Kim Kardashian and Kanye West don't exactly have the best track record when it comes to relationships, so it might actually be more surprising that their marriage has lasted more than half a decade than it is to learn that Kim filed for divorce. Kim's been married three times at 40 years old, and before Kim, Kanye was known to have dated a string of look-alike models and singers and of course, one famous former stripper. But when Kim and 'Ye got together in 2011, it seemed they'd finally accepted that they were meant to be after years of mutual interest.
But now, it's over and we can't help but to take a moment to reflect on all the flighty relationships the two of them had before tying the knot. While Kanye has certainly been a party in some questionable relationships, it's really Kim who gets some major side eye from us — and we're not even Kim haters. Some people may have forgotten that before Kim married the controversial rapper, her ongoing series of seemingly vapid relationships with men of mediocre fame nearly lost her a shot at legitimate fame and threatened to plant her squarely in Real Housewives territory. No matter what anyone says about Kanye, he helped elevate her celebrity, and a look at her past relationships proves it. Don't worry though, keep reading and we'll clue you in on Kanye's dating history, too.
Kanye & Sumeke Rainey
Kanye stuck with his high school sweetheart Sumeke Rainey for years before Kim was even a twinkle in his eye. His relationship with Sumeke even surfaced in his debut album The College Dropout on the track "Never Let Me Down." "Nothing sad as that day my girl's father passed away/So I promised to Mr. Rainey I'm gonna marry your daughter," he rapped, although we now know that never happened.
Kim & Damon Thomas
Long before Kim and her assets became so well known, she married music producer Damon Thomas when she was 19 years old. He's nearly 11 years her senior, so he was already pushing 30 while she was barely out of high school. They eloped in Las Vegas and were together for four years before getting divorced in 2004. Kim has said on Keeping Up With the Kardashians that he was controlling and abusive.
Kanye & Alexis Phifer
Meanwhile, Kanye who's always had an interest in the fashion industry, started dating runway models. In 2002 he started dating Alexis Phifer, but they broke up two years later, shortly after his music career took off. It doesn't end there though, they got back together and got engaged a year later, eventually calling it off after the death of Kanye's mom.
Kim & Ray J
For better or worse, Kim's relationship with singer Ray J made her a household name. Without that sex tape, we're not sure Paris Hilton's former assistant ever would've managed to drum up enough interest in herself to achieve the stardom that likely led to the creation of Keeping Up With the Kardashians.
Kanye & Brooke Crittendon
OK, so get this: While Kanye and Alexis were broken up, he hooked up with Brooke Crittendon, who at the time was an aspiring actress working as an executive assistant for MTV News. She looked conspicuously similar to Alexis, whom he eventually went back to. Brooke went on to badmouth Kanye in the media for years after they split in 2006.
Kim & Nick Cannon
After the whole Ray J debacle, Kim went on to date entertainer Nick Cannon for several months before he married songstress Mariah Carey in 2008. Nick told radio show host Howard Stern that he couldn't get past her lying about the aforementioned sex tape though. "We talked about this tape … And she told me there was no tape," he said. "If she might have been honest with me I might have tried to hold her down and be like 'That was before me' because she is a great girl. She's actually one of the nicest people you'll ever meet. But the fact that she lied and told me that there was no tape? And I still think she might have even had a part to play with its release."
Kanye & Amber Rose
Kanye's most public relationship before marrying Kim was with model, actress, and former stripper Amber Rose, whom he dated for two years. Their relationship seemed filled with drama, and ended with him publicly slut-shaming and insulting her. "I'm a compassionate person, I have empathy," Amber said on the No Jumper podcast in 2020. "I'm a good person. That's why people love me. That's why anybody I've ever dated always loved me. You can't really mention anybody who ever says anything bad about me except for him because I got away. I'm not like him at all. I didn't get anything from him."
Kim & Reggie Bush
Around the same time, Kim started her on-again-off-again relationship with then-NFL running back Reggie Bush. By this point, Keeping Up With the Kardashians was taking off and Kim was regular internet fodder. Though neither has ever confirmed the reason for their breakup, some have speculated that Reggie couldn't handle Kim's growing fame.
Kanye & Selita Ebanks
By this point, Kanye had achieved mega-star status and after a string of unsuccessful long-term relationships, he started dating quite a bit. Shortly after splitting with Amber Rose, he dated model and actress Selita Ebanks some time in 2010. He had also been spotted out with her a couple of years previous and she starred in his "Runaway" music video, though the two never spoke publicly about their relationship.
Kim & Miles Austin
Now firmly in the middle of an athlete kick, Kim started dating former Dallas Cowboys player Miles Austin in 2010. They were coupled up for a few months, but their relationship didn't last long. The two apparently didn't do well with the long-distance nature of their relationship.
Kanye & Melody Thornton
Still dabbling in the dating scene, Kanye briefly dated former Pussycat Dolls performer Melody Thornton in 2010 as well. Apparently Melody and Kim were good friends before Melody and Kanye dated, but stopped hanging out around the same time. Kanye's relationship with Melody only lasted a short while.
Kim & Gabriel Aubry
At this point, Kim seemed to be going through a really awkward phase in her love life as well. After splitting with Miles Austin, she completely broke from her type and dated model Gabriel Aubry (Halle Berry's ex) for a brief while. We did get a peek into that short-lived romance on KUWTK though.
Kanye & Chanel Iman
It's clear that between 2010 and 2011, Kanye's dating habits got pretty casual. He partied a lot and hung out with a lot of women during that time, which is also when he became a regular on the fashion scene. Although she denies that they were together, he was spotted out with model Chanel Iman on more than one occasion. It doesn't appear they had an actual relationship, but it seemed there was something going on between the two of them.
Kim & Kris Humphries
And then of course, there wat that ill-fated marriage between Kim and basketball player Kris Humphries. No one — including her family members — seemed to understand why Kim married Kris in the first place, but their marriage lasted quite famously for all of 72 days before Kim filed for divorce in 2011.
Kim & Kanye
Kim and Kanye started dating practically before the ink was dry on her divorce filing and waited to get married until the divorce from Kris was complete nearly three years later. Kim's concerns about the divorce not being completed before her wedding to Kanye were documented on KUWTK. The couple was married for almost seven years and they have four children together.
