I’m sure we’re all familiar with the Kardashians and the Jenner sisters. They’re well known due to their wealth, TV shows, modelling and Kylie’s cosmetic industry. Because of their eventful lifestyle, we wouldn’t expect less than an eventful love life, as well! However, even though the sisters’ love life is constantly a talking point, we might have missed or forgot some of the guys that the sisters dated through the years. Make sure not to miss #18, #16 and #15!

20. T.J. Jackson And Kim

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Michael Jackson’s brother, T.J, started dating Kim in High School. Kim and T.J, grew up together in the same neighbourhood as friends. However, their friendship turned into something more in 1994. That was the year when both of them announced that they were together. They dated for about four years and he might was Kim’s first boyfriend. The next guy that one of the sisters dated will blow your mind!

19. Justin Bieber And Kourtney

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Now who remembers that these two were dating? Well, when Justin was only 21, he and Kourtney used to hang out a lot. So, many believed that there was something romantic between them. However, the rumors didn’t last long, because after some time, they distant themselves from each other. Click next to learn who Kendall’s secret boyfriend was!

18. Anwar Hadid And Kendall

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Yes! Anwar Hadid is Gigi’s and Bella’s little brother! The rumors for those to dating, began in June 2018, when they were seen kissing each other at an after-party in New York. Even though they broke up in September 2018, the most interesting thing is that in June 2018, Kendall was supposedly with Ben Simmons!

17. Joey Lawrence And Kim

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Joey Lawrence is a musician, a host at game shows and an actor. The rumors of him dating Kim started back in 1999. However, their relationship didn’t last for long as they broke up pretty soon after their announcement of being together.

16. Ray-J And Kim

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After breaking up with her former husband and music producer Damon Thomas in 2004, Kim started dating Ray-j. Even though their relationship lasted about three years, we’re sure that the tape of her that leaked in February 2007 didn’t make it easy to forget this relationship!

15. Nick Lachey And Kim

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Even though the rumors of the two of them being in a relationship were never confirmed, they had spotted many times hanging out together and holding hands. All of that took place in 2006, when both of them had recently broken up with their former partners.

14. Rashad McCants and Khloe

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These two started dating in 2009, while Khloe had her own TV show with her sister, Kourtney, named “Kourtney and Khloe take Miami”. In one of the episodes, Khloe claimed that Rashad was having an affair with another woman. However, after they broke up and the end of the show, Rashad admitted that he never cheated on her, but it was all made up for the sake of the show.

13. Harry Styles And Kendall

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Even though that the two of them dating was never confirmed, they had been spotted together many times through the years 2013-2016. They used to hang out, to go for romantic dinners and organizing yacht trips. So, the facts speak for themselves!

12. Derrick Ward And Khloe

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Those two started dating, no long after Khloe broke up with her former partner, Rashad McCants in 2009. The football player Derrick Ward and Khloe had seen enjoing each other’s company down in Mexico, to where all of her family had organized a trip for Kourtney’s 30th birthday.

11. Matt Kemp And Khloe

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After dating Derrick Ward and Rashad McCants, Khloe, got married, after only one month of dating, with Lamar Oden. However, after three years, they took a divorce. No long after that, Khloe was seen in a Drake’s concert in December 2013 hanging out with baseball star Matt Kemp.

10. French Montana And Khloe

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Even though the two of them seemed not to get along so well, their on and off relationship lasted about a year, until they broke up permanently. “I jumped into something because I was just, like, lonely and destructive, but now I’m like, I just want to be alone,” she said in one episode of her show.

9. Rick Fox And Khloe

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No long after splitting up with the rapper French Montana, Khloe started a relationship with Rick Fox, a retired NBA player. They were spotted in May 2015 in Mexico, where they were enjoying each others company at a bar.

8. Younes Bendjima And Kourtney

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Even though the first public announcement of their relationship took place in May 2017, Kourtney admitted that they actually started dating in October 2016. Since then, the couple has been seen hanging out together and having a great time. However, even though none of them has admitted it, it’s obvious that they have broken up, since Bendjima has been spotted in Mexico with Jordan Ozuna.

7. Joe Francis And Kourtney

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It’s not clear if these two were truly dating. Supposedly, they started dating in 2005 and their relationship lasted for seven months. However, it seems that Joe was the one that hooked Kourtney up with Scott Disick. “I introduced Kourtney and Scott at my house in Mexico. Scott came as the guest of a friend of mine, and they met in my master bedroom,” Joe said in an interview.

6. Taryll Jackson And Kourtney

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Even though T.J Jackson was Kim’s first love back in 1998, The Jackson family charmed another Kardashian. Taryll is T.J’s older brother and started a relationship with Kourtney back in 2001. Their relationship lasted for about four years.

5. Ben Simmons And Kendall

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After breaking up with Blake Griffin, Kendall started shortly after dating Ben Simmons, a NBA star. Simons and Kendall were spotted together for the first time in May 2018. However, their relationship lasted only four months and they were seen together for the last time in August 2018.

4. Julian Brooks And Kendall

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There are not much information about the relationship of Julian Brooks and Kendall. All that is known is that they were high school sweethearts and that they started dating in 2012. Their relationship lasted a year.

3. Cody Simpson And Kylie

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The two supposedly started dating back in 2011. However, we do not know for how long Cody Simpson and Kylie were dating until they chose different paths. “No, the whole K-O-D-Y thing didn’t really work for me,” Cody said in an interview.

2. Jaden Smith And Kylie

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Son of the famous actor Will Smith, Jaden Smith was linked romantically with Kylie back in March 2013. Although they seemed to getting along pretty good, they broke up a bit later, the same year. Regardless their past, the two of them are still good friends.

1. Miles Richie And Kylie

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Miles Richie, the son of Lionel Richie, the music legend, supposedly started having a relationship with Kylie during the summer of 2014. They were spotted hanging out, going for car rides and having a great time. Miles Richie also tattooed her initials on his hand!