1. Scott Disick: The Baby Daddy

While tumultuous romances are a dime a dozen in Hollywood, Kardashian and Disick’s relationship takes it to another level.

They first broke up in 2015 and started seeing different people. But a year later, Disick posted a photo of them kissing, which seemed to imply they were back together. The two eventually split up again in 2017 for good.

Despite it being five years since their last break-up, Disick has never quite seemed to get over their relationship. On the last episode of KUWTK in 2021, he shared that he was still hoping for a reunion with Kardashian; and in 2022 on Hulu’s The Kardashians, she called out Disick for snarky comments he made about her new relationship.

2. Justin Bieber: The Rebound

After her first break up with Disick in 2015, Kardashian rebounded with pop superstar Justin Bieber. The two were spotted leaving Hollywood club The Nice Guy together, before heading The Montage hotel in Beverly Hills.

Sources told Gossip Cop that the two were “casually hooking up”, and Bieber even posted a photo of himself with a mystery woman on Instagram; many fans speculated that it was Kardashian.

When asked on The Bert Show about his relationship with Kardashian, Bieber joked that he was just a rebound: “I’m being used, man. What can I say?”

Eventually, the two stopped being seen together, and Kardashian was reported to have reunited with Disick once again.

3. Younes Bendjima: The Boy Toy

After finally calling it off with Disick, Kardashian got together with Algerian model Younes Bendjima at Paris Fashion Week in 2016. He’s 14 years her junior and would be her next long-time partner.

Despite starting their relationship on such a serious note, it was clear that the two just wanted to have fun: they were frequently photographed cuddling in Cannes and relaxing in St Tropez, and spent the night together in a US$650 airstream trailer in Malibu.

While their relationship lasted a respectable two years, it was clear that they were not meant to be. They broke up in 2019, and Khloé Kardashian tweeted after the relationship ended that Bendjima “was sooooooo toxic and negative for Kourt”.

4. Luka Sabbat: The Fun Fling

Only weeks after her break-up with Bendjima, Kardashian was spotted out and about with Yeezy model Luka Sabbat. This time, the age gap was even bigger: the pair are 19 years apart in age.

Rumours of a relationship started when Sabbat was spotted having dinner with Kardashian at The Nice Guy. Soon, he accompanied her everywhere – to the opening of Tao Chicago, to her son’s Fortnite-themed birthday party, and even on a Kardashian-Jenner trip to Aspen.

But their fling eventually fizzled out. Sabbat confirmed that they were over by telling The Cut in 2019 that, “we’re definitely not dating.”

5. Travis Barker: The One

After several roller coaster relationships, Kardashian finally found her lifetime partner in Blink-182 drummer Travis Barker. They had been friends for several years before they finally decided to give dating a try in early 2021. They confirmed their relationship in February by posting a photo of themselves holding hands in a car.

This was followed by extremely lavish shows of love: Barker sent Kardashian outrageous flower arrangements for her 42nd birthday and on Mother’s Day, while Kardashian posted several photos of their PDA on trips to Utah, on holiday in Italy, and even in Barker’s recording studio.

Barker took things to the next level by proposing on the beach in Santa Barbara in October 2021. Amid roses and candles, he got down on one knee and proposed with a Lorraine Schwartz ring.