Kelly and Dylan have a son named Sammy (Riley Thomas Stewart), but Dylan departs Beverly Hills following his break-up with Kelly, heading off to travel the world in support of various causes. After leaving the fashion business behind, Kelly earns a Master's Degree in psychology and starts a career as a guidance counselor. In her 30s, Kelly is seen working as a guidance counselor at her old school, West Beverly High. She remains close to her younger half-sister Erin, a.k.a. "Silver," who attends the school. Their mother's problems with alcohol eventually prompted Kelly to bring Erin home to live with her.
Early on in the show, Kelly is reunited with her old friend Brenda, whom she helps to get a job directing a play at West Beverly. Brenda relayed a message to Kelly from Brandon, who stated that he thought she was beautiful. Kelly revealed that she, herself, had spoken to him recently over the phone. Later, while discussing Kelly's current romantic status, Brenda claimed that Kelly was still in love with Dylan, while Kelly began to suspect that Brenda was still interested in him as well. Brenda took offense to the competitive suggestion, but the women quickly reconciled before again going their separate ways. In private, Brenda was revealed to have had Dylan's number on her cell phone, which she reluctantly deleted.
Later, Brenda spent time at a party with West Beverly teacher Ryan Matthews, who Kelly had ended a relationship with earlier that day, and left with him before departing Beverly Hills. Kelly took Sammy and departed town to visit Dylan, who asked them to come and be with him in Wyoming, letting Erin remain at her house. After failing to resume a romantic relationship with Dylan, Kelly returned to Beverly Hills, "open to all possibilities." She indicated to Ryan that she would like to restart their relationship, but learned that he was already dating someone, and found him to be generally distant. Brenda herself returned soon afterward and continued her stage work, but became mysteriously aloof. When Kelly became confused and upset, Brenda eventually revealed that she'd slept with Ryan, and had become ashamed. Kelly then walked away in silence.
Following a physical examination, Brenda learned that she couldn't have children, and revealed this during a private discussion with Kelly later. Kelly provided comfort, and the two made amends once again.
Kelly was later informed by Ryan that a disturbed and shaken Silver had broken into his apartment, and then disappeared when he'd left the room after calming her down. The two then began a search. It was later revealed that Erin was suffering from bipolar disorder. After learning that Silver was at a train station, Kelly and Ryan found Erin and drove her to a hospital. They then mended their friendship.
Later, Kelly and Silver were surprised by a visit from Donna, who arrived with her and David's baby girl Ruby. Having become a successful fashion designer, Donna had been traveling the world on business. Kelly provided her with comfort after learning that she and David were in the midst of a separation. Soon afterward, David sent Donna a note expressing his affection. On the same evening, Kelly ran into Ryan again, and the two of them ended up spending a passionate evening together. Eventually, though, Kelly opted to no longer pursue a romantic relationship
While serving on duty at the West Beverly Prom, Kelly was reunited with Jen Clark, a former West Beverly student, and the sister of Silver's friend Naomi. Jen attended the prom with Ryan, who she'd begun a relationship with. Tension abounded between the women with Jen holding a grudge against Kelly because when Jen was graduating Kelly wrote her college professors and told them the type of person Jen was a girl who manipulated people to get what she wanted and that she stole a girls essay out of the teachers desk so that she would become Valedictorian. There was tension between her and Debbie because Debbie noticed that she had a crush on Harry. Kelly was present at the hospital shortly before West Beverly student Adrianna gave birth. Brenda, who'd bonded with Adrianna during the production of a play, returned as Adrianna gave the child up for adoption. Brenda then revealed that she'd adopted a little girl herself while in China.
In the second season, Kelly learned that her mother Jackie was dying. Though she was initially distant, Kelly eventually visited Jackie in the hospital in order to make amends. She arrived at an empty room, leaving her to assume at first that she'd come too late. Erin then informed her sister that their mother had been moved to another room, which led to a moment of close bonding in which Jackie declared that she was proud of Kelly. Jackie later died between her two daughters.
As the season progressed, it was further suggested that Kelly had developed romantic feelings for her old friend Harry Wilson, the married principal of West Beverly High. When confronted by Harry's wife Debbie, however, Kelly declared that she had begun letting go of the attraction. She further claimed that she would no longer let herself approach an unavailable man (a reference to her past). She and Debbie then formed a friendlier relationship. Season 2 marked Kelly's last appearance on the show.