Stars Who Traded Down in Romance: Demi Moore, Jennifer Aniston, and More

After dating George Clooney, it’s all downhill. But Steve-O? From Demi Moore to Edward VII, celebs who aimed lower.

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After dating George Clooney, Elisabetta Canalis is now seeing Steve-O. See other celebrities who aimed lower, including Jennifer Aniston, John Edwards, and Madonna.

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Elisabetta Canalis

Admittedly, almost any man could seem like a step down once you’ve been involved with George Clooney, but going from a two-time Sexiest Man Alive to Jackass star Steve-O feels like a pretty precipitous drop for Elisabetta Canalis. Then again, perhaps Canalis (who dated Clooney for two years before their breakup in July  2011) has more in common with Steve-O—after all, they’re both former Dancing With the Stars contestants. So that’s something.

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Demi Moore

Three years after her divorce from Bruce Willis, Demi Moore met Ashton Kutcher at a party in Hollywood—and he snubbed her.  As Moore explained to Regis Philbin and Kelly Ripa in 2010, “The first night I met him he didn’t have two words to say to me—he had a singular focus and it was on somebody else.” After overcoming that false start, the two started dating and despite their 15-year age difference and his penchant for an open marriage, they remained a couple for six years. Still, die-hard Willis fans point out that it was Bruce who offered to help Demi recover at his home after she was taken to the hospital recently—while Ashton was off in Brazil, partying.

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Jesse James (Sandra Bullock for Kat Von D)

If you’re going to break up with America’s Sweetheart, you’d better at least have the good sense to find someone worthy of polishing her Oscar. But in 2010, when Jesse James cheated on Sandra Bullock with his tattooed Nazi-loving lover, Michelle “Bombshell” McGee, he lived up to his outlaw name. When asked why he did it, James told The Daily Beast:  “I think it was several factors: ego, loneliness, distrust, which probably led to resentment.” Meanwhile, adding to America’s resentment of James was the fact that months after splitting from Bullock, he became engaged to Inked star Kat Von D. "I feel like I'm the luckiest girl," she said at the time, adding, "I don't care what anyone thinks." Alas, they never made it down the aisle.

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Jennifer Aniston

Much like Life After Clooney, it’s hard to follow Brad Pitt. But when Pitt left his wife, Jennifer Aniston, for Angelina Jolie, she immediately found comfort in the arms of her co-star at the time, Vince Vaughn. Unfortunately the movie they were making, The Break-up, foretold their future as a couple. Then a few years after that, Aniston stepped further down the dating food chain when she got involved with John Mayer. While he no doubt thought her body was a wonderland, the couple’s on-and-off relationship ended in 2009 because of his Twitter addiction. Thankfully, she recovered and is now back in Sexiest Man Alive territory with actor Justin Theroux.

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David Arquette

In fairness to David Arquette, he always seemed a little out of his league when it came to Courteney Cox, a fact that wasn’t lost on the producers of the Scream series. The couple met on the set of the first movie in 1996, and their relationship on-screen mirrored it off-. Arquette’s hapless Dewey Riley eventually married Cox’s glamorous Gale Weathers, but by Scream 4, their fictional union was on the rocks, as it was in real life. The couple split in 2010 and after a stint in rehab, Arquette has been dating Christina McLarty, who was previously linked with Girls Gone Wild founder Joe Francis.

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John Edwards

Had former presidential candidate John Edwards simply read Jay McInerney’s novel Story of My Life, he would have known to stay away from documentary filmmaker Rielle Hunter while on the campaign trail. In that 1988 roman a clef, McInerney turned his ex-girlfriend, Hunter (then known as Lisa Druck) into Alison Poole, a coke-addicted nymphomaniac. But Edwards must have skipped that book because he had an affair with Hunter in 2008 and his cancer-stricken wife, Elizabeth, eventually divorced him when it was revealed that he had a love child with her. (And possibly a sex tape.) While Edwards is currently facing a trial for possible campaign violations, many still wonder if he will marry Hunter, who lives nearby. Or perhaps he can just obtain a doctor’s note to get out of it?

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Jennifer Lopez

Does this sound familiar? After breaking up with a music star (Sean Combs) in 2000, Jennifer Lopez had a relationship with one of her backup dancers (Cris Judd), whom she eventually married. After divorcing Judd in 2003, J. Lo took two steps up romantically—a relationship with Ben Affleck and another marriage, this time to Marc Anthony. But following her split from Anthony last July, Lopez is now dating—wait for it—a backup dancer. Twenty-four-year-old Casper Smart seems truly smitten with the 42-year-old American Idol judge—“Age, status, n opinions of others are irrelevant. Our hearts are endless and our souls infinite........... To be continued,” he tweeted recently—but Lopez still has great chemistry with Anthony on their new reality show, Q’Viva. "It's fun because we know each other so well, but it has its moments,” Lopez told David Letterman about working with Anthony now. “The same things that didn't really work ... sometimes come up."

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Ethan Hawke

When a man leaves his wife for their children’s nanny, he naturally opens himself up to some scorn. Five years into his marriage to actress Uma Thurman, Ethan Hawke reportedly had an affair with the Uma-esque Ryan Shawhughes, who looked after the couple’s two kids.  When a Daily News reporter likened Hawke’s relationship with Shawhughes—whom he married in 2008—to an affair Jude Law had with his children’s nanny, Hawke was not amused: "I don't know what the Jude Law comment was,” the actor responded, “I assume it was derogatory. But I'll tell you this: I liken my situation to The Sound of Music, not to Jude Law."

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During the 2011 Golden Globe Awards, host Ricky Gervais joked about the effects the recession was having on Hollywood. "Even Madonna has had to get rid of one of her personal assistants,” he said solemnly. “Our thoughts go out to you Guy Ritchie." But following end of their eight-year marriage, the director of Sherlock Holmes has moved on quite nicely—he and his girlfriend, model Jacqui Ainsley, just had a son in September—while Madge is back to playing with her boy toys. The 53-year-old Madonna is now seeing 24-year-old Brahim Zaibat.

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Edward VIII

Depending on your point of view, the relationship of Edward VIII and Wallis Simpson is one of the great love affairs of the 20th century or one of the most foolish. It’s certainly romantic to imagine abdicating the throne as king of England for the woman you love, but on the other hand, you’re the king of England. Their legendary relationship is the subject of Madonna’s new movie W./E. which opens this weekend, and the couple was also recently cited in the autobiography of Scotty Bowers, a former Marine who claimed to have set up gay and straight liaisons for countless old-time Hollywood stars. Among Bowers assertions—that he had threesomes with the Duke and Duchess of Windsor. “All of my famous tricks are dead by now,” Bowers wrote. “The truth can’t hurt them anymore.” Ah, romance.