Damon met Barroso, then a bartender at Miami’s Crobar, when he was in town filming Stuck on You. After a long day of shooting, some crew members invited Damon to get a drink. “They said, ‘Come on,’ and kind of dragged me along,” Damon told Ellen DeGeneres in 2011. “I literally saw her across a crowded room and eight years and four kids later, that’s my life. I don’t know how else our paths would have crossed if that didn’t happen.” The moral of the story? “When you’re tired, suck it up and go to the bar and you might meet your wife,” says Damon. The couple renewed their marriage vows in April 2013 with a small sunset ceremony in St. Lucia.
Jon Stewart and Tracey McShane
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Stewart met McShane, who was then a veterinary technician, on a blind date at a Mexican restaurant in 1996, just one month after Stewart was fired from his show on MTV. “It’s a fairy tale from my end,” McShane later told Oprah. “I had just gotten out of a seven-year relationship. I was depressed, and my friends were trying to set me up all the time. After a bad date, they’d ask, ‘What are you looking for?’ I had discovered The Jon Stewart Show, so I said, ‘Someone funny and sweet, like Jon Stewart.’” As fate would have it, McShane’s roommate at the time was working as a production assistant on the 1997 rom-com Wishful Thinking and played matchmaker when Stewart stopped by the set. In February 1999, Stewart proposed to McShane through The New York Times, having enlisted the newspaper’s crossword puzzle editor for help. (Among the clues specific to the couple? The answers to “Valentine’s Day Request” and “Recipient of the Request” were “Will You Marry Me” and “Tracey.”)
Jerry Seinfeld and Jessica Sklar
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