Dedee Pfeiffer (01 of13)
Open Image ModalKelly Preston (02 of13)
Open Image ModalGeorge Clooney moved in with girlfriend Kelly Preston in 1988 when they were both just starting out. Preston, who was the recipient of Max the pig from Clooney, also dated Charlie Sheen before marrying John Travolta in 1991. They have two children, after losing their son Jett in 2009. (credit:Getty)
Talia Balsam(03 of13)
Open Image ModalAfter he broke up with Kelly Preston, Clooney began dating actress Talia Balsam, whom he married in Las Vegas in 1989 and divorced three years later. Balsam is now married to John Slattery, with whom she's appeared on Mad Men. (credit:Getty)
Kimberly Russell(04 of13)
Open Image ModalShortly after his divorce, Clooney began a three-year relationship with actress Kimberly Russell, whom he met on the set of a martini commercial. More recently, Russell was seen in Lee Daniels' "Precious" and the forthcoming "Spychosis." (credit:Getty)
Karen Duffy (05 of13)
Open Image ModalGeorge Clooney and Karen Duffy were rumored to be dating when they appeared together at the Emmys in 1995. The same year, she was diagnosed with the relatively rare disease sarcoidosis, which she wrote about in her 2000 autobiography "Model Patient: My Life As an Incurable Wise-Ass."She continued to model for Revlon, and is married to John Lambros with a son. (credit:Getty)
Celine Balitran(06 of13)
Open Image ModalClooney met Celine Balitran in Paris while filming the movie "The Peacemaker" in 1996 and dated until 1999. She continued to work as a model, and was married for two years to filmmaker David Rosenthal, but divorced in 2004. (credit:Getty)
Lucy Liu(07 of13)
Open Image ModalClooney and actress Lucy Lui were rumored to be dating in 2000, and later the two were caught by paparazzi sharing a New Year's Eve kiss in 2006.Liu's career has branched out beyond the big screen, and the actress has devoted huge efforts to charity and working for human rights. (credit:Getty)
Krista Allen(08 of13)
Open Image ModalIn 2002 Clooney began dating actress Krista Allen, whom he met on the set of "Confessions of a Dangerous Mind." They broke up in 2004, reconciled briefly and broke up for good in 2006. In 2010, she married British musician Mams Taylor, but they separated in August 2011. Krista runs a blog called Veggie Boom Boom. (credit:Getty)
Lisa Snowdon (09 of13)
Open Image ModalClooney dated model Lisa Snowdon on and off for five years, before they finally ended it for good in 2006. Snowden is now a regular DJ for Capital Radio in London. (credit:Getty)
Renee Zellweger (10 of13)
Open Image ModalActress Renee Zellweger has been linked to Clooney a number of times. The pair were first rumored to have dated in late 2001, just before he started bumpy romance with Krista Allen, and again in 2006 the two were said to be together briefly. But in 2007 they denied there was ever a romance and said that they've been just friends for over a decade. (credit:Getty)
Sarah Larson (11 of13)
Open Image ModalWhile they were together for less than a year, Clooney dated Sarah Larson, a cocktail waitress from Las Vegas, and got lots of attention for doing so. They called it off in 2008. (credit:Getty)
Elisabetta Canalis(12 of13)
Open Image ModalGeorge Clooney and Elisabetta Canalis confirmed they were dating after Elisabetta was first spotted on the back of George's motorcycle in July 2009. The two dated for just under two years, breaking up in June 2011.She went on to contend in "Dancing With the Stars" and continued to model and perform. (credit:Getty)
Stacy Keibler(13 of13)
Open Image ModalClooney ended things with Stacy Keibler, a former professional wrestler and "Dancing With the Stars" contestant in July 2013 after two years of dating.Stacy, a former wrestler, has a new lifestyle show, "Supermarket Superstar," lined up for Lifetime channel. (credit:Getty)