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The duo reportedly started dating after meeting on the set of the 2005 film Brick, but they only stayed together for six months.
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The Dawson's Creek alum and the Josie and the Pussycats star dated for about a year back in 2002.
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The man who now rocks the Iron Man suit for Marvel admitted that drugs and alcohol were to blame for the end of his seven-year relationship (1984 – 1991) with the Sex and the City star. "I liked to drink, and I had a drug problem, and that didn't jibe with Sarah Jessica," he admitted in an a 2008 interview with Parade, "because it is the furthest thing from what she is. She tried to help me. She was so miffed when I didn't get my act together."
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The Friends alum and The Hangover star supposedly had a fling 2003, but it didn't last long enough to be more than a little blip on the Hollywood hookup radar.
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In 1999, way before he wed Blake Lively, Reynolds dated the 3rd Rock From the Sun star. The duo even attended the premiere ofThe Green Mile together.
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The child actors turned A-listers briefly dated in 2006 but remained close friends—and co-starred in the intense 2009 dramaBrothers.
"She's a vegan," Gyllenhaal pointed out when presenting Portman with the Desert Palm Achievement Award in 2011, "which makes it really frustrating when you're picking a place to eat."
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Diaz and Dillon began dating in 1995, but broke up shortly after they wrapped filming on the 1998 comedy There's Something About Mary.
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Spade's dating roster reads like a who's who of hot Hollywood blondes: Heather Locklear, Nicollette Sheridan and Playboy Playmate Jillian Grace. In 2002, he added the Modern Family star to that list, but the couple called it quits after a year of dating.
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Before marrying Mila Kunis, Kutcher dated Jones from 1998 to 2001. And according to the Mad Men star, he was not a very good boyfriend at the time. "He was not supportive of my acting," Jones told GQ in 2009 . "He was like, 'I don't think you're going to be good at this.' So, f--k you!"
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The Friends alum dated Batman! The couple split in 1995 after over six years together, with Cox telling People shortly after the split, "It's the most important relationship I've ever had, and I think he's the most wonderful person I've ever met."
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The SNL alum and late night host was linked to Ryder in 2002, but she denied a hookup to W magazine , insisting that the two were "just friends."
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Before she married and three children with ex-husband Brian Austin Green, Fox dated the 7th Heaven star from 2003-2004. The Jennifer's Body actress is now engaged to Machine Gun Kelly.
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The Charmed actress and the singer dated briefly after he and Britney Spears broke up in 2002.
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The crooner calls his two-and-a-half year courtship with Jones from 2003 to 2006 his longest relationship ever. "We were madly in love. It was definitely my longest relationship," he told Details in 2013. "I'd love to get into another serious relationship. I am a real romantic at heart."