After his first marriage from 1989-1993 to actress Talia Balsam-- best known as Donald Sterling's ex-wife on Mad Men and John Slattery's wife in real life-- Clooney has been playing the field for over two decades.
Now that the once-hailed "eternal bachelor" is about to say those "I dos," let's look back at all the times the 53-year-old actor implied that he was NOT the marrying type.
1. As recently as Jan. 2014, Clooney was touting at a Monuments Men press event that he was staying a bachelor. "This fascination with my love life is really something," the Express UK reported. "I keep saying I'll never get married again or have children but people just don't want to believe me."
2. Okay, this isn't a direct quote from the actor, but it sounds like he owes his One Fine Day co-star a large sum of money. In October 2007, Michelle Pfeiffer told British TV host Jonathan Ross that she bet Clooney that he would tie the knot ...one day. "I bet him he would get married and he keeps inflating the bet - from $100 to $100,000. ...I still think he will, he's a handsome devil."
5. When he was votedPeople magazine's 2006 Sexiest Man Alive, he didn't say he wouldn't get married, but he certainly didn't seem in any rush to get to the altar. "Marriage? Who knows? I've been married. It's not something I'm looking out for. Things could always change, but it's not a consideration right now. The truth is I'm really happy. The things that are a drag in my life are so outweighed by the things that are great. I have families that I spend my days with, and friends I spend my days with, and people I care very much about. I get to do what almost no one gets to do. My life's really good."
6. During a CNN interview with Piers Morgan in Jan. 2011, he joked, "I hate to blow your whole news story, but I was married. Yeah, so I've proven how good I was at it, and I just ...I'm allowed one."
7. Again in Jan. 2014, he told Esquire magazine in regards to marriage and kids, "I haven't had aspirations in that way, ever. I was married in 1989. I wasn't very good at it. I was quoted as saying I'll never get married again pretty much right after I got divorced and then I've never talked about it since."
Never say never, Clooney.