Photo: Dimitrios Kambouris/Getty

Khloé Kardashian’s dating life has had its fair share of ups and downs.
Her whirlwind romance with former NBA playerLamar Odommade headlines in 2009 when the couple got engaged only a few weeks after meeting, and again when Odom’s substance abuse led to the downfall of their marriage four years later.
In 2016, the middle Kardashian sister began dating NBA playerTristan Thompson, with whom she’s had a tumultuous on-again, off-again relationship. Amid numerous cheating scandals and public scrutiny, the pair have welcomed two children together, daughter True in 2018 and a son in 2022.
The Good American founder has received a fair share of scrutiny over her romantic history, which might be why she’s choosing to take a break and focus on herself. In June 2022 whenrumors sparked onlinethat she was dating “another NBA player,” the star quickly shot them down. “Definitely NOT True!!!” she wrote in response to a Kardashian fan page, adding, “I am not seeing a soul. I am happy focusing on my daughter and myself for awhile.”
In February 2023, Kardashian gave fans a similar update when she responded to a Twitter question about her relationship status.
In a July 2023 episode ofThe Kardashians, the mom of tworeflected on some of her past relationships. “Every single day, I feel bad aboutLamar [Odom],” she said, referring to his reputation as a drug user. She added, “Every single day, I feel bad aboutTristan [Thompson]not being on a team right now.”
From her earliest romances to her long-term relationships, keep reading for Khloé Kardashian’s dating history.
Rashad McCants
Bruce Gifford/FilmMagic

Kardashian and the former NBA player began dating at the end of 2008 andannounced their split in January 2009.
“He’s in a different city every day for games,” Kardashian, who was 24 at the time, shared on her blog. “Our time together was just so limited because of both of our schedules that we decided it is best not to be in a committed relationship. The last seven months have been great and we will definitely remain close friends.”
The star also said that the breakup was mutual, but later claimed McCants had cheated on her in an episode of herE!seriesKourtney and Khloe Take Miami. After it aired, McCants toldPage Sixthat the scene, which depicts Kardashian and her older sister Kourtney discovering suggestive messages in his voicemail, was completely fabricated for the show. Not only did Kardashian not have his current phone number, he claimed, but the pair had already broken up before the scene was filmed.
Derrick Ward
John Sciulli/WireImage

In 2009, Kardashian went on a few dates with NFL running back Derrick Ward. He even accompanied the star to Mexico to celebrate her sisterKourtney Kardashian’s 30th birthday, but that was the extent of their relationship, according toPage Six.
Lamar Odom
Kevin Mazur/WireImage

After meeting at a party for fellow NBA player Ron Artest in August 2009, Kardashian and Odom quickly began a relationship andwere engaged only a few weeks later. Nine days after their engagement,the pair were marriedin a lavish Beverly Hills ceremony.
Things seemed to be going well for the couple, who costarred in two seasons of Khloe & Lamar, anE!reality show all about their life as newlyweds. In 2013, however,Kardashian filed for divorce from Odomfollowing months of speculation about the athlete’s substance abuse. The divorce papers were signed in July 2015, but when Odom was found unconscious at a brothel with drugs in his system just a few months later, Kardashian put the proceedings on hold to help him recover.
Theirdivorce was eventually finalizedin December 2016.
Matt Kemp
Frazer Harrison/Getty ; Robert Benson/Getty

The same month that Kardashian filed for divorce from Lamar Odom, she began spending time with Matt Kemp, then a Los Angeles Dodgers outfielder who previously dated Rihanna. Romance rumors swirled after Kemp shared an Instagram post ofKris Jenner’s Christmas tree, but neither of them ever confirmed a relationship.
“They are just friends and have been for a long time,” a source told PEOPLE at the time. “Khloé is absolutely heartbroken right now [over Lamar] and dating someone is the last thing she’s thinking about.”
French Montana
Ethan Miller/Getty

Kardashian and rapperFrench Montana, whose real name is Karim Kharbouch, were first spotted together April 2014 and enjoyed a shortlived romance.
The couple spent plenty of time together that summer, including at Kardashian’s 30th birthday celebration in Las Vegas.They broke up briefly in September 2014and then tried to rekindle their relationship, but according toE! News, ultimately ended things for good in December 2014.
In 2019, the rapper opened up aboutmaintaining his friendship with the reality starin an interview withHaute Living.
“I feel like we had a real dope relationship ― there was no bad blood, nobody did something to somebody that we couldn’t come back from,” he said. “When the love was like that, it’s always going to be like that. Friendship after a relationship is something that’s real hard to do, and I’m glad we’ve been able to do it.”
Rick Fox
D Dipasupil/FilmMagic ; Michael Kovac/Getty

In May 2015, Kardashian went on alate-night dinner datewith former Lakers player Rick Fox.E! Newsreported that the pair were seen arriving separately around 11:45 p.m. and stayed until 1:30 a.m. Their relationship didn’t blossom any further, but the outing certainly sparked romance rumors.
James Harden
Dia Dipasupil/Getty ; Doug Pensinger/Getty

Kardashian and NBA star James Harden began dating in July 2015. That January, the reality starcredited her multi-tasking skillswith helping the couple find time for each other amid their busy schedules.
“I mean, we make it work,” Kardashian toldEntertainment Tonight. “We do make it work. … I do like to put my relationships as a priority and I really try to make that work. As long as people are making the effort to do so, I think anything can work.”
Despite their efforts, the pair parted ways in February 2016. According to a source, Kardashian and Harden’s relationship became strained after her estranged husband Lamar Odom was hospitalized for a drug overdose in October. Kardashian rushed to Odom’s side and paused her divorce proceedings to support his recovery.
“It hasn’t been easy. James obviously has wanted to see her more and be with her more, but she’s felt like she needed to stay in L.A. to be with her family and to deal with Lamar stuff,” the source told PEOPLE at the time of their breakup. “That has put some strain on things.”
Kardashian had previously told PEOPLE that Harden had been understanding while she dealt with Odom’s health issues, saying he had been “very supportive and awesome.”
“I’m just allowing everything to unfold,” she said. “If it’s ever too overwhelming [for him], then I understand that as well.”
Trey Songz
Michael Bezjian/WireImage ; Kris Connor/Getty

In July 2016, Kardashian and Trey Songz were seen kissing at a nightclub in Las Vegas where the musician was performing,ETreported. According toPage Six, the pair attendedKevin Hart’s wedding to Eniko Parrish together the following month.
“They are talking and hanging out, but it’s casual for now,” a source told PEOPLE at the time. Their romance quickly fizzled, but the pair seemed to remain friends as they were spotted chatting atJustin Bieber’s birthday party in 2022.
Tristan Thompson
Jerritt Clark/Getty

Kardashian and Thompson began dating in September 2016 when the NBA player was expecting his first child with ex-girlfriend Jordan Craig, though both Kardashian and Thompson have maintained that he was single when they first connected.
After months of public outings and plenty of PDA, the pair spent the holidays together andmade their relationship Instagram officialin January 2017. In September 2017, PEOPLE confirmed that they wereexpecting their first child together.
Despite the scandal, Kardashian was willing to give Thompson another chance for the sake of their daughter. “She is committed tokeeping her family together,” a source told PEOPLE. “And Tristan has shown that he is committed to Khloé, so Khloé will make it work.”
However, less than a year later in February 2019,Thompson was accused of cheatingon the star with Kardashian family friendJordyn Woods. After Woods admitted in an interview that Thompson kissed her but denied any intent to pursue him, Kardashianlashed out on Twitterand accused her of breaking up her family. Kardashian quickly walked back her statement, saying: “I’m a rollercoaster of emotions & have said things I shouldn’t have. “Honestly, Tristan cheating on me & humiliating me, wasn’t such a shock as the first time … but Jordyn is not to be blamed for the breakup of my family. This was Tristan’s fault.”
The pair then put a pause on their romantic relationship to focus on being co-parents, reuniting for the first time in public atTrue’s first birthday party.
Thecouple split againin June 2021 after Thompson was seen partying with multiple women in Los Angeles, but continued to amicably co-parent their daughter.
Conflict arose yet again when in December 2021 it was revealed that Texas personal trainer Maralee Nichols wasexpecting a childwith Thompson. Thompsonpublicly admitted to cheatingon Kardashian with Nichols and fathering the child, while offering an apology to Kardashian.
Kardashian took alie detector testin December 2022. During the interrogation, her sisterKourtney Kardashian Barkerasked her to reveal whether or not she was still sleeping with Thompson.
“No, I am not. I’m really not,” the reality star said. The polygraph examiner confirmed that Kardashian was telling the truth, to which she replied: “I would die if it said I was.”
source: people.com