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As the reality star files for her second divorce, look back at her past relationships

Shaun Harrison
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1 of 9 Michael Jaworski/FilmMagic.com

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Kim Kardashian and Kanye West are reportedly getting married in Florence on May 24. But it's been a long road. From sex tapes to 72-day marriages, look back at Kardashian's timeline of men.
2 of 9 Albert L. Ortega/WireImage.com; Frazer Harrison/Getty Images

Damon Thomas, 2000-04

Kardashian wed Thomas, a music producer, when she was 19 in 2000; the duo split four years later. Kardashian later alleged abuse, but she rarely acknowledges the union to this day. Kris Humphries was shocked — shocked, we tell you! — to learn that she was previously married during a family vacation in Bora Bora, so much so that her clan chastised her for not telling him.
3 of 9 John Shearer/WireImage.com

Ray J, 2004-2006

Kardashian had a serious relationship with Brandy's lil' bro that ended with a nasty breakup and the leak of their sex tape, making her the household name we know today.
4 of 9 Joey Foley/WireImage.com

Nick Lachey, 2006

Kardashian and Lachey had a brief fling in 2006, shortly after he split from wife Jessica Simpson.
5 of 9 Lester Cohen/WireImage.com

Reggie Bush, 2007-2010

Kardashian had an on-and-off relationship with the former New Orleans Saints running back for three years and was in the crowd when the Saints won the Super Bowl in 2010.
6 of 9 Chris Gallay/Getty Images

Miles Austin, 2010

After her split from Bush, Kardashian stayed within the NFL, dating the Dallas Cowboys wide receiver for a few months.
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Gabriel Aubry, 2010

Kardashian had a brief fling with Halle Berry's ex in late fall 2010 when the duo were photographed going on a few dates.
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Kris Humprhies, 2010-2011

Kardashian and Humphries started dating in December 2010 and got engaged in May. They married in August in a lavish ceremony that reportedly cost $20 million and aired as a four-part special on E! Three weeks after the special aired, Kardashian filed for divorce after 72 days.
9 of 9 Michael Jaworski/FilmMagic.com

Kanye West, 2012-present

Kardashian and West made their relationship official in April 2012. West has appeared on her E! reality show Keeping Up with the Kardashians and he even rapped about falling in love with her in his song "Theraflu." West announced that they were expecting a child during a concert on Dec. 30.