If George Clooney were a woman, his lengthy dating history would have resulted in him being called some rather unflattering names, but since he’s a man, the worst people will call him is a “serial dater.” Here’s a list of every relationship (and alleged relationship) Clooney’s had since his arrival in Hollywood 30 years ago until his 2014 marriage to human rights lawyer Amal Alamuddin.
Dedee Pfeiffer
In the 1980s, Clooney dated Dedee Pfeiffer (yes, Michelle’s sister). Pfeiffer has had her own career in film and TV, appearing on Seinfeld,Friends, CSI: NY and other shows, but has since put acting aside to pursue a master’s degree in forensic psychology.
Kelly Preston
Clooney and Preston dated from 1987 to 1989, when they were 26 and 25, respectively. The two lived together while working on their respective careers (this was before Clooney joined the cast of ER), and Clooney even bought Preston a baby potbellied pig named Max, whom he kept after the couple broke up. Preston went on to appear in more than 60 films and television shows and to marry fellow actor John Travolta.
Talia Balsam
Balsam and Clooney married in Las Vegas in 1989 and divorced in 1993. “I probably — definitely — wasn’t someone who should have been married at that point,” Clooney said in a Vanity Fair interview. “I just don’t feel like I gave Talia a fair shot.” Balsam, whose film, stage and television career includes All the King’s Men, Taxi, Thirtysomething, The Good Wife and Mad Men, has been married to actor John Slattery since 1998.
Kimberly Russell
After his divorce from Balsam, Clooney had a three-year relationship with actress Kimberly Russell. He broke up with her via a “Dear Kim” letter (yikes). Russell is best known for her work on Head of the Class and Ghost Dad and has also appeared on ER, Family Matters and The Steve Harvey Show. She lives in Malibu with husband Michael Bonewitz, who she married in 2003.
Karen Duffy
Actress, author, model and former MTV VJ Duffy had a brief relationship with Clooney in 1995 and made many public appearances. The two remain close friends.
Celine Balitran
Clooney met French law student and waitress Celine Balitran while filming The Peacemaker in Paris in 1996. The two dated for three years. Balitran then married filmmaker David Rosenthal (from whom she is now divorced) and appeared on the French reality show La Ferme Célébritiés.
Lucy Liu
Liu and Clooney were rumored to be dating in 2000 while Liu’s fame was ascending due to her work in Charlie’s Angels. They were photographed kissing on New Year’s Eve in 2006.
Krista Allen
Allen, best known for Baywatch: Hawaii and Days of Our Lives, met Clooney on the set of Confessions of a Dangerous Mind, which Clooney directed and in which she had a small part. They dated from 2002 until 2004 and were last linked in 2008.
Lisa Snowdon
British model and television/radio presenter Snowdon met Clooney in 2000 when they worked together on an ad for Martini, an Italian vermouth. They had an on-and-off relationship until 2005, during which Clooney may or may not have dated Krista Allen. Snowdon hosted Britain’s Next Top Model as well as a popular radio show in England. “I’m always going to be George Clooney’s ex,” she told Daily Mirror in 2013. “I will have to do something super radical for people to forget about it.”
Renée Zellweger
When Clooney was asked if he had dated Zellweger, longtime friend and co-star in the 2008 film Leatherheads, Clooney replied, “A little bit.”
Sarah Larson
Larson, a former Fear Factor contestant, met Clooney in 2007 while cocktail waitressing in Las Vegas at the restaurant where Clooney’s film Ocean’s Thirteen premiered. The two broke up in 2008, but not before they were in a motorcycle accident together in New Jersey. Larson now lives in New York City, where she works as the director of a medical spa and teaches yoga.
Elisabetta Canalis
Italian actress, model, dancer and Goodwill Ambassador Canalis dated Clooney for two years before he allegedly ended it because Canalis was talking too much about the couple’s personal business. Both Clooney and Canalis were witnesses in the 2011 trial of former Italian Prime Minister Silvio Berlusconi. Post breakup, Canalis appeared on Dancing with the Stars and has since married and had a daughter.
Stacy Keibler
Apparently Clooney told Kiebler — an actress, model, dancer and retired professional wrestler — that he would marry her, but the couple broke up in 2013 after two years of dating. Kiebler married CEO Jared Pobre in 2014. They have one daughter.
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