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George Clooney and accomplished barrister Alamuddin, who specializes in international law, human rights, extradition and criminal law, were first photographed stepping out in London in October 2013. They've since enjoyed romantic, globe-trotting jaunts, including a trip to Tanzania and a visit to the Seychelles. "It's like they want the people they love to know that this is real," a source told PEOPLE of their engagement, "that they plan on being together forever."
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Dated from 2011-2013
The former wrestler seemed to have what it takes to pin down the ultimate bachelor when their romance began heating up in the summer of 2011. "She's very tall. She can kick my ass," Clooney told E! News later that year, adding that Keibler's also a "nice girl." But after some cozy trips down the Oscars red carpet (and around the world!), news of their split broke on July 8. "She wants to have children and a family someday," a source tells PEOPLE. "She knows where George stands on that."
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Dated from 2009-2011
The Italian actress enjoyed life in the limelight with the two-time Sexiest Man Alive, taking strolls down the Academy Awards red carpet and jetting to Hawaii. "I love it," Canalis told PEOPLE of her romance with the Oscar winner. But two years after they first stepped out together as a couple at the Venice Film Festival, Clooney and Canalis announced the end of their romance on June 22. "We are not together anymore," they said in a joint statement. "It's very difficult and very personal, and we hope everyone can respect our privacy."
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Dated from 2007-2008
Clooney initially met the cocktail waitress at his birthday bash, where they "were dancing, taking pictures, being silly," Larson recalled of her first meeting with the A-lister before they became an item years later. The couple attended the Oscars together (pictured here) – a first for the actor, who had never taken a girlfriend to the Academy Awards – but broke up shortly afterward in May 2008.
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Dated on amp off since 2002
The Baywatch alum's rep said they were "just friends" after they were spotted getting cozy in 2002 – the same year Allen appeared in Clooney's directorial debut, Confessions of a Dangerous Mind – and dated on and off until 2008.
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Dated on and off since 2000
After hitting it off while taping a TV commercial in Spain, Clooney and the British model began dating on and off in 2000. The couple walked the red carpet together at the Los Angeles premiere of The Bourne Supremacy (pictured here) in July 2004, and were last spotted together in November 2005 at a London party, although they were not dating at the time.
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Dated from 1996 to 1999
Clooney met the waitress in Paris while filming The Peacemaker in 1996. The French law student followed him to L.A., where the two savored the mornings they "wake up in each other's arms," Balitran told PEOPLE. But the wake-up call came in 1999, when the actor broke up with Balitran to go back to his bachelor lifestyle.
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KAREN 'DUFF' DUFFY
Dated in 1995
The former MTV VJ was Clooney's date to the 1995 Emmy Awards (pictured here). Although their relationship was short-lived, there seemed to be no hard feelings after it ended: Duffy set sail with Clooney and then-girlfriend Canalis on a Lake Como boat trip during the summer of 2010. "George, you know, he's very loyal," she told PEOPLE of their enduring friendship.
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Dated from 1987 to 1989
The couple moved in together in 1988, sharing their Hollywood Hills home with their pet potbellied piglet, Max. "He's got a great bod," Preston joked to PEOPLE about her attraction to the charmer. When the two broke up in 1989, the actor continued to raise Max solo until the pet went to hog heaven in 2006.
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Dated in 1984; Married in 1989 to 1992
Just months after ending his relationship with Preston in 1989, Clooney and Balsam, whom he briefly dated in 1984, tied the knot in Las Vegas. "I probably – definitely – wasn't someone who should have been married at the point," he later reflected. "I just don't feel like I gave Talia a fair shot." Will Clooney ever settle down? Stay tuned....