When it comes to their quest for love, the Kardashian family has seen some pretty dramatic highs and lows! They’ve experienced nasty divorces and epic feuds with their exes. But despite their constant run-ins with heartbreak, they always end up giving the love game another try. But if you’ve been struggling to keep up with the family’s epic makeups and nasty splits, we’ve gathered all of the Kardashian crew's biggest breakups and relationship fails!
Before finally finding her Mr. Right in her husband, Kanye West, Kim Kardashian had a great deal of failed relationships and marriages!
Kim married producer Damon Thomas back in 2000. But the pair ultimately divorced, with Kim claiming that Thomas abused her physically and emotionally during their time together.
She then went on to walk down the aisle with basketball star Kris Humphries, with their marriage lasting only around 10 weeks before they announced they were separating! The union was eventually annulled.
Along with her marriages, Kim also has had several boyfriends, including her very high-profile relationship with Reggie Bush.
She also dated Nick Cannon and Nick Lachey following his divorce from Jessica Simpson.
And who can forget probably her best known ex-boyfriend and sex tape partner, Ray J!
Along with those fellas, Kim has also previously been linked to Halle Berry’s baby’s father and ex Gabriel Aubrey, John Mayer, Michael Copon and soccer superstar Cristiano Ronaldo.
It seemed like Khloe Kardashian hit the jackpot when she married Lamar Odom. However, their fairytale eventually turned sour as Odom faced both cheating and drug abuse allegations just a few years into their union.
Khloe rebounded from her now estranged hubby with her on-and-off rapper flame French Montana!
And basketball legend Rick Fox has also been named as one of her possible suitors as she reportedly holds out for Odom to get his act together!
But Khloe has most recently been spotted cozying up to James Harden, sticking to her theme of love and basketball!
Along with the guys just listed, Khloe has also been previously linked to basketballer Rashad McCants and footballer Derrick Ward.
Before Rob Kardashian ditched the spotlight, the KUWTK's fan favorite had a few high-profile relationships of his own.
When his family’s Keeping Up With the Kardashians reality show first took off, Rob was spending his time with his sweetie Adrienne Bailon. But the adorable duo ultimately broke up after the actress and singer said she found out Rob had cheated on her.
Rob then moved on to signer Rita Ora, which turned out to be a questionable decision for the reality star. And his toxic relationship with the singer has actually been named as one of the possible reasons for his reported depression and reclusive behavior over the past few years!
Kourtney Kardashian has been one of the most consistent members of the Kardashian crew when it comes to her love interests, with her last ten years being devoted to her charming but troubled boyfriend, Scott Disick.
But not even the couple’s three kids and years of history could keep the pair from breaking up yet again this year when Disick faced yet another round of cheating and substance abuse allegations!
The Kardashian kids’ momager isn’t immune to heartbreak either! Kris Jenner parted ways with Caitlyn Jenner in 2014 after over 20 years with her ex!
Before marrying Caitlyn, Kris was married to Robert Kardashian, who she has admitted to cheating on!
And her ex-lover Todd Waterman has also spoken out about their reported trysts during the time she was dating Caitlyn ahead of the pair's marriage!
Unfortunately, the youngest member of the Kardashian-Jenner crew, Kylie Jenner, recently had her own taste of serious relationship drama when her alleged boyfriend, Tyga, was caught in a cheating scandal.
Tyga was blasted for being involved with and sending a nude photo to a transgender woman named Mia Isabella, with an alleged text message thread showing that he was possibly cheating with the woman during his relationship with Kylie and when he was still dating his ex Blac Chyna! What do you think is the biggest Kardashian relationship fail? Tweet us @OKMagazine or let us know in the comments section below.