Dylan and Kelly are acquaintances from childhood, with Kelly harbouring a life-long crush on Dylan. Despite flirting with her (at least, according to Kelly) all of their freshman year, Dylan shows no interest in dating Kelly in their sophomore year when she tries to get a date with him. As the gang starts forming, they're mostly friendly, albeit not close. When Kelly starts seeing Jake Hanson, Dylan looks out for Kelly by telling Jake to be nice to her. The summer before senior year, with Brenda in Paris, Kelly and Dylan spend time together over the summer and start flirting. They hook up and Kelly vacillates between her attraction and feeling like she's betraying Brenda. When Brenda returns, Brenda and Dylan continue their relationship. Kelly's miserable and after Brenda and Dylan break up, the girls ask Dylan to choose between them. Dylan chooses Kelly and they start a relationship.
It last until the summer before college, where they travel to Europe but fight. When Dylan returns they reunite, until Kelly dumps him for John Sears. They get back together but don't have much in common and break up at the end of their freshman year in college. Dylan falls off the wagon after being scammed and wants Kelly back. When in hypnotherapy, he sees Kelly in a former life and deduces that they're soulmates. He asks her to travel the world with her, but she says no. In their junior year of college, Dylan meets Antonia Marchette. They fall in love and marry, much to Kelly's dismay. Sadly, Antonia is killed and leaves town. He goes to England and reunites with Brenda. In 1998, Dylan returns to L.A., once again off the wagon. He and Kelly are still interested in each other and at one point cheat on their respective partners. When Kelly is raped, she turns to Dylan who is there for her. Kelly gets engaged to Matt, but eventually turns him down and chooses 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 newfound 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.
- Dylan and Kelly were involved in two love triangles with the Walsh twins:
- Dylan the center of the Dylan/Brenda/Kelly love triangle; Kelly the center of the Kelly/Dylan/Brandon love triangle.
- Dylan and Kelly being in the same kindergarten was added in Season 3, when they became romantically involved. Up until then there had been no mention of them knowing each other before high school. It is established that Kelly went to elementary school with Steve and Chuck Wilson
- In the 2008 series, 90210, Dylan and Kelly have a son named Sammy. Dylan and Kelly split up and are estranged, with Kelly raising Sammy on her own. Most fans of the show don't consider the reboot series canon.
- forbidden places | MEAT PUPPETS
- water scooter fun
- damn i wish i was your lover | SOPHIE B. HAWKINS
- at paradise cove
- start choppin' | DINOSAUR JR.
- dylan and kelly talk san francisco
- trans-island skyway | DONALD FAGEN
- at the condor's nest
- in a broken dream | PYTHON LEE JACKSON
- dylan and kelly talk at peach pit