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He had an on-again, off-again relationship with Kourtney Kardashian that lasted for nine years, but his excessive partying ultimately led to their demise.
Nowadays, the reality star is helping Kourt raise their three kids.
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Damon Thomas
He was Kim's first husband back in 2000 when she married him at the age of 19. The couple split four years later. Today, he's not living the high life like his ex-wife. Damon reportedly filed for bankruptcy, claiming to have more than $3 million worth of debt.
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Nick Cannon
The America's Got Talent host has been open about his 2006 relationship with Kim, but these days, he isn't so lucky in love. He separated from wife Mariah Carey in 2014.
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Adrienne Bailon
The former Disney star dated Rob Kardashian from 2007 to 2009, but broke up with him after he admitted to cheating. These days, she's in a much better place and engaged to Israel Houghton. She has said that dating a Kardashian "hurt her career."
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Miles Austin
He briefly dated Kim in 2010, but the couple split because they were long distance. Today, he's married to longtime girlfriend Stacy Sydlo and is a free agent in the NFL.
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Derrick Ward
The former NFL player dated Khloé for four months before they broke things off in August 2009.
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Rashad McCants
The basketball player appeared as Khloé's boyfriend on an episode of Kourtney and Khloé Take Miami, but they broke up after she caught him cheating in 2009. He's currently a free agent.
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Reggie Bush
We all thought the NFL player and Kim were going to make it as a couple, but their on-again, off-again relationship officially came to an end in 2010. In 2014, he married Lilit Avagyan (who happens to look a lot like Kim!) He currently plays for the Buffalo Bills.
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Kris Humphries
The NBA player's marriage to Kim — which lasted a whopping 72 days in 2011 — was highly documented on television, but these days, Kris keeps a much lower profile. He currently plays for the Atlanta Hawks.
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Rita Ora
The actress supposedly dated Rob in 2010, but they split after she allegedly "cheated with 20 dudes" — as the reality star so charmingly claimed on Twitter at the time. She's since been linked to Calvin Harris and Ricky Hil.
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The Game
The rapper claims to have slept with Kourtney, Kim and Khloé Kardashian in his song, "Sauce."
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Ray J
Ahh, the man that started it all. Ray J made the infamous sex tape with Kim in 2003 that was leaked in 2007. He released a single in 2013 titled, "I Hit it First" — an obvious jab at his former girlfriend. Last month, he married Love & Hip Hop: Hollywood's Princess Love.
