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Kim Kardashian’s Ex-Boyfriends: A Gallery

Before Kris

As Kim Kardashian prepares to wed, a look back at the men she said “I don’t” to.

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As Kim Kardashian prepares to marry Kris Humphries this weekend, a look back at the men she said “I don’t” to, including Reggie Bush, Nick Lachey—and Justin Bieber?

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Running back Reggie Bush can shake linebackers, but he just can’t seem to let go of Kim Kardashian. After the Heisman Trophy winner (and forfeiter) split from the reality-TV princess for the last time in 2010, he began dating Melissa Molinaro, an Old Navy model who looks eerily like Kardashian. But according to Life & Style, Bush is still pining for Kim, who is marrying New Jersey Nets star Kris Humphries on Aug. 20. "He's been sending text messages to Kim and leaving her voice mails, telling her she's making a mistake and that he's the one for her," a source told the magazine. Alas, there will be no Bush and Tush sequel. 

Fame
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What’s the best way to get over a high-profile celebrity? Date a woman who isn’t one. Yet. After his split with Jessica Simpson in 2006, Nick Lachey began seeing Kim Kardashian, then just a Hollywood stylist. The two were set up by former USC quarterback Matt Leinart (who would later introduce Kardashian to his former teammate Reggie Bush). “They're sweet on each other," a source told People."It's the beginning stages of a relationship." But not a very long one. The couple ended things when Lachey started dating Vanessa Minillo, who became the second Mrs. Lachey in July 2011.

Peter Kramer / AP Photo
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It was Kim Kardashian’s relationship with Ray J—younger brother of R&B singer Brandy—that truly propelled her career. But not for the right reasons. The two began dating in 2006, but in February 2007 a sex tape featuring the couple was “leaked” and bought by Vivid Entertainment for $1 million. Kardashian sued for invasion of privacy and received a $5 million settlement from Vivid. By the end of the year, the couple had split, but by then E! had begun airing Keeping Up With the Kardashians. And two years after that, Ray J got his own reality series, For the Love of Ray J.

John Shearer / WireImage
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After her breakup with Reggie Bush, Kim Kardashian merely changed NFL divisions. In July 2010, she went public with Dallas Cowboys Pro Bowl wide receiver Miles Austin, but their relationship was a quick out. By September, the Cowboy had ridden off into the sunset. The couple announced that they ended things, citing distance as the main reason. "With his season and Kim's filming [Keeping Up With the Kardashians] it just slowly split them apart," a source told People.

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One woman’s trash may be another woman’s treasure, but in the case of model Gabriel Aubry and Kim Kardashian, the relationship didn’t last long. In November 2010, the Canadian who had recently split from Halle Berry (with whom he had fathered a daughter), began dating Kardashian, who was on the rebound from Miles Austin. A month later, Kim had moved on, amid reports that she had already been dating her future husband, Kris Humphries.

Noel Vasquez / Getty Images
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Instead of becoming Mr. Mariah Carey, Nick Cannon could have been Mr. Kim Kardashian. If she hadn’t kept cheating on him, that is. The two had an on-and-off relationship for years, but broke up after Cannon found out she had been seeing another Nick (Lachey). The pair reconciled, but only briefly. He broke up with her again after her relationship (and sex tape) with Ray J became public.

Dan Steinberg / AP Photo
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In a hook-up worthy of Kevin Costner and Whitney Houston’s on-screen romance, Kim Kardashian had a one-night stand with her Australian bodyguard Shengo Deane. And in true Kardashian fashion, the whole thing was caught on camera for her reality-TV show. When news of Kim’s engagement broke a few months later, Deane told an Aussie paper:""I'm really happy for her. Kim is such a sweet, nice person—she deserves to be happy." And while he admitted that tabloids had offered him money to talk about their fling, he remained tight-lipped. “That’s just something I wouldn’t do.”

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In April 2010, in between Reggie Bush and Miles Austin, Kim Kardashian found the time (and frequent-flier miles) to go on a few dates with Real Madrid star Cristiano Ronaldo. The two were spotted having dinner and making out in Spain, but it didn’t last long—having fierce spray tans as your only connection just isn’t enough to sustain love.

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Long before she became a household name, Kim Kardashian was a Los Angeles housewife. In 2000, 20-year-old Kim married record producer Damon Thomas in a quickie Las Vegas wedding. After three years, the couple divorced but not before some nasty allegations. In divorce papers that were leaked in 2010, she accused Thomas of physical and emotional abuse. Thomas denied the allegations and accused his ex-wife, somewhat redundantly, of being "obsessed with fame.” He told InTouch weekly: “She can't write or sing or dance, so she does harmful things in order to validate herself in the media. That's a fame-whore to me. It's just not cool at all."

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In May 2010, Kim Kardashian learned the hard way not to mess with Beliebers. After jokingly tweeting that 16-year-old Justin Bieber was her boyfriend, 29-year-old Kim began receiving death threats. Ever the peacemaker, Bieber tried to quell the situation: "ladies calm down," he tweeted, adding that Kardashian was only "a friend—a very sexy friend but a friend. no need 4 threats.” A few months later, the controversy reignited when the two were spotted holding hands on the beach together. Turns out the photos were just for an Elle fashion shoot. And, yes, even an “ex” like Bieber has been invited to Kim’s big day on Saturday.

Kevin Mazur