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Kardashian-Jenner Romances Through The Years: Photos

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Kardashian-Jenner Romances Through The Years

Kardashian-Jenner Romances Through The Years
Shutterstock

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.  

March 25, 2020, 12:51PM
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Kendall Jenner & Devin Booker

Kendall Jenner & Devin Booker
BACKGRID

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!

January 6, 2021, 11:34AM
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Kylie Jenner & Travis Scott

Kylie Jenner & Travis Scott
Broadimage/Shutterstock

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.

January 31, 2020, 9:56AM
4 of 20

Tyga & Kylie Jenner

Tyga & Kylie Jenner
Kristina Bumphrey/Starpix/Shutte

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.’ 

March 25, 2020, 12:17PM
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Kim Kardashian & Kanye West

Kim Kardashian & Kanye West
Matt Baron/Shutterstock

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. 

March 25, 2020, 12:21PM

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6 of 20

Kim Kardashian & Kris Humphries

Kim Kardashian & Kris Humphries
Shutterstock

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. 

March 25, 2020, 12:21PM
7 of 20

Kim Kardashian & Reggie Bush

Kim Kardashian & Reggie Bush
Bei/Shutterstock

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.’

March 25, 2020, 12:23PM
8 of 20

Kim Kardashian & Ray J

Kim Kardashian & Ray J
Shutterstock

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. 

March 25, 2020, 12:46PM
9 of 20

Lamar Odom & Khloe Kardashian

Lamar Odom & Khloe Kardashian
Jim Smeal/BEI/Shutterstock

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. 

March 25, 2020, 12:24PM
10 of 20

Khloe Kardashian and Tristan Thompson

Khloe Kardashian and Tristan Thompson
BAHE / BACKGRID

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. 

December 21, 2018, 4:13PM
11 of 20

Khloe Kardashian & James Harden

Khloe Kardashian & James Harden
Maciel / AKM-GSI

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.   

March 25, 2020, 12:27PM
12 of 20

Khloe Kardashian & French Montana

Khloe Kardashian & French Montana
DEBY / AKM-GSI

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. 

March 25, 2020, 12:30PM
13 of 20

Scott Disick & Kourtney Kardashian

Scott Disick & Kourtney Kardashian
Mediapunch/Shutterstock

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. 

March 25, 2020, 12:37PM
14 of 20

Younes Bendjima & Kourtney Kardashian

Younes Bendjima & Kourtney Kardashian
Mediapunch/Shutterstock

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. 

March 25, 2020, 12:39PM
15 of 20

Kourtney Kardashian & Justin Bieber

Kourtney Kardashian & Justin Bieber
SplashNews.com

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. 

March 25, 2020, 12:37PM
16 of 20

Kendall Jenner & Ben Simmons

Kendall Jenner & Ben Simmons
Maciel / NGRE / BACKGRID

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. 

December 21, 2018, 4:13PM
17 of 20

Kendall Jenner & Blake Griffin

Kendall Jenner & Blake Griffin
Maciel / NGRE / BACKGRID

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. 

March 25, 2020, 12:16PM
18 of 20

Kendall Jenner & ASAP Rocky

Kendall Jenner & ASAP Rocky
Taylor Jewell/Vogue/Shutterstock

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.

March 25, 2020, 12:16PM
19 of 20

Harry Styles & Kendall Jenner

Harry Styles & Kendall Jenner
Nick Harvey/Shutterstock

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. 

March 25, 2020, 12:16PM
20 of 20

Kendall Jenner & Anwar Hadid

Kendall Jenner & Anwar Hadid
BlayzenPhotos / BACKGRID

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. 

 

December 21, 2018, 4:13PM
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