Months after their relationship was terminated in Matchmaker, Match Breaker, Muffy convinced Chip to call Catherine (Love Saga Origins). It turns out they were both missing each other, so they went on their first date at Young & Hip Café. Things were going great until Catherine misinterpreted her sister Francine hitting on Chip, which drove a wedge between them (Double Date).
In In the Hand of Fate, Catherine confronts Chip about his relationship with her sister. Francine and Catherine end up in a duel for Chip's hand, and Francine wins. Catherine becomes bitter and depressed, and attempts suicide. Chip realizes his mistake, and breaks up with Francine to save Catherine at the last moment. Their love blossomed from there (The Darkest Hour).
In A House Divided, Muffy and Francine decide that they don't want to be sisters anymore, so they plot to break apart their siblings' relationship. Laverne Frensky and Ed Crosswire violently separate their children, pledging to keep them apart forever. Torn from her soulmate, Catherine falls into another depression... until she receives a letter from Chip revealing that he has moved back to Tallahassee Tech. Catherine elopes to join Chip at the college (Worlds Apart).
When Catherine finally arrives to join her lost lover at Tallahassee Tech, to her horror she discovers that Chip is already engaged to a wealthy hair supermodel named Jemima (A Whole New World). This drives a wedge through their relationship and makes things awkward, causing Chip to "friend-zone" Catherine (Broken Promises).
Throughout his new life with Jemima, Chip finds himself fighting feelings for Catherine, which in turn causes Jemima to become jealous. She forces an ultimatum on Chip to choose between her and Catherine (The Choice).
After Chip comes to terms with his feelings, he dumps Jemima in front of her friends, leaving her a sobbing mess (D-Day). Believing Chip and Jemima to still be together, Catherine finally hits the breaking point, and plots to kill Jemima (On the Brink). Before Chip can find her and tell her the good news, Catherine shoots Jemima in the leg and later the head, killing her instantly. Chip then tells Catherine that he dumped Jemima (Catherine Unleashed).
Chip and Catherine appear to be together again, despite the looming reality of Jemima's murder. Catherine is brought in for questioning by the police, and she and Chip make up a fake story that Jemima "held her breath for too long." But the police see through their lie, and they arrest Catherine for murder (Catherine Cracks).
After a long four months in prison, Catherine is overjoyed when Chip comes to visit. However, he hasn't come to save her as she thought. Chip gifts Catherine a cake, and the words "It's over. We're done." are written in frosting. Catherine is speechless, and Chip reveals that he is engaged to her mother, Laverne Frensky. After Chip leaves, Catherine reveals she can escape prison through a hole in the wall behind a poster (Behind Bars).