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Everyone Kardashian/Jenner’s Have Dated

The Kardashians are some of the most famous celebrities on the face of the planet currently. That’s just the way it is. Not a day goes by without some exciting news about one member of the fam. It could be a not-so-surprising baby announcement, a Twitter feud, or even new info about their love lives that gets social media stirring. There’s almost too much to keep up with! With a new scandal happening to one of the Kardashian-Jenners on a daily basis, we tend to forget certain scandals – and romances – from years’ past.

Before their current significant others like Kanye West or Tristan Thompson, the Kardashian-Jenner family had some ~*interesting*~ past flings and, surprisingly, even some marriages that you maybe didn’t know about. If you’re a fan of this famous fam, you’re probably in the know about exes like Kris Humphries and Blac Chyna, but that doesn’t mean you’ve got every single one on lock. Keep scrolling to see all the Kardashian-Jenner lovers of the past that you just may have forgotten about.

19. Reggie Bush

Before Kanye West entered the picture as Kim Kardashian‘s main man, she was in a relationship with football player Reggie Bush for quite some time. As some avid Keeping Up With the Kardashians viewers know, the athlete made frequent appearances on the earlier seasons of the show as Kim’s beau. The two started dating in 2007, briefly broke up and got back together in 2009, but then eventually called things off for good in 2010.

It didn’t seem like there was too much bad blood in the couple’s split. They supposedly parted ways due to some normal relationship issues like whether they were ready for marriage. Ever since their split, Kim’s found happiness with Yeezy and Reggie married Lilit Avagyan in 2014.

18. Nick Lachey

Can you even believe that once upon a time, Nick Lachey and Kim Kardashian were kind of an item? Apparently, the two only dated for about a week in 2006, long before Kim became the uber famous star she is today. So, that’s probably why you didn’t know this super random celebrity fact.

Lachey told Details that he believes this brief relationship partly helped the reality star become famous. Um… okay, Nick Lachey. He implied in his interview with the magazine that Kim called the paparazzi to photograph them when they went out on a movie date. We’re calling his bluff on this one. It’s highly unlikely that Kim Kardashian is one of the most famous people in the world (if not THE most famous person in the world) because of paparazzi taking photos of her with a C-list former boy bander a decade ago. Lol.

17. James Harden

James Harden definitely gets lost in the shuffle of Khloé Kardashian‘s exes. Still, the two dated for about a year from 2015 to 2016, and they seemed to be a strong couple at the time. He even managed to be a good support system for Khloé when her ex-husband, Lamar Odom, experienced an overdose.

However, their relationship didn’t last long. When he looked back on the relationship to Sports Illustrated, Harden described the year that they dated as one of the worst of his life. He said that he “didn’t like all the attention” he received when he was dating the Kardashian sibling. Well, that’s exactly what you’re in store for when you date a member of the most famous family in Hollywood.

16. Ray J

Okay, so everyone probably knows all about that sex tape. But, Ray J and Kim Kardashian’s relationship is probably a total afterthought to all of that craziness. The two originally met after Kim worked as a personal stylist for Ray J’s sister Brandy, a popular singer at the time. It’s unclear exactly when the two started dating, but it was sometime in 2005 and the pair was broken up by the end of 2006. Some early reports state they started hooking up in 2003 – but it was pr-Kardashian uber-fame, and therefore, pretty hard to prove since neither party really takes time to relive the good ol’ days now.

Of course, around the same time they broke up, that now-famous Kim Kardashian sex tape was released.

15. Cody Simpson

Long before the days of Tyga and Travis Scott, Kylie Jenner had a brief relationship with singer Cody Simpson. The young pair dated in 2011 but weren’t very open about their relationship status. They didn’t last long as a couple, though. Simpson later joked in 2014 that the two didn’t see eye-to-eye, at least in terms of initials. He said, on Hello Ross, “The whole K-O-D-Y thing didn’t really work for me.”

Regardless of that silly difference of opinion, the just weren’t meant to be. And seeing as though the two were both super young when they dated, they were both around 14 years old at the time, it’s not really a surprise that the two eventually broke up. It’s a small world, though, because Cody went on to date Gigi Hadid, with whom big sister, Kendall Jenner is tight with now.

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14. Damon Thomas

Some people may not know that before Kanye West, and before Kris Humphries, Kim Kardashian was indeed married and the nuptials weren’t exactly brief. Kim’s first marriage was to music producer Damon Thomas, whom she was married to from 2000 to 2004. The pair eloped when the reality star was only 19 years old. The two officially divorced in 2004 after citing “irreconcilable differences” for their split. According to the Daily Mail, court records that were unearthed in 2011 revealed that Kim alleged that Thomas was emotionally and physically abusive towards her during their marriage, claims which he denied.

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Ever since she separated from Thomas, Kim’s shot to worldwide fame, become a successful businesswoman and found a strong partner in Kanye. So, she’s definitely doing well for herself and no one knows who Damon Thomas is anyways!

13. Terrence Jenkins

Anyone remember Kourtney and Khloé Take Miami? The fun Keeping Up With the Kardashians spin-off saw the sisters opening a new Dash store in the Florida area. During the show, Khloé also took on hosting duties for a Miami-based radio show, where she discussed a variety of topics with her co-host, Terrence Jenkins (a.k.a. Terrence J). What some people may have forgotten is that there was a little something going on between the two of them. While it wasn’t a confirmed full-fledged relationship – the two did share a steamy makeout sesh in a club on the show. Terrence is now the host of MTV’s Are You The One? and regularly chills with Michael B. Jordan, so we’re going to say he’s doing pretty well for himself.

12. Miles Austin

In terms of Kim Kardashian’s brief relationship with Miles Austin, it would be surprising if you didn’t forget about it. Kim was on the rebound after her breakup with Reggie Bush when she started dating this football player Austin in 2010. Their blossoming romance was even captured on Keeping Up With the Kardashians, where the two had a fun Fourth of July date.

However, these two weren’t meant to last. Their breakup, which also came in 2010, seemed amicable enough. Apparently, the two broke up because it was hard to keep up with their long-distance relationship and balance their work commitments (Kim lived in California and Miles was in Dallas playing for the Cowboys). Fair enough!

11. Adrienne Bailon

Way back when Keeping Up With the Kardashians first started, Rob Kardashian was going strong with his girlfriend, former Cheetah Girl Adrienne Bailon. The two did have their cute moments on the show and Bailon seemingly got on well with all of Rob’s sisters. But, things weren’t always so good with the twosome, who dated from 2007 to 2009.

Rob himself revealed on KUWTK that he had cheated on his girlfriend of two years, which obviously led to the pair’s split. Bailon later said, in 2017, that her breakup buddy at the time was none other than Rob’s sister Kourtney Kardashian. According to E! News, Kourtney had just broken up with Scott Disick around the same time, and the two gals leaned on each other during the difficult period. In 2014, however, Adrienne bashed the Kardashians during an interview with Latina magazine and there have been rough waters between the singer and the famous family ever since.

10. Nick Cannon

Yep, Kim Kardashian has also dated another famous “Nick,” Nick Cannon. The couple didn’t date for very long, though. Kim and Cannon started dating around September of 2006 and broke up in early 2007. So, it’s not like they were soulmates or anything.

Cannon said on The Howard Stern Show that they broke up because Kim apparently lied to him about the existence of her sex tape. Regardless of whether that’s the real reason for their break up or not, it seems like there are no hard feelings between them, at least on his end. When he appeared on Power 106, he said that Kim and the rest of her family are great people. Good on them for a seemingly mature post-breakup relationship. Guess when you don’t date for too long that’s not too hard.

9. Rita Ora

Rob Kardashian and singer Rita Ora had a turbulent relationship, to say the least. The two had a brief fling in 2012, but things got pretty messy between them very quickly. In December of 2012, the two were headed to splitsville and some nasty tweets from Rob sealed the deal. He tweeted (then deleted, naturally) that the two were over because Ora allegedly cheated on him with multiple people. “She cheated on me with nearly 20 dudes while we were together,” he wrote. “But I mean 20?!!!!… I am actually disgusted.” Thank god for screenshots.

Rita tweeted in her side of the story saying, “Rob’s dick was wack, I had to go get it somewhere else.” LOL. Later, in an interview, she also said that she “never thought it was a relationship.” Well, that’s awkward for Rob. As we already know from his relationship fallout with Blac Chyna, the Kardashian bro has a penchant for poor social media conduct and slut-shaming, so his outburst wasn’t super surprising – just disappointing.

8. Harry Styles

Kendall Jenner and this One Direction cutie’s relationship was like a match made in beautiful pop culture heaven. The two young stars supposedly had a somewhat serious relationship on-and-off for a couple of years from 2013 to 2016. Since the pair was always kind of secretive about their relationship status, it’s unclear when exactly the relationship began and ended (her sister, Khloé Kardashian, did sort of confirm that they were dating in 2016, though). There were also pictures leaked of the two of them hanging on yacht when Harry’s mom’s iCloud account got hacked. It was juicy, but that’s a pretty low move.

It’s probably a good thing that these two broke up, honestly. Styles has been connected, at various points in time, with numerous friends of Kendall’s, like Cara Delevingne and Taylor Swift. Talk about awkward!

7. French Montana

French Montana was basically Khloé Kardashian’s rebound relationship when the pair first started dating in 2014 hot off of her separation Lamar Odom. They were dating during the filming of Kourtney and Khloé Take The Hamptons and their relationship actually seemed pretty sweet. But it didn’t last and they broke up in 2015. The youngest Kardashian sister even revealed later on that she wasn’t quite ready for that serious of a relationship right after her breakup with her husband. There’s no bad blood between the pair at all, though. They’ve seemingly stayed friendly with each other since their split and French Montana even appeared on a recent episode of Keeping Up With the Kardashians in 2017 (as a friend).

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6. A$AP Rocky

Kendall Jenner and A$AP Rocky’s relationship was a recent one but, they kind of flew under the radar because the pair actually never revealed whether they were an official item or not. They were photographed out together numerous times on dinner (and shopping) dates starting in 2016, and A$AP’s mom pretty much confirmed they were together when she publicly slammed the Kardashian-Jenner clan. “Everything I hear about the Kardashians makes me think they are a bad family for Rakim to be involved with. I don’t want him being dragged into that circus, he is too good for that and can do so much better,” she said. Oh, boy. They’re not together anymore, but we wouldn’t even know it if it weren’t for KJ’s new flame, Blake Griffin‘s ex’s not-so-nice words about their new fling in court documents.

5. PartyNextDoor

It’s likely that you don’t remember that Kylie Jenner once dated rapper PartyNextDoor because their relationship didn’t exactly last too long considering it was wedged in between one of Kylie and Tyga‘s many breakups. In the spring of 2016, the youngest Kardashian-Jenner sibling found herself in the arms of PND, quite literally, while they were filming his music video for “Come and See Me.” Kylie was back with Tyga by that August, proving that no one can get in between that crazy couple. Oh, wait…

4. Rashad McCants

Khloé Kardashian dated NBA player Rashad McCants briefly in 2009. This duo was together for a little while during Kourtney and Khloé Take Miami and their relationship drama played out fully on the show. While filming that season of the spin-off show, the Revenge Body star allegedly found out that McCants had been cheating on the star when she and Kourtney hacked into his voicemails and found some suggestive messages from a fan. It was all kinds of wild.

McCants denied the cheating claims and even claimed that the whole scandal was made up for the sake of the show. But, the damage was done with these two. Plus, it’s not like they were anything too serious anyway.

3. Jaden Smith

Kylie Jenner’s relationship with Jaden Smith was never exactly official, but it may as well have been. The pair was romantically linked in 2014 and they were spotted kissing at Kim Kardashian and Kanye West’s wedding that year, according to reports from E! News.

Regardless of whether the two were officially an item at the time, they’ve remained good friends in the years since. That’s pretty surprising considering this relationship hasn’t been without its fair share of some dramz, as is the Kardashian-Jenner way. In early 2017, Hollywood Life reported that Jaden’s ex-girlfriend Sarah Snyder and Kylie got into an Instagram feud where they traded subtle digs with one another – though the reason is unclear and Jaden apparently wanted none of it.

2. Ben Flajnik

You might never even guess which member of the Kardashian-Jenner family dated Ben Flajnik a.k.a. the former lead of The Bachelor. In 2014, it was rumored that Flajnik had a fling with none other than the family matriarch herself, Kris Jenner. Yes, we had to include the most famous mom-ager of all time on this list!

We all know Kris has a penchant for younger guys, and when the two were spotted together on numerous occasions, gossip started pouring in saying that this odd-couple was definitely hooking up. Some sources admitted that Ben was just looking for fame, but he was almost certainly edited out of quite a few episodes of KUWTK during the time when they were hanging out regularly. However, both Kris and Flajnik later insisted that they weren’t dating and were just good friends. We’re unconvinced but who knows?!

1. Justin Bieber

Now, Justin Bieber’s an interesting item on this list because he’s been linked to not one, not two, but THREE of the Kardashian-Jenner sisters. How unbelievable is that! None of them have been **confirmed** on any official level, but there’s certainly something sketchy going on here! The Biebs has been rumored to be dating Kendall, Kylie, and Kourtney throughout the years. There has even been speculation about Kim K. and JB hooking up, but there’s even less evidence for that one than the other three pairings.

JB was tied to Kourtney following her 2015 breakup from Scott Disick. He’s actually only one year younger than her current beau, Younes Bendjima so this one’s not too far-fetched. That said, he was only 20 years old when this fling allegedly went down and Kourt was 35.

Meanwhile, Kylie and the “Sorry” singer were rumored hooking up just a year before that – around the same time she was apparently with Jaden Smith. What’s even JUCIER is that he was rumored to be with Kendall at the same time as Kylie. The most likely explanation is that he was actually only hooking up with one of them – and our money’s on the older Jenner sis. Several cozy pictures were leaked of the two all over each other. Also, JB said things with Kendall were “never serious”… but that’s basically a confirmation they were casually dating, right? It’s unclear. For all we know, Bieber could just be a good family friend. Still, it’s kind of wild to think that he’s a thrice-over Kardashian-Jenner ex-boyfriend – even twice over would be absolutely crazy.

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