KUWTK: A Look At Kim’s Dating History Throughout The Years

After six years of marriage, Kim Kardashian and Kanye West are calling it quits. Although the divorce papers have yet to be signed as of this writing, fans of “Keeping Up With The Kardashians” are wondering about who could be Kardashian’s next suitor. Many are hopeful that the reality star will end up with CNN commentator Van Jones, who has become the center of dating rumors. The two have previously collaborated together on prison reform initiatives. 

For now, it seems as if Kardashian is just enjoying her life as a single woman. “Kim isn’t ready to date and is not focused on dating yet,” a source told E! News in February 2021. “She’s had a rough year and wants to focus on herself and her kids right now.” Despite the hardships of divorce, Kardashian seems to have a different perspective on her love life compared to her previous relationships. Let’s take a trip down memory lane of Kim Kardashian’s dating history since being thrust into the spotlight.

Kim Kardashian eloped with Damon Thomas

At the age of 19, Kim Kardashian left her shop assistant job and eloped with Damon Thomas — a music producer best known for his work with The Underdogs production group. Alongside Harvey Mason Jr., Thomas has worked with high profile artists such as Pink, Faith Evans and Chris Brown. Additionally, he’s helped with producing films, such as “Dreamgirls.” Kardashian and Thomas married in Las Vegas in January 2000. According to the reality star, things did not end well between them. “He did not want me to have contact with my old boyfriends, who would be able to reach me at the clothing store,” Kardashian claimed in her 2003 divorce proceedings, which were finalized in 2004. “He said he wanted to know where I was at all times.”

In 2018, Kardashian revealed she was high on ecstasy when she married Thomas. “I did ecstasy once, I got married,” she told Kendall Jenner and Scott Disick during an episode of “Keeping Up With The Kardashians” (via Page Six). “I did it again, I made a sex tape.” Since then, Kardashian maintains her sobriety, as she only drinks alcohol occasionally.

Kim Kardashian and Ray J's relationship ended in scandal

Obviously, there’s no happy ending for this one. Kim Kardashian and Ray J’s relationship did not end amicably. Kim Kardashian and Ray J reportedly met while the former worked as a closet organizer and stylist for his older sister, singer Brandy, in 2005. According to Ray, the two allegedly began a sexual relationship before Kardashian’s divorce from Damon Thomas. In his confessional book, “Death of a Cheating Man: What Every Woman Must Know About Men Who Stray,” Ray revealed details about his relationship with a woman he refers to as “KK,” which isn’t far off from Kardashian’s initials (insert sarcasm here).

“To be honest, the whole thing started off wrong. We’d known each other for a while before we dated and there was a mutual attraction, but she was married,” Ray wrote. “She let me know she wanted to get with me. She left her husband for me as soon as we started having sex and things between us got intense really fast. After that, I felt obligated to be with her.” The “One Wish” singer revealed he and KK cheated on one another and their relationship fell apart from KK’s jealousy.

We all know what happens next: In 2007, Kardashian and Ray J’s sex tape surfaced on the internet by porn company Vivid Entertainment. Although unfortunate, Kardashian’s career skyrocketed from that infamous moment. In 2018, Kardashian admitted to being high on ecstasy at the time. She has since called the “I Hit It First” crooner a “pathological liar.” Yikes.

Nick Lachey says Kim Kardashian isn't necessarily his ex

Even before her sex tape and the reality TV fame, Kim Kardashian was already gaining attention from her friendship with Paris Hilton. Additionally, Kardashian was the first girl Nick Lachey was spotted on a date with following his split from Jessica Simpson in 2006. Lachey, however, does not consider Kardashian to be his ex, as he clarified that referring to her as such “is a little bit of a liberal use of the term.”During an episode of “Watch What Happens Live with Andy Cohen,” Lachey recalled the date with Kardashian. He revealed the two went to a matinee showing of “The Da Vinci Code.”

“She left about halfway through and went to the restroom, and then shockingly, there were 25 paparazzi when we left the theater,” said the 98 Degrees singer. “I think there were other things in play on our little rendezvous.” Although the date went well, nothing seemed to get off the ground from there. “Couldn’t be a nicer girl, we had a great time,” Lachey continued. “But no, we don’t keep in touch anymore.”

Kim Kardashian and Nick Cannon ultimately ended due to her infamy

Nick Cannon and Kim Kardashian were briefly an item. The two dated from September 2006 to January 2007, per Showbiz Cheat Sheet. The two split just before she became an international superstar with her family’s show, “Keeping Up With the Kardashians.” Unfortunately, things ended between Kardashian and Cannon after the latter learned that she lied to him about the existence of her sex tape with Ray J. Cannon told Howard Stern that if Kardashian “had been honest” with him, he likely wouldn’t have broken up with her “because she is a great girl.” Calling Kardashian a “great businesswoman,” he also suggested that Kardashian may have leaked her own tape.

“She’s actually one of the nicest people you’ll ever meet,” Cannon explained (via HuffPost). “But the fact that she lied and told me that there was no tape? And I still think she might have even had a part to play with [its release].”

Their relationship also ended poorly, as they reportedly ignored one another at a fashion event in 2007.

Kim Kardashian and Reggie Bush's schedules clashed while in a relationship

One of Kim’s notable relationships is with NFL athlete Reggie Bush. Kardashian and Bush dated between the years of 2007 to 2010. The former lovers met at the 2007 ESPY Awards after being introduced by a mutual friend. It wasn’t long before the two began dating, and viewers got to see the budding romance grow on “Keeping Up With The Kardashians.” The pair became the hottest couple in Hollywood, given their high-profile status.

Like any other couple, Kardashian and Bush had challenges in their relationship. Due to their conflicting schedules, the couple briefly split in 2009 to focus on their respective careers. “They love each other a lot and hope someday they can make it work,” an insider told E! News at the time. “But for now, he starts his football season this week and Kim starts filming season four of “Keeping Up With the Kardashians,” and they just need this time apart.” The couple reconciled in 2010, but later split in 2010.

There is no clear indication why they broke up. However, Kanye West’s ex, Amber Rose, claimed that Kardashian cheated on Bush with West. In a 2012 interview with Star Magazine (via Page Six), Rose explained, “Kim is one of the main reasons why me and Kanye are not together. She’s a homewrecker.”

Rose added, “They were both cheating on me and Reggie with each other.” 

Bush and Kardashian have since found love elsewhere. Bush’s wife, Armenian dancer Lilit Avagyan, is said to be Kardashian’s doppelgänger, as well as their daughter. Clearly, Bush as a type.

Kim Kardashian and Cristiano Ronaldo were cozied up on vacation

In April 2010, Kim Kardashian had everybody talking when she was said to be hooking up with heartthrob soccer player, Cristiano Ronaldo. Ronaldo is also the ex of Kardashian’s former friend, Paris Hilton. Kardashian and Ronaldo reportedly met at an event at the Beverly Hills Hotel. Per Daily Mail, she was spotted canoodling with Ronaldo during a vacation in Madrid. Additionally, the pair reportedly had a romantic dinner while Kardashian, who was freshly broken up from Reggie Bush at the time, was on vacation. The two were spotted leaving dinner in separate cars back to the soccer star’s gated community. “She and Ronaldo were kissing and very affectionate,” a source told the publication. “They looked to be getting on really well, laughing the whole time.”

The two briefly had a relationship, but it was nothing serious at the time. By August 2010, Ronaldo moved on to Irina Shayk. Of course, Kardashian has since moved on from the short fling with the athlete.

Miles Austin and Kim Kardashian couldn't keep up with each other

After being romantically linked to Cristiano Ronaldo, Kim Kardashian began dating Dallas Cowboys player Miles Austin in the summer of 2010, according to Us Weekly. The two dated for a few short months, and their relationship was described by a source to be “stronger than ever,” according to People. Although things seemed to be solid between Kardashian and Austin, the two mutually parted ways shortly after due to their long distance.

“There’s no huge reason except their distance apart,” a source close to the couple told the publication, “With his season and Kim’s filming [“Keeping Up with the Kardashians”] it just slowly split them apart.”

The source added, “They tried to keep it as low profile as possible when they were together. They were acting as if they were single or just having fun, but they never were – it was the real deal. They were always strong, but before Kim left for Europe they decided it’s not fair that they don’t get to spend more time together and ended it.”

Kim Kardashian once dated this actress' ex

It is without a doubt that Kim Kardashian’s love life is star-studded. Kardashian once dated Gabriel Aubry in 2010. Aubry, a French-Canadian model for Calvin Klein, is also actress Halle Berry’s ex and father of their daughter, Nahla. Aubrey and Kardashian began sparking dating rumors after being spotted sitting together at an L.A. Lakers game in Los Angeles. They reportedly arrived together and were joined by Kardashian’s mother, Kris Jenner.

“They started seeing each other in the last few weeks,” A source told Page Six at the time. “They have been out a few times, he’s visited her house in LA. Sunday’s game was the first time they were comfortable enough to be seen in public together. It’s early days but they’re getting on well.”

After the Lakers game, Aubry and Kardashian continued spending time with one another during the Thanksgiving holiday. Unfortunately, the relationship was short-lived because Berry was reportedly displeased. However, sources say the relationship did not end due to Berry. “It was just too much to handle for Kim,” the source told E! News at the time. “She realized very quickly they were better off as friends.”

Kim Kardashian and Kris Humphries marriage was very short-lived

Kim Kardashian’s marriage to NBA player Kris Humphries came and went, but it was so buzzworthy that we can’t forget it. The reality star sat courtside at the Nets-Trailblazers game in New Jersey to watch the baller play after her split from Gabriel Aubry. A source at the time said the two were getting to know each other. “They’ve been taking it slow but they have so much fun together,” a source told New York Post.

The athlete proposed to the reality star after six months of dating, and the two wed in August 2011. After 72 days of marriage, Kardashian filed for divorce. Kardashian cited the irreconcilable differences as the reason. Kardashian told Andy Cohen that she knew their marriage was doomed during their honeymoon. “That last marriage … that whole situation was just really hard for me,” she explained. “At the time … I just thought, ‘Holy s**t, I’m 30 years old, I better get this together. I better get married.'”

In retrospect, Humphries wished he knew better in the situation. Humphries explained in March 2019, “I was definitely naive about how much my life was going to change. But the one thing that really bothers me is whenever people say that my marriage was fake.”

He continued, “There’s definitely a lot about that world that is not entirely real. But our actual relationship was 100 percent real. When it was clear that it wasn’t working … what can I say? It sucked.”

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