Kelly dates wealthy Ian Armitage and inherits his fortune when he dies in a plane crash in 1998. She then becomes romantically involved with Joey and Jessica's cousin Drew Buchanan, who is also later killed in October 1998. In early 1999, Kelly has an affair with Max Holden; she later leaves him at the altar when she realizes she is still in love with Joey. Kelly's boarding school friend Grace Monroe comes to town in 1999 and becomes engaged to Joey's brother Kevin Buchanan, but is tragically drowned the same year. Kelly and Kevin console each other as she and Joey become engaged in December 1999. That New Year's Eve, Kelly and Kevin have a few drinks and kiss. They stop themselves from making love and decide not to hurt Joey by telling him about it. Joey learns of his mother's breast cancer, and he and Kelly elope on April 14, 2000. Kelly struggles with her feelings for Kevin as she tries to make her marriage work. She ultimately confesses all to Joey, and they divorce in January 2001. Joey moves to London, and Kelly begins a relationship with Kevin. When Kevin moves to Texas to be closer to his young son Duke in March 2001, Kelly follows him in August.