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Dylan and Kelly are acquaintances from childhood, with Kelly always harbouring a crush on Dylan. Despite flirting all of their sophomore year (according to Kelly and seen in episodes before Brenda and Dylan start dating), Dylan dates Brenda steadily even though Kelly tries to get a date with him afterward. 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 become attracted to each other. They connect romantically and Kelly vacillates between her attraction and feeling like she's betraying Brenda. For the sake of their friendship with Brenda, Kelly tells Dylan to forget their summer fling. When Brenda returns, Brenda and Dylan continue their relationship. Kelly's miserable and after Brenda and Dylan break up, Dylan goes straight to Kelly's house to start dating her officially. They go on a date and Brenda is shocked to see them together. The girls mend their friendship apart from Dylan. They admit their feelings to Dylan and ask him 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 towards the end when Dylan does not get into the college of his choice. When Dylan returns they reunite, until Kelly dumps him for John Sears. They get back together passionately and Dylan dumps pie on John Sears' face. The emergence of a Dylan's newfound family and Kelly's skepticism of their intentions caused a strain on their relationship. They break up at the end of their freshman year in college. Dylan falls off the wagon after being scammed by the family and wants Kelly back but she is with Brandon. When in hypnotherapy, he sees Kelly in a former life and becomes convinced 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. Antonia is killed and he leaves town. He goes to England and reunites with Brenda, Kelly hears about this from David and was visibly affected by this information despite still having feelings for Brandon. Kelly cites Dylan as her best kiss. While dating other people, Kelly has recollections of her relationship with Dylan and keeps his old letters. 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 give in to their feelings. 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.
Brenda admitted to having a fling also and breaks up with Dylan. Dylan and Kelly started 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
- mckay & taylor.
- Best Of Dylan & Kelly
- Dedicated to Dylan&Kelly
- SMUSH & RED💋SOULMATES💋