After a short marriage with actress Talia Balsam (1989-1993), George Clooney vowed to stay a bachelor for the rest of his life. Many women tried to change his mind, but only British-Lebanese lawyer Amal Alamuddin managed to get him to commit to marriage again.

The two got married in Venice, with guests ranging from Bono to Anna Wintour. When the two got engaged in April, few thought the bachelor would actually settle down, especially since there’s a long line of women who thought they could change him and failed. Check out some of George Clooney’s famous former girlfriends.

Dedee Pfeiffer

Michelle Pfeiffer’s younger sister Dedee was one of the first actresses to date Clooney in the early 1980s. 

George Clooney With Dedee Pfeiffer

Things didn’t work out between the two, and Dedee Pfeiffer went on to get married three times, the final union with Irish actor Kevin J. Ryan ending in 2013.

Kelly Preston

George Clooney And Kelly Preston

The actor’s first high profile relationship was with Kelly Preston. She’s one of George Clooney’s famous former girlfriends because soon after breaking up with him she dated Charlie Sheen, before getting married with John Travolta in 1991. Clooney and Preston moved in together in 1988, but they couldn’t make it work in the long run.

Kimberly Russell

George Clooney And Kimberly Russell

The first woman to capture Clooney’s heart after his divorce from Talia Balsam was Kimberly Russell. After meeting on the set of a commercial, Russell and Clooney dated for three years. Unfortunately for the actress, Clooney’s divorce was still fresh and she had no chance of getting him to put a ring on it.

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Lucy Liu

George Clooney And Lucy Liu

With plenty of rumors about their relationship, both in 2000 and 2006, Lucy Liu might also be one of George Clooney’s famous former girlfriends. The two never acknowledged the relationship, but they did share a New Year’s kiss in 2006. Besides working in the same field, Liu also shared Clooney’s passion for championing human rights.

Renée Zellweger

George Clooney And Renee Zellweger

Another long time rumored girlfriend, Renée Zellweger kept dening any rumors about a relationship with Clooney, despite the actor saying that they dated “a little bit”. Rumors about their romance first surfaced in 2001, then came back in 2006, but if Clooney has a type, that’s certainly not A-list actresses.

Krista Allen

George Clooney And Krista Allen

After meeting on the set of “Confessions of a Dangerous Mind”, actress Krista Allen and the bachelor starting dating. She’s one of George Clooney’s famous former girlfriends because they had an on and off relationship until 2006. Their first split was in 2004, and they called it quits for good in 2006. Allen went on to marry British musician Mams Taylor in 2010, but divorced him two years later.

Lisa Snowdon

George Clooney And Lisa Snowdon

Another on and off girlfriend, British model Lisa Snowdon first started dating Clooney in 2001. The final breakup occurred in 2006. Snowdon also marked the end of the eligible bachelor’s string of romances with actresses. After moving on from Snowdon, the actor came back to dating waitresses, a trend he started in 1996 with Celine Balitran.

Sarah Larson

George Clooney And Sarah Larson

Even though she was a cocktail waitress when she met Clooney, Sarah Larson is one of George Clooney’s famous former girlfriends since her short relationship with the actor landed her on the cover of Harper’s Bazaar. She also accompanied him on the red carpet at the 2008 Oscars, where George has a chance to practice his tailoring skills by fixing a wardrobe emergency for her.

Elisabetta Canalis

George Clooney And Elisabetta Canalis

One of Clooney’s high profile relationships, Elisabetta Canalis met the actor in Italy. The Italian actress and TV host dated Clooney for two years, from 2009 to 2011. Even though she didn’t manage to walk down the aisle with Clooney, Canalis got married two weeks before the actor’s wedding to Amal Alamuddin.

Stacy Keibler

George Clooney And Stacy Keibler

The former professional wrestler is probably the unluckiest one of George Clooney’s famous former girlfriends. She almost managed to make him commit, but she still couldn’t convince him to put a ring on it. Keibler dated Clooney from 2011 to 2013, splitting up with him less than one year before he announced his engagement to Amal Alamuddin.