1. Hugh Hefner and Crystal Harris

Hugh Hefner tweeted Tuesday that “the wedding is off. Crystal has had a change of heart.” Sources said Hefner, 85, and Crystal Harris, 25, supposedly had a “nasty argument” over the weekend, and Harris moved her things out of the Playboy mansion pretty much immediately—only a week before the wedding.
2. Gwyneth Paltrow and Brad Pitt

Paltrow stated she was too young for the commitment. “My internal stuff really tripped up and I felt really responsible and also like I was the architect of my own misery and I just made a big mess of it and…I was very upset for a long, long time about it,” she said. The broken engagement, she said, was responsible for her later relationship with a man she called a “total knucklehead,” although she refused to name names.
3. Julia Roberts and Kiefer Sutherland
She broke up with Sutherland just three days before the ceremony. Then she ran off with Sutherland’s best friend, actor Jason Patric. More than a decade later, he said, “I commend Julia for seeing how young and silly we were, even as painful and difficult as it was.”
4. Ben Affleck and Jennifer Lopez
Dubbed “Bennifer” by the press, “I don’t think I’ve ever been heartbroken in that way before—had so many hopes and dreams on something,” Lopez said after rumors seeped out about Affleck’s having a “wild night of sex” with a Canadian stripper at a party at Christian Slater’s house.
5. Katie Holmes and Chris Klein
Only weeks after they broke up, Holmes made her first public appearance with Tom Cruise at the David di Donatello Awards in Italy, with Cruise saying he was “beyond enamored.” Only three months after her breakup with Klein, Holmes and Cruise were engaged.
6. Alec Baldwin and Janine Turner
Turner said she was so broke she was “trying to hock” her engagement ring from Baldwin to pay her rent. Baldwin and Turner could not have gone in more opposite directions. Turner said she began to get “blackout drunk” and that “the devil was trying to get me down."
7. Carson Daly and Tara Reid
Not necessarily a recipe for marital bliss, Tara said later, "if I had married Carson, I’d probably have kids by now…I wouldn’t have had all that crazy partying. My life would have been completely different.’ But you know what? If it was meant to happen, it would have…but I’ve never loved anyone the way I’ve loved him.”
8. Demi Moore and Emilio Estevez
“She and I have seen each other socially over the years,” Estevez told People magazine. “But to work with her, man, was old home week.” Though they’ve since each been married and divorced (the second for Moore and the first for Estevez), Moore is head-over-heels in Twitter-advertised wedded bliss with Ashton Kutcher
9. Lance Armstrong and Sheryl Crow
“She wanted marriage, she wanted children; and not that I didn’t want that, but I didn’t want that at that time because I had just gotten out of a marriage, I’d just had kids,” Armstrong wrote in his 2009 book Lance.
Since then, Crow battled breast cancer and adopted two boys. Armstrong also added two more children to his brood, having a son and a daughter with girlfriend Anna Hansen.




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