Kardashian-Jenner Romances Through The Years: Photos

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December 21, 2018 5:23PM EST

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Kardashian-Jenner Romances Through The Years

Kardashian-Jenner Romances Through The Years — The Kardashian-Jenner women can’t hide a romance even if they tried. Hollywood’s most famous family can’t escape sleuthing fans, paparazzi and the internet when it comes to trying to keep every detail of their lives private. From rappers to athletes, entrepreneurs and everyone in between, Khloe, Kim, Kourtney, Kylie and Kendall have had a number of juicy hookups, surprising flings and serious romances with some familiar faces. Kim married Kris Humphries and filed for divorce all in a 72-day span; Khloe said ‘I do’ with Lamar Odom just 30 days after they met; Kylie kept her pregnancy with Travis Scott a secret until she gave birth; Kourtney would hit the club and church with her past fling Justin Bieber, while dating other younger men; And, Kendall’s just living her best life dating whoever she wants, because she can. Take a look through our attached gallery to get a recap on each of the sisters’ past and present relationships.

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Kendall Jenner & Devin Booker

Kendall Jenner & Devin Booker — Kendall Jenner and Devin Booker appear to be going strong as they are spotted enjoying a romantic date night out in West Hollywood on October 3, 2020. The two were a hot item during the summer, and fans can’t get enough of their flirty, close relationship!

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Kylie Jenner & Travis Scott

Kylie Jenner & Travis Scott — Kylie Jenner and Travis Scott coordinated in black ensembles on the red carpet at the Met Gala in New York, NY, on May 7, 2018. They first sparked romance rumors after being spotted together at a Coachella party in April 2017.

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Tyga & Kylie Jenner

Tyga & Kylie Jenner — Tyga and Kylie Jenner posed on the red carpet at the annual Harper’s Bazaar ICONS party at New York Fashion Week on September 9, 2016. Tyga was Kylie’s most serious and longest relationship before she moved on with Travis Scott. Kylie was very serious with T-Raww from 2014-2017. He attended family vacations and parties and was even featured on ‘KUWTK.’

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Kim Kardashian & Kanye West

Kim Kardashian & Kanye West — Here, Kim Kardashian and Kanye West are together on the red carpet at the Vanity Fair Oscars Party in LA, following the awards show. The now parents of four were friends for many years before they got together. Kimye were spotted for the first time together in April 2012, confirming rumors that they were dating. By that December, they were expecting their first child together. They got engaged in October 2013 and wed in Italy the next May.

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Kim Kardashian & Kris Humphries

Kim Kardashian & Kris Humphries — The two were first spotted together in October 2010, got engaged in May 2011, and said ‘I do’ a few months later in August. Kim and Kris split 72 days after their wedding. Their divorce was finalized in June 2013.

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Kim Kardashian & Reggie Bush

Kim Kardashian & Reggie Bush — Kim Kardashian dated the NFL player on and off from 2007 to 2010. Their relationship was partly shown on episodes of ‘Keeping Up With the Kardashians.’

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Kim Kardashian & Ray J

Kim Kardashian & Ray J — Their relationship was cast into the public eye after their now infamous sex tape leaked in 2007. Kim and the singer were on vacation in Cabo for her 23rd birthday when they filmed the tape, that was initially not supposed to get out. They dated from 2005 to 2007.

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Lamar Odom & Khloe Kardashian

Lamar Odom & Khloe Kardashian — These two wed in September 2009 after just one month after they met. Khloe filed for divorce in December 2013, while Lamar was struggling with drug and alcohol abuse. She also claimed he had cheated on her. Their divorce wasn’t finalized until December 2016 because Khloe held it off to be Lamar’s primary caretaker after he suffered a drug overdose in October 2015.

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Khloe Kardashian and Tristan Thompson

Khloe Kardashian and Tristan Thompson — Khloe Kardashian and the NBA player held hands while out on a sunny afternoon in LA. Khloe and Tristan first started dating in August 2016 and broke up in April 2018, after Tristan was caught cheating on Khloe just two days after she gave birth to their daughter True Thompson on April 12.

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Khloe Kardashian & James Harden

Khloe Kardashian & James Harden — Khloe Kardashian and James Harden were spotted leaving The Nice Guy in West Hollywood after Kylie Jenner’s 18th birthday party on August 9, 2015. They had a brief fling that summer before things just ran their course.

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Khloe Kardashian & French Montana

Khloe Kardashian & French Montana — Khloe Kardashian and French Montana reunited at a mutual friend’s birthday party at BOA Steakhouse on February 8, 2016. Khloe and French, who is a close friend of the Kardashian family, dated on and off casually for months in 2014. However, they remained close friends when their romance fizzled out.

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Scott Disick & Kourtney Kardashian

Scott Disick & Kourtney Kardashian — Scott is the only Kardashian-Jenner man to have a regular role on their E! series, ‘KUWTK.’ He is the father of Kourtney’s three kids, and gets along well with his ex and the family. Kris Jenner has also made it known that Scott will always be part of the family, vacations and parties included. Kourtney and Scott dated for a decade before they called it quits in 2015.

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Younes Bendjima & Kourtney Kardashian

Younes Bendjima & Kourtney Kardashian — Younes was Kourtney’s first serious boyfriend after her split from longtime boyfriend. The two were on-again and off-again, but seemed to be on good terms or back together in Decemebr 2019 after they were spotted in Disneyland together. Younes also attended the Kardashian Christmas Party weeks later.

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Kourtney Kardashian & Justin Bieber

Kourtney Kardashian & Justin Bieber — The pair, who’ve been close friends for years, had a brief hookup/fling around the end of 2015. They were seen hanging out together at various clubs throughout December, folowing her split from longtime boyfriend Scott Disick. Nothing ever turned serious between the two.

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Kendall Jenner & Ben Simmons

Kendall Jenner & Ben Simmons — Kendall Jenner and Ben Simmons were pictured heading to the beach during their couples getaway to Mexico with her sister Khloe Kardashian and then boyfriend, Tristan Thompson in August 2018. Kendall and Ben began dating in the summer of 2018 and broke up a year later. However, that wasn’t the end. The two reinkindled their romance in January 2020 after being spotted in New York City together.

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Kendall Jenner & Blake Griffin

Kendall Jenner & Blake Griffin — Kendall Jenner and NBA player Blake Griffin enjoyed a dinner at Ocean Prime restaurant in Beverly Hills with Blake’s buddies Chandler Parsons, NBA Exec James Dunleavy and film producer Michael D. Ratner on October 11, 2017. Kendall and Blake first got together in September 2017, shortly after the he ended his engagement to Brynn Cameron, with whom he shares two children. They split less than one year later. And, she moved on with Sixers point guard, Ben Simmons.

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Kendall Jenner & ASAP Rocky

Kendall Jenner & ASAP Rocky — ASAP Rocky and Kendall Jenner showed off some PDA at the Met Gala in New York, NY on May 1, 2017. The pair dated from 2016 to 2017 and broke up because of their difficult schedules.

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Harry Styles & Kendall Jenner

Harry Styles & Kendall Jenner — Harry Styles and Kendall Jenner ran into each other at the British Fashion Awards in London on December 1, 2014. The photo was taken after their split. Kendall and Harry dated from late 2013 until early 2014, and remained friends after they split.

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Kendall Jenner & Anwar Hadid

Kendall Jenner & Anwar Hadid — Kendall Jenner and Anwar were spotted leaving Cipriani after a night of partying in New York City. The supermodel and Gigi Hadid’s little brother had a playful fling in November/late 2018, but never seriously dated.

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