Hugh Hefner's Broken Crystal Harris Engagement, More Stars Who Got Jilted

Hugh Hefner says his wedding to Crystal Harris is off—five days before the ceremony. From Julia Roberts to Bennifer, see other stars who broke engagements.

Rex Features

Rex Features

Hugh Hefner and Crystal Harris

It’s only fitting that if the engagement is announced over Twitter, the breakup should also be announced over Twitter. 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. The ceremony was also scheduled to air on Lifetime on July 13. Although Hefner tweeted that Harris took their dog, Charlie, with her when she left, he seemed to be taking the breakup in stride, tweeting, “Since we’re not getting married on Saturday, I’ve scheduled a movie: ‘Runaway Bride.’ Seems appropriate.” Maybe he’s already found some outside comfort: One of the “Girls Next Door,” Bridget Marquardt also came over to “give her loving support.”

KEVORK DJANSEZIAN

Gwyneth Paltrow and Brad Pitt

Gwyneth Paltrow was just at the beginning of her career when she and Brad Pitt announced their engagement in 1993. The pair met when she was just 21 and cast as Pitt’s doomed wife in Se7en. Pitt, 31, was already a superstar. Paltrow said she resisted his advances at first because she thought” “Are you insane? You can’t get a crush on Brad Pitt!” He proposed after two years, when she went to visit him on the set of Seven Years in Tibet. They both talked about how excited they were to get married, with Pitt telling Rolling Stone magazine, “I can’t wait man…walk down the aisle, wear the ring, kiss the bride. Oh, man, it’s going to be great.” They were planning to get married in the summer of 1997, but the engagement was mysteriously broken off in June. Although at the time, most pointed fingers at Pitt—with one friend even saying, “He changed his mind a month ago”—Paltrow later said 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.

MARK J. TERRILL

Julia Roberts and Kiefer Sutherland

Julia Roberts’ acting in Runaway Bride certainly didn’t come out of nowhere. In 1991, the Julia Roberts-Kiefer Sutherland wedding had all the making of Hollywood royalty—and was even set to take place at 20th Century Fox’s Soundstage 14. But it was not meant to be. Roberts shocked the world when she broke up with Sutherland just three days before the ceremony. Then she ran off with Sutherland’s best friend, actor Jason Patric. Friends said Sutherland was “shocked” by the split, but 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.” Forgiving his former best friend was not so easy, however. “I’m surprised I never got a call from him saying I’ve fallen in love, da-da-da. Instead I found out from a stranger,” Sutherland said. Patric, for his part, called Roberts “trouble” and said she was “a person who very much put herself in the public eye, and the public life. I think everybody has the right to privacy, but once you use your personal life to advance your fame, you don’t really have the right to say no [to the press].” Patric and Sutherland eventually made up when they co-starred in the Broadway play The Championship Season, directed by Patric’s father, Jason Miller. “We had drinks last night and he said that was one of the best summers of his life when we did The Lost Boys,” Patric said in 2011. As for being a homewrecker? Said Patric: “They had a relationship that ended and then I was with her for a little while and it ended. They’ve both subsequently been married several times and I think they’re fine.”

RENE MACURA

Ben Affleck and Jennifer Lopez

In retrospect, it really doesn’t seem like there was any way for Ben Affleck and Jennifer Lopez to survive as a couple. Dubbed “Bennifer” by the press, Affleck and Lopez were opposites who had everyone paying attention—especially when he proposed with a $1.2 million, 6.1 carat pink diamond. They set the wedding date for September 14, 2003. The relationship caused even more frenzy when they starred in Gigli and gave an interview in a prime-time special with Diane Sawyer. But the movie bombed, and rumors seeped out about Affleck’s drinking and partying, and eventually he was accused of having a “wild night of sex” with a Canadian stripper at a party at Christian Slater’s house. The speculation was never confirmed, but the engagement was called off shortly thereafter. Both Lopez and Affleck said the relationship could never stand the constant media attention they were under. “I don’t think I’ve ever been heartbroken in that way before—had so many hopes and dreams on something,” Lopez said. “When you go through that kind of heartbreak in front of everybody, you are not quite the same person you were before.” Affleck, for his part, said they were “caught in the eye of the storm,” but later admitted the high-profile relationship—and breakup—was “probably bad for my career.” Affleck’s best friend, Matt Damon, later said Bennifer was “one of those weird situations where there was absolutely nothing you could do…all you could do is support [your friend] and talk shit about the people writing those things.” Despite all the pain, Affleck and Lopez seem to be doing fine now. Affleck married actress Jennifer Garner in 2005 and they have two daughters, Violet, 5, and Seraphina, 2. Lopez married singer Marc Anthony in 2004—only months after she and Affleck broke up—and now is the mother to twins Emme and Max, 3.

JENNIFER GRAYLOCK

Katie Holmes and Chris Klein

Long before Tom Cruise, Katie Cruise had a far lower-profile relationship with fellow actor Chris Klein. Together for five years in their early 20s, they broke up in 2005. Klein said later: “We grew up. The fantasy was over, and reality set in. We weren’t lighting each other’s fire anymore.” Before the split, they both admitted they spent much of their relationship apart. Klein, then the rising star of the American Pie movies, lived in Los Angeles while Holmes was filming Dawson’s Creek in Wilmington, N.C. But maybe there was something else at play? Only weeks after they broke up, Holmes made her first public appearance with Cruise at the David di Donatello Awards in Italy, with Cruise saying he was “beyond enamored.” By June 2005, only three months after her breakup with Klein, Holmes and Cruise were engaged after he proposed atop the Eiffel Tower, and she gave birth to daughter Suri in April 2006. Klein, meanwhile, had his second arrest for drunk driving in 2010, forcing him to check into rehab.

Peter Kramer

Alec Baldwin and Janine Turner

The liberal Baldwin and conservative Christian actress Janine Turner were engaged in 1983, when they were both in their 20s and struggling to break out into show business. Turner said later, “When I met Alec, I was 20. We got engaged. It was rushed, and it didn’t work. Alec taught me a lot about my emotions, about my childhood.” When Turner got her breakout role as Maggie in Northern Exposure in 1991, she said she was so broke she was “trying to hock” her engagement ring from Baldwin to pay her rent. Since the engagement ended, 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”; she stopped drinking at 23. Despite high-profile exes like Baldwin, Mikhail Baryshnikov, and Sylvester Stallone, Turner now lives a quiet life on a farm as a single mom to daughter Juliette. Baldwin, meanwhile, rocketed to fame in the 1990s, later marrying actress Kim Basinger and undergoing one of the messiest, high-profile divorces of all time. But perhaps their biggest difference is their political views: Baldwin is a staunch supporter of Democrats and President Obama, and is even rumored to be considering a bid for the Democratic nomination for New York City mayor, while Turner spoke at Tea Party summit in 2010, saying Obama and the Democrats “don’t want our children to know about their rights. They don’t want our children to know about a God!”

Chris Weeks

Carson Daly and Tara Reid

They were a match made in MTV heaven—not necessarily a recipe for marital bliss. Carson Daly and Tara Reid dated for 17 months and had gotten engaged in 2000, but the first sign of trouble came when they pushed back their summer 2001 nuptials. By July, they announced they had split. Reid said later, “I think, ‘well yeah, 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.” Daly, for his part, said of Reid: “We don’t really run in the same circles. But when we do run into each other, it’s always great to see her, and it’s always pleasant.”

Ron Galella

Demi Moore and Emilio Estevez

In 1985, divorcee Demi Moore and her massive crimped hair joined “The Brat Pack” in St. Elmo’s Fire, which co-starred Emilio Estevez. Soon enough, the two—who didn’t play love interests on-screen—found sparks off-screen. They apparently enjoyed being together so much that they got engaged, and in 1986, he directed his then fiancée in Wisdom. But the fireworks fizzled, and the engagement was called off. Though they’ve since each been married and divorced (the second for Moore and the first for Estevez), he is now engaged to writer Sonja Magdevski and Moore is head-over-heels in Twitter-advertised wedded bliss with Ashton Kutcher. Estevez found himself working with his former fiancée and her current husband on Bobby, which he wrote, directed, and starred in. “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.”

Lance Armstrong and Sheryl Crow

Shortly after filing for divorce from his first wife in September 2003, Tour de France champion Lance Armstrong began dating songstress Sheryl Crow. The couple announced their engagement in September 2005, but by February 2006, they revealed they would not to make the trek down the aisle. “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. Even though the couple underwent counseling, they couldn’t make it work. “We were at different points in our lives. We were not compatible on that issue,” he explained. 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.

Paul Sancya

Bristol Palin and Levi Johnston

Being a teen mom and the daughter of the vice presidential candidate in 2008 didn’t make things easy for Bristol Palin. Her high school boyfriend-turned-fiancé and the father of her son, Levi Johnston, said he planned to wed Bristol, baby Tripp notwithstanding. “We were planning on getting married a long time ago with or without the kid,” the teen father told the Associated Press. “That was the plan from the start.” But shortly after her mother lost the election, Palin also lost Johnston. The engagement was called off in March 2009 and an ugly custody and child support case ensued. Despite the public feuding and some Playgirl modeling, the couple kissed and made up in July 2010, announcing their engagement was back on. “It felt right, even though we don’t have the approval of our parents,” then 19-year-old Palin told Us Weekly. But three weeks later, the rings were off and the claws were back out. “I got played,” she told People. Palin also got a spot on Dancing With the Stars, her own reality show, and much more; all Johnston got was this lousy book deal.