These ladies somehow let George Clooney get away. We bet they’re regretting that a lot right now.
DeDee Pfeiffer
DeDee Pfeiffer dated Clooney in the early 1980s. He would then go on to star with her sister, Michelle Pfeiffer, in the 1996 movie One Fine Day.
Kelly Preston
Kelly Preston went on to marry John Travolta. But first she lived with Clooney in the late 1980s and even gifted him with a pig.
Talia Balsam
Talia Balsam actually married Clooney! But their relationship was over after four years and the split left a large scar on the actorâÂÂs heart.
Denise Crosby
Clooney admitted in an interview with Esquire that he has seen Denise Crosby, best known for her role on Star Trek The Next Generation, naked. In bed!
Kimberly Russell
Kimberly Russell went to bed with Clooney between 1993-1995. These two met on the set of a commercial shoot.
Karen Duffy
Karen Duffy, the former former MTV VJ, was Clooney’s date to the Emmy Awards in 1995. They are still good friends.
Celine Balitran
Celine Balitran was a French law student and waitress who hooked up with Clooney in 1996. HeâÂÂs always had a thing for accents.
Brooke Langton
Brooke Langton is best known for her role on Melrose Place. She got together with Clooney in 1999.
Traylor Howard
Traylor Howard starred on Two Guys, a Girl and a Pizza Place and Monk. She starred on ClooneyâÂÂs arm in 2000.
Lisa Snowdon
Lisa Snowdon is a British personality. She was on and off with Clooney for awhile in the mid-2000s.
Maria Bertrand
Clooney fell so head over heels for Maria Bertrand, a Canadian waitress, that he cast her in a small part in his directorial debut, Confessions of a Dangerous Mind.
Krista Allen
Krista Allen was also cast on Confessions of a Dangerous Mind. She dated Clooney in 2004 for a bit and then again in 2006.
Sarah Larson
Remember Sarah Larson? The former Fear Factor contestant and Vegas waitress got it on with Clooney between 2007-2008.
Elisabetta Canalis

Yup, another woman with an accent. Elisabetta Canalis turned her relationship with Clooney into a Dancing with the Stars contestant.
Stacy Keibler

We thought Stacy Keibler might get the marriage job done. But she’s gone off and had a baby with someone else, so everyone is now happy!