Jenner fulfilled every teenage boy's fantasy by getting with Playboy Playmate Nicole in 2008. This was back during his days on The Hills, which meant Nicole had the distinct honor of being called "such a bitch" by Kristin Cavallari on national television. (More on her next.) Still, Nicole stuck by her man, even attending the Speidi wedding, until the couple called it off in December 2009.
Laguna Beach's resident bad girl dated Jenner after meeting through her high school classmate Talan Torriero, and the teen queen bee called him her first "real love." They ended things in August 2006, though the rest was still unwritten, as Natasha Bedingfield sings: The stars continued to flirt on-screen years later on The HIlls.
For five seasons of The Hills, Conrad and Jenner led us to believe that they were soulmates torn apart by bad timing. #FBF to 2006, when Jenner told PEOPLE they were "seeing each other" and "having a great time with it." As it turns out, he never did date The Girl Who Didn't Go to Paris – or so he claims. On his podcast in 2014, Jenner said it was all for show … while L.C. insisted they were briefly an item.
Richie and Jenner went from childhood pals (her dad Lionel Richie, a longtime friend of his parents, was there when he was born) to grown-up sweethearts in August 2006. And the Simple Life star got his mom's seal of approval. "I think they're very cute," Linda Thompson said. "Will they get married? Who knows." Uh, we do. The couple split that October, though Richie posted a message to her MySpace – MySpace! We were ever so young? – insisting "we were never really together … my heart was never in it."
Did Jenner enjoy 1 Night with Paris? The world may never know. In 2008, he was photographed getting close with his ex's frenemy in Sin City on New Year's Eve. That's hot. They look like they're in the midst of a steamy kiss, but he denied locking lips with the heiress/reality star/DJ/singer. "I've never made out with Paris Hilton, so that's false," he declared. We'll take him at his word, since whatever happens in Vegas stays in Vegas.
Another mystery match: Duff and Jenner were seen partying together in West Hollywood in 2007, and an onlooker called them "inseparable." Little sister Hilary Duff tried to put the rumors to rest in a radio interview, telling Ryan Seacrest, "I would kill her! He's dated a lot of people that we know, and that is kind of awkward." Guess the alleged fling is "So Yesterday."
Credit: Imeh Akpanudosen/Getty; Chelsea Lauren/Wireimage
Yes, you read that right: Leah is happily married to Brandon Jenner now, but back when she was in fifth grade, the musician "dated" Brody … until his brother stole her away! "We were 11!" Leah explained on Brody's podcast in 2014, defending her innocence. "You don't kiss, you don't make out, you don't hold hands, you beat each other up, you play basketball!" The furthest the schoolyard crush went? Brody shot her with a BB gun. Ah, young love.