Mystery Private-Equity Investor

On 21 June, E! News [9] reported that Kardashian was dating a private-equity investor introduced to her at a dinner by her sister Kim. However, it seems the reported romance was short-lived. On 6 Aug., a source told E! News [10] the couple "slowly fizzled out over the last few weeks."

It doesn't sound like things were serious between the two. E! News also reported that Kardashian and her mystery man only went on a few dates, and she wasn't interested in "forcing anything."

Tristan Thompson (2016-2021)

Khloe Kardashian and Tristan Thompson's relationship has been anything but smooth sailing. The two initially met in September 2016 and started dating shortly thereafter. At the time, Thompson was expecting a child with Jordan Craig, though it is unconfirmed whether or not the two were still together at the time, per People [11]. The couple enjoyed the remainder of the year with Halloween [12] festivities, holiday gatherings, and basketball games.

By April 2017, Kardashian revealed to The Evening Standard [13] that the two were open to starting a family together, saying, "We've talked about it. He [already] is a father and I know for a fact that he would be an impeccable father. I definitely want to be a mom. But I don't put the pressure on it." In 2017, People [14] revealed that Kardashian was expecting her first child with Thompson in September, though she did not personally confirm the news until months later in December via Instagram [15], writing in part, "My greatest dream realised! We are having a baby! I had been waiting and wondering but God had a plan all along. He knew what He was doing. I simply had to trust in Him and be patient."

Unfortunately, the birth of her daughter True Thompson on 12 April, 2018, was partially overshadowed when news that the basketball player cheated on her broke just a day before. Since the initial reports of Thompson's infidelities, the couple were in an on-again, off-again relationship over the next three years, which was further complicated by more cheating accusations, including one with Jordyn Woods [16], Kylie Jenner [17]'s best friend at the time. In February 2019, Thompson and Woods allegedly locked lips at his home after a night of partying, as reported by Us Weekly [18]. The scandal completely dismantled Kardashian and Thompson's relationship, though Thompson initially denied the kiss ever happened. In March 2019, Woods appeared on "Red Table Talk [19]" to share her side of the story, saying, "[There was] no passion, no nothing. He just kissed me." The couple seemed to take a break for the remainder of 2019, and rekindled their relationship in June 2020, as per People [20]. The two dated on and off throughout 2021, with Kardashian ending their relationship after news broke of Thompson's involvement in yet another cheating scandal. This time, it involved not only cheating on Kardashian, but fathering a child with Instagram model Maralee Nichols. In December 2021, the pair were officially over, with a source telling People [21], "Tristan and Khloé have been broken up for a while, and things are okay between them."

As of April 2022, both Kardashian and Thompson are dedicated to coparenting True and remain friends. The "Keeping Up With the Kardashians" star opened up to Robin Roberts about the state of her relationship with Thompson, telling GMA [22], "I still think he's a great guy, and he's a great dad. He's just not the guy for me."

On 5 Aug., 2022, it was confirmed that Kardashian and Thompson had welcomed their second child [23], a son, via a surrogate. However, they have no current plans to reunite romantically and instead are focusing on coparenting.

James Harden (June 2015-February 2016)

Kardashian started dating NBA player James Harden in June 2015 after meeting the basketball player at Kanye West [24]'s birthday party at the Staples Centre. Throughout their eight months of dating, Kardashian and Harden experienced some heavy stuff together, particularly the October 2015 overdose of her ex-husband Lamar Odom. Harden supported Kardashian through the crisis, according to the "Keeping Up With the Kardashians" star herself. She told E! News [25] in November 2015, "James has been great… he's been really supportive, really understanding."

The two's conflicting schedules ultimately led to their breakup in February 2016, with a source telling E! News [26], "Nothing really [bad] happened" between them. They just barely saw each other the past few months and it died out."

Harden later revealed in a 2017 interview with Sports Illustrated [27] that the intense spotlight on their relationship was a contributing factor to the two breaking up. "I didn't like all the attention. I feel like it was for no reason. I wasn't getting anything out of it except my name out there and my face out there, and I don't need that. It wasn't uncomfortable, but it wasn't me," the NBA star said.

French Montana (April 2014-December 2014)

Moving on from her divorce from Lamar Odom, Kardashian dated rapper French Montana for approximately eight months in 2014. The two initially started dating in April and had a whirlwind summer romance together, with Montana accompanying his new girlfriend to her 30th birthday celebration in June 2014. Kardashian was featured in the music video for Montana's song "Don't Panic [28]" in August 2014, and their relationship was documented in the "Keeping Up With the Kardashians" spinoff series "Kourtney & Khloé Take the Hamptons."

In September 2014, the pair broke up for the first time, but they rekindled their romance sometime around his birthday in November. It did not last long, however, and they broke up for good in December 2014, according to People [29]. At the time of their breakup, Kardashian revealed on "Kourtney & Khloé Take the Hamptons" that she rushed into the relationship because she was lonely and destructive. "It's nothing against French. I just think I don't want a boyfriend," she said (via Us Weekly [30]).

Montana later opened up about his relationship with Kardashian in a 2019 interview with Haute Living [31], saying, "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 continued, "The love was real. 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."

Lamar Odom (2009-2013)

Kardashian met NBA player Lamar Odom at a party in August 2009, according to InStyle [32]. The pair instantly connected, and within a few short weeks, Odom proposed to Kardashian with a 12.5-carat ring, as per Forbes [33]. A source told People [34] at the time, "She and Lamar started talking about getting married really soon after they met. They knew this was it, and they are just having fun with this whirlwind." The pair married just nine days after getting engaged, with a special episode of "Keeping Up With the Kardashians [35]" dedicated to their marriage. A source told Us Weekly [36] at the time, "Khloe and Lamar [wanted] to get married before Lamar has to go away for training, and the [basketball] season starts up [this fall]."

The pair's relationship continued to move quickly, and by November 2009, Kardashian and Odom purchased a $4 million mansion in California, as reported by People [37]. By 2011, the couple had their own "Keeping Up With the Kardashians" spinoff series called "Khloe and Lamar" which focussed on their lives together, along with their friends and family. The show lasted two seasons and ultimately ended in 2013. In a 2011 interview with The LA Times [38], Odom admitted that the attention and being in front of the cameras "wore him down."

2011 was a tough year for Odom. He lost his 24-year-old cousin in a tragic murder, and after leaving his cousin's funeral, Odom was involved in a car accident which resulted in the death of a 15-year-old pedestrian, according to NBC News [39]. A series of tough years would follow for Kardashian and Odom, with Odom often making headlines for alleged infidelities, drug abuse, and excessive partying. Odom later said in his 2019 memoir "Darkness to Light" that he was a sex addict and cheated on Kardashian throughout their marriage. "I wanted to take it back, but you can't. [I] wanted to hide it. But that sick sin was hard for me to hide . . . I had a problem," the NBA star said (via People [40]). Kardashian filed for divorce in December 2013, one month after Odom was arrested for driving while intoxicated, per TMZ [41]. On separating from Odom, a source told Us Weekly [42], "She flip-flopped several times, but she can't imagine having kids with someone who refuses to seek help for his disease." In October 2015, Odom overdosed in a Nevada brothel. At the time, he was hospitalised after suffering multiple strokes and was in a coma for four days, according to People [43]. Kardashian remained by Odom's side throughout his recovery, and their divorce was paused so she could help him while he was hospitalized. The divorce was ultimately finalised in December 2016 [44].

Derrick Ward (2009)

After her short-lived relationship with McCants, Kardashian went on a couple dates with NFL running back Derrick Ward. Ward accompanied Kardashian to Mexico to celebrate sister Kourtney Kardashian's 30th birthday, as reported by Us Weekly [45]. The two did not pursue one another past a few dates, and Kardashian quickly moved on to her eventual husband Lamar Odom.

Rashad McCants (Late 2008-January 2009)

Kardashian's first romance in the spotlight was with then-Minnesota Timberwolves player Rashad McCants. The two briefly started dating sometime in late 2008, with McCants seen as Kardashian's date at a Las Vegas nightclub in December 2008. The two's fling was short-lived, however, and Kardashian accused McCants of cheating on her and "hooking up with girls on Facebook" in an episode of "Kourtney & Kim Take Miami," as reported by The Mirror [46]. In January 2009, the pair officially split. McCants has vehemently denied ever cheating on Kardashian, and even went as far to argue that the reality TV star's allegations were "made up." McCants told Page Six [47] in November 2009 that the two had "had already called it quits" when she allegedly found evidence of him cheating.