01of 08AVRIL LAVIGNEMichael Simon/Albert Ferreira/Startraks; Nick SaglimbeniLavignemadeJennerher Sk8er Boi in May 2010, when they were spotted getting cozy in the club scene. It got so serious that he took her as his date to step-sisterKim Kardashian’swedding to Kris Humphries the next year. (As we learned from her nuptials withKanye West, those plus-onesare super exclusive. Sorry, Kaitlynn!) Alas, neither relationship stood the test of time, and Jenner and the pop-punk singer broke up in January 2012.
01of 08
AVRIL LAVIGNE
Michael Simon/Albert Ferreira/Startraks; Nick Saglimbeni
LavignemadeJennerher Sk8er Boi in May 2010, when they were spotted getting cozy in the club scene. It got so serious that he took her as his date to step-sisterKim Kardashian’swedding to Kris Humphries the next year. (As we learned from her nuptials withKanye West, those plus-onesare super exclusive. Sorry, Kaitlynn!) Alas, neither relationship stood the test of time, and Jenner and the pop-punk singer broke up in January 2012.
02of 08
JAYDE NICOLE
Alexander Tamargo/Getty
03of 08KRISTIN CAVALLARIClark Samuels/StartraksLaguna Beach’sresident bad girldated 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 onThe HIlls.
03of 08
KRISTIN CAVALLARI
Clark Samuels/Startraks
Laguna Beach’sresident bad girldated 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 onThe HIlls.
04of 08
LAUREN CONRAD
Chris Polk/Filmmagic
05of 08NICOLE RICHIEKevin Mazur/WireimageRichieand 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 theSimple Lifestar 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.”
05of 08
NICOLE RICHIE
Kevin Mazur/Wireimage
Richieand 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 theSimple Lifestar 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.”
06of 08PARIS HILTONEric Boone/Splash News OnlineDid Jenner enjoy 1 Night with Paris? The world may never know. In 2008, he was photographed getting close with hisex’s frenemyin Sin City on New Year’s Eve. That’s hot. Theylooklike 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.
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PARIS HILTON
Eric Boone/Splash News Online
Did Jenner enjoy 1 Night with Paris? The world may never know. In 2008, he was photographed getting close with hisex’s frenemyin Sin City on New Year’s Eve. That’s hot. Theylooklike 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.
07of 08HAYLIE DUFFZavar Manokian/BuzzfotoAnother mystery match: Duff and Jenner were seen partying together in West Hollywood in 2007, and an onlooker called them “inseparable.” Little sisterHilary Dufftried 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.”
07of 08
HAYLIE DUFF
Zavar Manokian/Buzzfoto
Another mystery match: Duff and Jenner were seen partying together in West Hollywood in 2007, and an onlooker called them “inseparable.” Little sisterHilary Dufftried 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.”
08of 08LEAH JENNERImeh Akpanudosen/Getty; Chelsea Lauren/WireimageYes, you read that right:Leahis happily married toBrandonJenner 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.
08of 08
LEAH JENNER
Imeh Akpanudosen/Getty; Chelsea Lauren/Wireimage
Yes, you read that right:Leahis happily married toBrandonJenner 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.
source: people.com
