Whether we love the Kardashian/Jenner sisters or hate them (our feelings are a little complicated, to be honest), there are some things that are just straight-up facts about them. They are unbelievably famous, they spend more money on their kids' wardrobes than most of us make in a year, they have a casual relationship with the truth when it comes to photo editing and questions about plastic surgery, and they have some of the absolute worst luck when it comes to finding healthy, long-term relationships.
It can be hard to know how much of finding a good, loving partner is luck and how much is choosing the right partner. For the Kardashian/Jenner sisters, we'd say their romantic troubles are probably a combination of both. Although we can argue about which sister has the worst taste in men (the answer, for the record, is Kylie), we can't deny that all of them have had to deal with romantic drama in the public eye. From being accused of being an NBA groupie (Kendall) to getting cheated on multiple times by multiple partners (poor Khloé) to having an ex threaten to beat up a new boyfriend (Kim), these famous sisters have been through it in the name of love.
Read on for our assessment of why the Kardashian sisters are so unlucky in love.
Controlling Ye
Even before Kim and Kanye West's six-year marriage ended in flames, thanks at least in part to Ye's ongoing mental health struggles, there was just something so sad about their relationship. While the two seemed totally in love, fans couldn't help but notice how controlling Ye could be of Kim's appearance, including basically telling her — in a scene captured on Keeping Up With the Kardashians — that all of her clothes were unfashionable and needed to be replaced. That's a red flag moment for sure!
Kendall the Groupie?
Even though Kendall Jenner has dated several high-profile people (including Harry Styles and a Jonas brother), she's most known for her streak of dating NBA players. She tends to keep her relationships the most private of the sisters, but that doesn't mean she hasn't had to deal with drama. For her, that has meant clapping back at people on social media who like to imply that she's basically a glorified NBA groupie. We're not here for any of that slut-shaming kind of nonsense.
The Trouble With Tyga
Kylie's first big public relationship was with rapper Tyga, and it was problematic. The pair started dating when Tyga was in his mid-20s and Kylie wasn't even 18, an age difference that Tyga himself referenced in his song "Stimulated." With lyrics like, "They say she young, I should've waited / She a big girl, dog, when she stimulated," the song is basically his ode to having sex with Kylie before she was a legal adult. Gross.
Khloé & Lamar
Khloé and Lamar Odom famously got married after only a month of dating, and that turned out about as well as one would expect. The pair split up after four years, which included multiple incidents of Lamar cheating on Khloé and at least one incident of Khloé getting into a physical fight with a stripper she found in Lamar's hotel room. Classy all around!
Kourtney & Scott: Part 1
Here's how we know that the Kardashian sisters have terrible taste in men: Even their male friends are problematic. The sisters have long been friends with Joe Francis (who created Girls Gone Wild and has been convicted of everything from child abuse to assault and tax evasion), and it was at this stellar human being's house where Kourtney first met Scott Disick. The two ultimately had three kids together, but it was never a smooth ride for them as they frequently broke up and dealt with allegations of infidelity and substance abuse problems.
Pete, Kim, & Ye
Kim seemed to really fall hard for comedian Pete Davidson, and he was into her enough to add her and her kids to his tattoo collection. But the relationship was short-lived (the pair dated for less than a year) and probably wasn't helped by Ye's public threats against Pete. Kim is still apparently single now, but Pete has moved on to a new girlfriend and has allegedly removed or covered up his Kim tattoos.
Travis the Cheater?
Just like her sister Khloé, Kylie is no stranger to rumors that her man is cheating on her. One woman, Rojean Kar, has taken to social media several times to talk about her life as Travis Scott's "side-chick." Can we be honest and say that we totally don't get why multiple women would be fighting for Travis? At least Tristan Thompson is cute! Travis just looks like he smells like weed 24/7 (which Kylie has confirmed). And he never makes eye contact.
Tristan the Cheater
There's probably never a great time to find out that one's partner has been unfaithful. But we're not sure there is a worse time to find that out than right before having a baby with that person! That has sadly been Khloé's reality and the cause of her first big breakup with Tristan Thompson. Notice we said "first" in that sentence, because Khloé is the queen of second (and third and fourth) chances.
Kylie's Friendship Loss
Another casualty of the Kardashian sisters' unlucky love lives was the years-long friendship between Kylie and former BFF Jordyn Woods. Jordyn got the heave-ho after being caught kissing Tristan Thompson, who, to be fair, seems willing to kiss just about anyone with lips. Kylie sided with Khloé, even when Khloé still went back for more with Tristan.
Kim & Ray J
Kim and rapper Ray J dated for three years and, of course, famously made at least one sex tape together. For years, Kim has claimed that tape was released without her knowledge, but Ray J has since gone on the record with the Daily Mail and spilled all the tea, including that Kris Jenner was behind the whole thing. It's true what they say: The devil works hard but Kris Jenner works harder.
Scott the Gossip
It's probably normal to have some feelings when a person you've been with off and on for a decade moves on in a super public way, but damn, Scott got so messy. In 2022, he sent Younes Bendjima (another of Kourtney's exes) a shady DM about Kourtney's PDA with her now-husband, Travis Barker. Younes put Scott on blast on Instagram, and it was all so very high school.
Not the Right Kris
Kim famously tied the knot with NBA player Kris Humphries in 2011 — but stayed married for a mere three months. It turned out that Kim really only had love for one Kris in her life, and there was no way mom Kris was going to give up that slot!
Tristan the Baby Daddy
Tristan Thompson is now a father of four kids, so we can't help but wonder if he's going for a full starting five basketball team lineup? Tristan famously had a child with another woman after Khloé took him back after the first cheating scandal. At this stage of the game, it seems like it would be fair for poor Khloé to wonder if any men are faithful, ever? Or maybe she just needs to look outside the NBA for her next man.
Drake Drama
We're not here to slut-shame anyone (adults can do what they want with consent), or to say for sure that Drake has been involved with anyone in the Kardashian circle. But we will say that the persistent rumors that Drake has hooked up with not only Kim but also Kris (and maybe Kylie, too) just seem like more evidence that Kardashian love lives are messy.
Did Khloé Fake It?
Khloé's first NBA boyfriend was Rashad McCants, whom she dated for about seven months between 2008 and 2009. She initially blamed the breakup on their busy schedules but then filmed a scene for an episode of Kourtney & Khloe Take Miami that implied that Rashad had cheated on her. Rashad slammed Khloé in the press, telling Page Six that the reality star had "made the whole thing up." This isn't a great look for Khloé: Either she got cheated on (which is terrible) or she lied about getting cheated on (which is a different kind of terrible). But bottom line, not so lucky in love … especially with NBA players.
