high on ecstacy, she told Liberty that she thought they were the same exact person. Later, Ashley is shown expressing concern for Liberty when rumors spread about a relationship between her and Coach Armstrong. The girls do not have much interaction again until Ashley joins Liberty on a trip to Smithdale over spring break.
In Family Politics, they meet for the first time. Liberty introduces herself to Ashley and talks about what might happen if Ashley is elected class president and if she is elected as secretary.
In Basketball Diaries, Liberty is fed up with having to constantly write the morning announcements for Ashley, but not get any credit for it. Liberty goes on a strike and refuses to write until she gets a turn to be on the announcements herself. Ashley gives in, but Liberty makes a huge fool of herself and is embarrassed. Everyone is making fun of her for messing up, and she runs to the bathroom crying. Ashley finds her in the bathroom and tries to comfort her. Ashley says that Liberty wasn't that bad for a first time and offers to give her pointers on how to do better. Liberty goes on the announcements once again, and she appears to have improved after taking advice from Ashley. Liberty is satisfied with her performance. Ashley tells Liberty that will be her last announcement until next year. Liberty agrees that that's fair.
In Rumours and Reputations, Ashley is one of the many people who hears about the rumour that Liberty is having an inopropriate relationship with teacher Mr. Armstrong. Ashley later confronts Liberty about it. Liberty is shocked and upset that people would think that about her when in truth, she was being tutoured by Mr. Armstrong because she has a learning dysability, dyscalculia, and it was making math harder for her.
In Cabaret, Liberty asks PMS if they'll be going on stage and Ashley says that she's not playing with the group.
In Jagged Little Pill, Liberty attends Ashley's party. Ashley, while high on ectasy, welcomes Liberty and remarks that Liberty is like a younger version of herself. She also invites Liberty to dance with her and says "Get down, Liberty!" They dance together for a little while until they both talk to other people at the party.
In The Bitterest Pill, Ashley and Liberty both attended the Degrassi memorial service for J.T. Yorke, who was murdered by a Lakehurst Secondary School student named Drake Lempkey several days earlier.
- Liberty's first line was spoken to Ashley. ("Ashley Kerwin, we haven't met. I'm Liberty Van Zandt.")
- They both served as Student Council President: Ashley from 2001 to 2002 and Liberty from 2005 to 2007.
- Liberty had a fling and was good friends with Ashley's stepbrother Toby Isaacs.
- Ashley was rivals with Liberty's close friend Manny Santos as Manny had an affair with Ashley's then boyfriend Craig Manning.
- Liberty's ex-boyfriend J.T. Yorke was best friends with Ashley's stepbrother Toby.
- They both attended J.T.'s memorial service at Degrassi in The Bitterest Pill.
- They both made their first appearances in Season 1: Ashley in Mother and Child Reunion (2) and Liberty in Family Politics.
- Ashley: "Get down, Liberty!" - Jagged Little Pill