Dylan and Kelly have been acquaintances since childhood, with Kelly harbouring a life-long crush on Dylan.
In the summer of Senior Year, Dylan and Kelly had a summer fling while Dylan's girlfriend and Kelly's best friend Brenda was in Paris. Kelly was often the voice of reason in their relationship citing the pain they could cause Brenda if she found out but their feelings for each other always got the best of them. When Brenda returned from Paris it became difficult for Kelly to watch Brenda and Dylan together. Dylan and Brenda eventually broke up due to new found differences. Kelly later checked with Brenda that Dylan was free to date whoever he pleased and Brenda agreed. Dylan and Kelly then started dating.
Kelly then pushed Dylan to tell Brenda about his fling and he did. Brenda admitted to having a fling also and Dylan and Kelly continued their relationship. Dylan and Kelly went out on a date and while there ran into Brenda on her date. Seeing Dylan and Kelly together made Brenda feel angry and betrayed. Dylan and Kelly later told Brenda that it was her that Dylan had a fling with. Brenda being angry severed all ties with the couple. Kelly later reached out to Brenda and their friendship was repaired. The two girls later told Dylan that he would have to choose.
Meanwhile Jack McKay was released from prison. Jack later threw a party to celebrate his release. Dylan invited both Brenda and Kelly but only Kelly attended while at the party Dylan and Kelly went for a swim in the pool and Dylan told Kelly that he chose her.
Following Donna and David's wedding in 2000, Dylan and Kelly are together and eventually have a son, Sammy (Riley Thomas Stewart). Kelly would also meet her professional ambitions, leaving the fashion business behind and pursuing a Master's Degree in psychology en route to beginning her career as a guidance counselor, while Kelly, Dylan, and Sammy continued their life together. Dylan and Kelly split up and are estranged, with Kelly raising Sammy on her own.
- Luke Perry and Jennie Garth never dated off-screen
- Both Dylan and Kelly were involved in love triangles with the Walsh siblings.
- Dylan was the center of the Dylan/Brenda/Kelly love triangle.
- Kelly was the center of the Kelly/Dylan/Brandon love triangle.