Keeping Up With The Kardashians star Kim Kardashian has had quite an interesting dating history prior to marrying Kanye West.

From Halle Berry's ex-husband to Kanye West, Kim Kardashian has been romantically involved with several people in the entertainment business. Now that the SKIMS founder and the Yeezus founder may be over for good, she might consider going back to a former flame. Otherwise, it is still good to revisit Kim's dating history to see which mistakes she's made over the years.

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According to Page Six, a 19-year-old Kim Kardashian reportedly eloped with music producer Damon Thomas back in 2000. In court documents from their divorce filings, Kim claimed she was high on ecstasy for the ceremony and their relationship did not end amicably. The divorce was finalized in 2004. Kim then met Ray J in 2005 while she was working as Brandy's assistant. Ray J wrote in his book, Death of a Cheating Man: What Every Woman Must Know About Men Who Stray, that Kim pursued him while she was still married. She broke things off with her then-husband to be with Ray J, so he claims that he felt obligated to be with her. In 2007, a sex tape between them was leaked. Kim later tried to sue to prevent the tape from being released, but that didn't go anywhere.

One of Kim Kardashians's more famous relationships is when she dated football player Reggie Bush. The couple dated on and off between 2007 and 2010, and they were apparently still in touch until she got married to Kris Humphries in August 2011. Reggie was reportedly leaving her text messages and voicemails saying that she was making a huge mistake and that he was the one for her. Nonetheless, even Kayne's ex-girlfriend, Amber Rose, claimed in 2012 that Kim cheated on Reggie with Kanye while he was still with Amber. In April 2010, it was reported that Kim and soccer player Cristiano Ronaldo had hooked up while she was on vacation in Madrid, which was shortly after the two met at the Beverly Hills Hotel. But that fling did not last long as Cristiano was spotted with model Irina Shayk.

In 2010, Kim began dating basketball player Kris Humphries. After just six months of dating, Kris proposed to Kim, and she said yes. In August 2011, the couple was married in a lavish ceremony that took place in California. But as documented on Keeping Up With The Kardashians, she filed for divorce just 72 days later.

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Sources: Page Six