Celebrity Couples From the Past They Dated?! Celebrity Couples From the Past! February 13, 2013 Share This link Celebrity Couples From the Past Source: Getty 7 / 69 by Lauren Turner 13 Save 0 Favorite 0 Cindy and Richard Cindy Crawford and Richard Gere were married from 1991 to 1995. More Photos Previous 7 / 69 Next by Lauren Turner 13 What’s Your Reaction? 0 0 0 0 0 0 Cindy and Richard Cindy Crawford and Richard Gere were married from 1991 to 1995. More Photos ‹ Back to Homepage Save 0 Favorite 0 Follow POPSUGAR Celebrity Pinterest Twitter Google + Instagram Featured Partners The Wanted's Siva Kaneswaran Is Engaged Sarah Palin to Host Outdoors TV Show Ben Affleck: Jennifer Garner Is the Most Important Person to Me Garth Brooks Announces World Tour More News at PEOPLE.com Simon Cowell Organized Baby Shower for Pregnant Girlfriend Lauren Silverman: All the Details! 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Create one now! ewalsh 42 weeks Great blast from the past. Juiceee 1 year I had no idea January Jones and Josh Groban ever dated. annie6417 1 year OMG!!! It's so funny and wierd as well, especially to see Brad Pitt, Matt Dammon and Heath Ledger...!!! kimmieb124 1 year I actually thought Katie Holmes and Chris Klein were a good match. Much more appropriate for who she was up until Tom Cruise came into the picture. They seemed sweet together. But Christina Applegate and Brad Pitt??? What? I missed that one. curLRocker 1 year Alanis and Ryan?! Mind BLOWN. chocolate79 1 year some of this is just very funny.... matt damon and winnona ryder! ha.. that's old school jmhendricks88 1 year I used to love Jake Gyllenhaal and Kirsten Dunst together. They were so cute! popfaninMD 1 year ahhhhhhh. Popsugar is going THERE....LOL...Madonna and Sean Penn, Crusise and Cruz....Ahhh what could have been. I'm particularly fascinated you included Garner and Varten. I thought was buried in a vault some where. LOL noonehere 1 year Colin and Busy??? ah ah ah! (terrible 90's or early 00's) ModernGraceKelly 1 year I remember Sandra and Ryan, because they did a movie together. He seems to date his leading ladies. I knew most of them, but some surprised me. I had no idea Edward Norton was engaged to Courtney Love. I just thought they went on a few dates. dreamalittledream 1 year wow brad really takes on the style of whoever he's dating! He and Gwyneth look like twins!!! (Whether he's dressing like Gwyneth, a California/beach style or motorcycle man, he always looks good though!) Allie Merriam 1 year Each couple is more surprising than the last! Anna Monette Roberts 1 year Really funny and freaky! 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