Never say never. After years of vehemently denying that he'd ever get married again, news broke this weekend that George Clooney is in fact engaged to his girlfriend, Amal Alamuddin. What will Hollywood do now that its most eligible bachelor is finally off the market? And how does his whirlwind love story compare with those of Adam Levine and Matthew McConaughey, two other notorious playboys gone good? Let's find out!
His previous stance on marriage: Just three years ago, Piers Morgan grilled Clooney on how he felt about his parents' 50-plus year marriage. In response, Clooney revealed his philosophy on relationships: "I hate to blow your whole news story, but I was married, so I gave it a shot," Clooney said of his four-year union with actress Talia Balsam, whom he divorced in 1993. He went on to explain that his first and only marriage should have "proven how good I was at it."
In fact, he even wrote an essay for Esquire in 2011 that touched on the marriage subject. "People forget that I was married. I love that, 'Will he get married?' I don't talk about it because I don't think about it. I don't ever question other peoples' versions of how they live their lives or what they do," he wrote. "I understand that it's a subject of interest for people. But sometimes it exists only because it came up years ago. It becomes this conversation piece that constantly resurfaces."
His relationships: Clooney seemed more than content toting his gorgeous string of ladies (from Sarah Larson and Elisabetta Canalis to most recently Stacy Keibler) to his Lake Como and Cabo San Lucas vacation homes. All of the women made a point of agreeing to his no-marriage policy, at least while dating.
What happened: He met his match! The stunning British lawyer seems to have everything he was looking for, which perhaps explains his previous hesitations. "It's actually not that surprising. He likes a woman with brains and class," a source told Us Weekly of the engagement. "She's the full package. His first wife Talia came from a good family and was very smart herself. He's happy and found his ideal match. He didn't settle, so good for him."
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His previous stance on marriage: The hunky Maroon 5 singer and The Voice judge used to use his fame as a soapbox for philosophizing on love. "I don't know if it's possible to live the rock 'n' roll lifestyle and still be romantic," he once said in reference to his dating history. As a rock star, he likely grappled with these feelings often, especially when it came to fidelity. "Instinctively, monogamy is not in our genetic makeup," he said at another point.
But he wasn't categorically opposed to marriage; in reality, it was quite the opposite. "I'm extremely fascinated by marriage," he said. "I want to study marriage. I want to learn about it. I want to know it. I want to figure out whether or not I want to do it. I'm not just going to leap into it, because that's not good for anybody." It seems that he, like Clooney, was waiting for the right woman at the right time.
His relationships: Remember when Levine rivaled Leonardo DiCaprio in his modelizing ways? Aside from the titular girl he dated who inspired Maroon 5's breakout album "Songs About Jane," he romanced many models, including Nina Agdal and Victoria's Secret Angel Anne V. Somewhat awkwardly, he began dating his now-fiancée mere months after he strutted the stage with her fellow Angel during the Victoria's Secret Fashion Show. Though he wisely didn't attend the next year's show, he seemed unbothered by publicly dating women who were colleagues.
What happened: He met Behati Prinsloo. The Namibian stunner dated Levine for about six months before they broke up, only to get back together when Levine realized how much he missed her. Mere weeks after they reunited, he proposed. Since then, he's been open about his change of heart. "Famous last words, 'I'll never get married,'" Levine told Jay Leno in October. "I still don't necessarily think you have to get married unless you meet someone that makes you want to marry them. And then you marry them and it's wonderful." Sounds like his "studying" worked out!
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His previous stance on marriage: Long before he settled down with now-wife Camila Alves, McConaughey let his lifestyle speak for itself. The Oscar winner was once arrested, lived out of a trailer, and seemed more than happy to never say I do. "I was a wild one until I met my wife," he once admitted. "I had some wonderful women in my life," he said in February of his dating history. "But I was in no rush. When I married I intended to stay married. I did not want to make a mistake." A perfectly laid-back attitude for a genuinely chilled-out guy.
His relationships: McConaughey enjoyed relationships with Sandra Bullock, Penelope Cruz, and other gorgeous ladies before meeting Alves at a Los Angeles bar in 2007. The two quickly became serious, and welcomed two children before finally tying the knot in June 2012.
What happened: Time caught up with him. "I could see my 40th birthday looming," he has said of his decision to get married. "I was an older bachelor than many of my friends. I enjoyed the life I was leading but knew it could not go on like that." And it seems his patience paid off. Throughout this awards season, the Dallas Buyers Club star praised and thanked his wife, who was constantly by his side. "I've got a wife who challenges me," he told Details. "There were two movies I wanted to do last year, but they were back-to-back with no separation. She was like, "You want to do it — buck up, grab your nuts, and make it happen. We'll be there with you."