Stacy Keibler, 2011-2013
Leggy—check. Blonde—check. Drop-dead gorgeous—check. Despite having all the prerequisites one needs to catch the eye of Clooney, the young starlet failed to lock it down. After a two-year courtship and numerous romantic getaways to George's Lake Cuomo digs, the pair called it quits.
Elisabetta Canalis, 2009-2011
After a two year stint on Clooney's arm, the Italian model ended their high-profile relationship. Even a common love for her mother country couldn't keep them together.
Sarah Larson, 2007-2008
Clooney swept the former Vegas cocktail waitress off her feet in 2007. The following year, she became the first girlfriend to ever accompany Clooney to the Oscars. Alas, the duo went their separate ways shortly after.
Lisa Snowdon, 2000-2005
In 2000, Clooney started an on-and-off relationship with the British model after meeting while filming a commercial in Spain. The couple officially ended things five years later, though they supposedly still keep in touch.
Talia Balsam, 1989-1993
Alamuddin won't be the first Mrs. Clooney. That honor goes to the actress (and current wife of Mad Men's John Slattery) who was married to the 52-year-old movie star for four years.
Kelly Preston, 1987-1989
Clooney and John Travolta's wife shared a home in the Hollywood Hills and, at one point, custody of a potbellied pig named Max.