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HILARY DUFF, 22
Married to Mike Comrie: 2010-2014
After three years of dating, the actress and her former hockey player beau tied the knot in August 2010 during an intimate ceremony in Santa Barbara, Calif. Less than two years later, they welcomed son Luca, but by January 2014, their marriage was over. "They are dedicated to loving and parenting their amazing son, and ask for privacy at this time," said a rep for Duff.
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ASHLEE SIMPSON, 23
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BRITNEY SPEARS, 22
Married to Kevin Federline: 2004-2006
The pop princess pulled a fast one when she secretly walked down the aisle with Federline in September 2004 at an event attendees were told was an engagement party. Their union produced two sons, Sean Preston and Jayden James, but Spears called it quits in 2006, filing for divorce.
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CHRISTINA AGUILERA, 24
Married to Jordan Bratman: 2005-2010
The Voice judge was a blushing bride in white when she said to music executive Bratman in a sunset ceremony on Nov. 19, 2005. Less than three years later, the couple welcomed son Max, but parted ways in September 2010, with Aguilera telling PEOPLE, "Although Jordan and I are separated, our commitment to our son Max remains as strong as ever."
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SCARLETT JOHANSSON, 23
Married to Ryan Reynolds: 2008-2010
With only a handful of close friends and family in attendance, Johansson and Reynolds wed in Vancouver, Canada, in late September 2008, only four months after getting engaged. The dissolution of their marriage proved as quick as their courtship, with the pair announcing their decision to divorce in a joint statement. "We entered our relationship with love, and it's with love and kindness we leave it," it read.
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KATHARINE MCPHEE, 23
Married to Nick Cokas: 2008-present; separated
"[Nick] is the love of my life," McPhee gushed to PEOPLE when she tied the knot with the producer in 2008. But when the American Idol alum was caught kissing her former Smash director Michael Morris in October 2013, a source revealed that McPhee separated from her husband earlier in the year.
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ANGELINA JOLIE, 20
Married to Jonny Lee Miller: 1996-1997
Seven months after costaring in 1995 cyberpunk thriller Hackers, Jolie made her way down the aisle wearing black leather pants and a white top with the British actor's name scrawled on the back in her own blood. Jolie, now engaged to Brad Pitt, remained good friends with Miller even after their 1997 split.
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AVRIL LAVIGNE, 21
Married to Deryck Whibley: 2006-2009
Before finding perfect harmony with husband Chad Kroeger, the rocker wed the Sum 41 lead singer in a nondenominational outdoor ceremony in Montecito, Calif., on July 15, 2006. "I am grateful for our time together, and I am grateful and blessed for our remaining friendship," she said when the couple announced their separation in 2009.
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KHLOé KARDASHIAN, 25
Married to Lamar Odom: 2009-2013
Cameras rolled as Odom married into TV's biggest family following a blink-and-you-missed-it monthlong courtship. But by summer 2013, speculation swirled that Odom's substance-abuse issues put an irrevocable strain on their marriage. Kardashian filed for divorce just before the year ended, telling U.K. Cosmopolitan, "I need a good fresh start."