KUWTK: A Look At Khloe's Dating History Throughout The Years

Out of all the Kardashian-Jenner sisters, Khloé Kardashian's love life is often the topic of discussion. Compared to her siblings, the third eldest Kardashian hasn't had the best luck with her relationships. On the other hand, Khloé has a thing for athletes and musicians like her sisters. Khloé's path to love isn't the easiest and often proves to be the most complicated. Between infidelities and incompatibilities, it's safe to assume that Khloé isn't Cupid's favorite. However, she remains steadfast in her journey to finding Mr. Right.

As of May 2021, Khloé is rekindling with her beau, NBA star Tristan Thompson. Their relationship is quite tumultuous, and often buzzworthy due to Thompson's repeated infidelity. Most recently, the Boston Celtics forward has made headlines for allegedly cheating on Khloé (again) with Instagram model Sydney Chase. The drama continues with the alleged love triangle. In the meantime, let's take a look at the lovers of Khloé Kardashian's past.

Rashad McCants blames Khloé Kardashian for his NBA career failing

Khloé Kardashian may date rappers and actors from time to time, but it's rather obvious that the reality star has a special place in her heart for athletes. In 2009, Khloé dated former NBA player Rashad McCants from 2008 through 2009 before calling it quits. During a November 2009 episode of "Kourtney and Khloé Take Miami," Khloé claimed that McCants cheated on her with multiple women.

At the time, a source told Perez Hilton (via Mirror): "[Khloé] confronted him, and he reacted angrily and tried to deny the story at first before admitting that it was true."He'd been hooking up with girls over Facebook for the past two weeks." McCants later denied those allegations, telling Page Six that the whole scene was fake because they were already split by then. According to McCants, the two lovers parted ways in January 2009.

It is unclear where these two lovers stand today. However, McCants says he regrets his highly publicized relationship with the E! personality. According to the former Sacramento Kings shooting guard, his career in the NBA was cut short due to his relationship with Khloé. As written by the Observer (via Sports Illustrated), people doubted his "commitment to the NBA," which resulted in McCants not being re-signed by the team after one season.

He told the publication, "Without that situation in play, I'm a $60–70 million player. Easily." Yikes much?

Khloé Kardashian and Derrick Ward's relationship ended amicably

Before meeting Lamar Odom, Khloé Kardashian was romantically linked to Derrick Ward, who played for the Tampa Bay Buccaneers at the time. The two dated briefly after her split from Rashad McCants. According to Ward, he met Khloé through Reggie Bush, who was dating her sister Kim Kardashian at the time. Per Us Weekly, the pair was spotted showing some real PDA at Kourtney Kardashian's 30th birthday in Mexico. Their relationship ultimately ended amicably, with the two former lovers eventually finding significant others after one another.

Despite the mutual end of their relationship, Ward is not exempt from bad publicity like the rest of Khloé's previous lovers. In January 2018, Ward's then-wife Naomi Lee Allen-Ward filed a restraining order against him. She claimed the athlete was verbally, emotionally and physically abusive toward her, per TMZ. She also revealed that the former NFL star tried to kill her. Clearly, Khloé dodged a bullet by leaving McCants.

Khloé Kardashian and Lamar Odom's marriage saw great hardships

Khloé Kardashian's most notable relationship is her tumultuous marriage to former Los Angeles Lakers star Lamar Odom. The reality star married Odom in September 2009, just a month after they first met. The marriage seemed like a happy ending for Khloé at first, but things slowly took a turn for the worse. Their romance ended in 2013 after Odom admitted to his drug use and infidelity with two prostitutes. Two years later, Khloé called off her divorce after Odom overdosed at a brothel in Las Vegas and nearly died. Khloé stayed by his side through it all, and the two eventually rekindled their relationship. Unfortunately, Khloé filed for divorce once more. Their divorce was finalized in 2016.

In retrospect, Odom wrote about his love and hate for his wife of six years in his autobiography, "Darkness To Light." Recalling a time where he drove to see Khloé, he wrote (via Showbiz Cheat Sheet), "We did ninety miles an hour all the way, yet it felt like the drive took forever."

He continued, "But it still wasn't enough time to find the right words to say to Khloé. I searched all night for the perfect words, and they never came. I hated her and loved her all at once. I could kiss her and curse her in the same breath. But I was desperate to talk to her. I knew this was my last chance." Since their divorce, Khloé and Odom have remained cordial with one another on social media.

Khloé Kardashian and French Montana remained friends after their split

Khloé Kardashian's relationship with rapper French Montana marked her first serious romance since her divorce from Lamar Odom. The two began secretly dating in 2014, but their relationship was confirmed in April of that year. From that point on, Khloé and French made their romance public. In June 2014, the "Unforgettable" rapper was at Khloé's side for her 30th birthday celebration in Las Vegas. Additionally, Khloé and the rapper spent a lot of time together in the Hamptons while filming "Kourtney and Khloé Take The Hamptons."

Although it seemed like everything was peachy for these two lovebirds, their relationship ended swiftly. Khloé and French parted ways after eight months of dating, per E! News. An insider close to Khloé revealed that she ended things with French because of his "needy, obsessive" behavior and she slowly began distancing herself. The lovers tried to rekindle their relationship, but no luck. Despite the way they ended, the two continue to keep in contact. In fact, the rapper was part of Khloé's support system following her messy split from Tristan Thompson in 2019.

"Khloé has been leaning on her ex French in the last several months," a source told Hollywood Life (via Cosmopolitan). "French is someone that Khloe has always been able to trust and talk to about things. They still have great chemistry together." How sweet!

Khloé Kardashian and Rick Fox once sparked dating rumors

Following her split from French Montana, Khloé Kardashian went back to dating athletes again. This time around, she had sparked dating rumors with retired NBA star Rick Fox. In May 2015, the two were spotted at a Los Angeles restaurant with one another, and witnesses say it seemed like the two were on a date. "It looked to be a fun date," one witness told Us Weekly at the time. "She seemed happy." An insider also revealed to the publication that Khloé reportedly had a crush on Fox after knowing one another for a few years prior.

The following morning, Khloé posted a selfie on Instagram wearing sunglasses and holding her head. She revealed she had a hangover in the caption, writing, "Ugh my head.....Hangovers are the worst... this flight to Dubai will be utilized well with this long a** nap I'm about to take... I look rough lol." Clearly, the two had too much to drink that night.

It was later clarified that the two were talking about business and Lamar Odom. "This was not a date and they were talking business and Lamar," a source told Hollywood Life. "The NBA is small fraternity, and both Rick and Lamar are former Lakers and former rivals. They know each other very well."

Khloé Kardashian and James Harden's relationship ended because of Lamar Odom

When Khloé Kardashian and James Harden met at Kanye West's birthday party in June 2015, sparks instantly flew between the two. After their introduction, the two began hanging out with one another frequently, especially during Fourth of July weekend that year. According to The Indian Express, the couple was spotted on a dinner date in Las Vegas and were reportedly "snuggling side by side during the meal."

Less than a year later, the two ended up splitting over Lamar Odom. When Odom overdosed at a Nevada brothel, his still-wife stayed by his side. Throughout the ordeal — which took a number of weeks — Khloé remained attentive to Odom, ultimately causing the end of her relationship with Harden. Additionally, Khloé and Harden had some major trust issues at the time. 

After their split, revealed that she broke up with the NBA player because he wasn't monogamous. "I just don't want to put up with people that you want to be monogamous but then they're not monogamous," Khloé explained to Lisa Rinna during an episode of Kocktails with Khloé (via Entertainment Tonight). "I've always said, 'It's long distance. I've always said, 'We don't need to be monogamous! There's a lot of s**t going on in our lives. You live in Houston. I live in L.A. Let's see each other when we see each other.'"

On the other hand, James Harden described the relationship as the "worst year" of his life in a 2017 Sports Illustrated interview. Harden obviously isn't keeping up with Khloé anymore.

Khloé Kardashian and Trey Songz dated briefly

After splitting from James Harden, Khloé Kardashian created even more buzz surrounding her love life when she sparked dating rumors with R&B singer Trey Songz in 2016. The two were first spotted together at Khloé's 32nd birthday party. Additionally, Khloé and Trey were spotted on a Topgolf date in Las Vegas, according to E! News. The two were also caught making out after one of Trey's concerts. Despite the PDA, a lot of critics came for the reality star for dating the singer, especially because the latter is actor Lauren London's ex — you may remember London as a bridesmaid at Khloé's wedding to Lamar Odom. 

The two never confirmed their relationship themselves, but a source revealed the two were dating. "They are dating," the insider told Us Weekly. "The relationship is very new, but she's having fun." The alleged fling lasted a few months before it fizzled out.

The cheating rumors continue to haunt Khloé Kardashian and Tristan Thompson's relationship

Khloé Kardashian's second-most notable relationship is her complicated romance with Tristan Thompson. She met the Cleveland Cavaliers player through her best friend, Malika Haqq, in August 2016. Their relationship quickly escalated, as the two were spotted everywhere from Mexico to Miami. In September 2017, Khloé and Thompson revealed they were expecting their first child. In April 2018, the two welcomed their first child, True Thompson.

Just days before True's birth, Thompson made headlines for cheating on Khloé with multiple women. Despite Thompson's initial infidelity, the two endured through their issues. However, the on-and-off couple broke up in February 2019 after he was caught being unfaithful again — this time with Kylie Jenner's best friend, Jordyn Woods

Almost a year and a half after splitting, Khloé and Thompson began rekindling their relationship. A source revealed to People in July 2020 that the NBA star was working on proving himself worthy of a second chance with Khloé, which clearly worked out in his favor. While the two are reportedly considering Baby No. 2, new cheating rumors have surfaced in April 2021 after Instagram model Sydney Chase came forward on a podcast about allegedly hooking up with Thompson. The drama between them continues to get messy, but of course, we can't keep our eyes off of Khloé and Thompson's relationship.