For many years, George Clooney was Hollywood’s eternal Bachelor. He had been linked to many women over the years, before finally settling down into marriage and family life with Oscar winner and human rights lawyer Amal Clooney. While many may forget, Clooney did get married once to Talia Balsam, but the two divorced three years later. He went on to continue to have high-profile relationships with a long list of stars, but everything changed when he met Amal in 2013. If you’re a fan of George Clooney, follow along as we retrace a timeline of his famous flings:
While they were both struggling actors, George Clooney and girlfriend Kelly Preston moved in together in 1999. At the time, Clooney was starring in the sitcom, Roseanne, while Kelly was starring in her hit films Twins and Space Camp. The couple reportedly met when they were both invited to the same party by their agent. Clooney once shared that “the most important thing in my life is my relationship with Kelly.” The two dated from 1987 to 1989 and reportedly shared a pet pig. Preston passed in July 2020 following a battle with breast cancer.
One relationship of Clooney’s that many forget about is his first marriage to Talia Balsam. The two wed in Vegas in 1989, but divorced three years later in September. Balsam is now married to actor John Slattery. Clooney opened up to Vanity Fair in December 1996 about the relationship: “I probably, definitely, wasn’t someone who should have been married at that point. I just don’t feel like I gave Talia a fair shot. I was responsible for the failure of that marriage.”
Following his divorce from Balsam, Clooney entered into a three-year relationship with Kimberly Russell. The duo reportedly met on the set of a martini commercial. The couple called it quits in 1995 when Clooney moved on. It’s been reported that Clooney broke up with Russell through a letter. After the split, Kimberley opened up the relationship and shared: ‘You have to enjoy the ride while it lasts — he’s simply not the marrying kind. The guy is an absolute charmer, but just don’t mention the words “’marriage, commitment or babies.'”
Following this relationship, Clooney moved on to Celine Balitran, a French law student, who he met while filming The Peacemaker in Paris in 1996. Balitran followed Clooney to L.A. and the duo continued to date until 1999 before eventually calling it quits. In 2007, Clooney opened up about the relationship to Esquire and admitted the failure of the relationship was due to his fear of intimacy. “I was in a three-year relationship with this girl, Celine, who I really adored. A great girl. The truth is, it just became tougher and tougher for us to make it,” he shared at the time.
Soap opera actress Krista Allen dated George Clooney after she was cast in 2002’s Confessions of a Dangerous Mind. The duo dated until 2004 until Allen broke it off and Clooney began dating Lisa Snowdon. Clooney and Allen reportedly did reconcile briefly, but eventually called it quits for good in 2006. At the time, a friend close to the pair shared, “Krista has always been there for him. She admits she just can’t get over him. … George really loves her [too].”
Clooney began dating model and TV personality Lisa Snowdon in 2000. The couple had an on-and-off relationship for five years, before eventually ending the relationship for good in 2006. Lisa blamed the actor’s fame for interrupting her work, and ultimately their romance. “We [broke up] three years ago, but I still get asked about it a lot,” Snowdon told the Daily Mail in 2008. “The media attention when we were together was unbelievable.”
It’s been rumored that George Clooney and Renee Zellweger have dated on-and-off over the years. The two starred in the film Leatherheads together. Clooney and Zellweger were first linked in early 2001, before Clooney was with Krista Allen. They were suspected to be together again in 2006, but by 2007, Clooney and Zellweger denied the romance and claimed to just be friends. While the relationship has never been confirmed, the pair poked fun at the speculation during an interview with W. “We’ve been married 28 [years],” Zellweger joked of their bond.
Another one of George Clooney’s flings was with Sarah Larson. The duo met when Larson was working as a cocktail waitress in 2007 at a bar called The Whiskey. According to reports, Larson caught Clooney’s eye and he asked her to join him on a trip to Italy. The couple went on to have a whirlwind romance and Clooney brought Larson as his date to the Academy Awards in 2008, but they broke up in May of that year. Larson reportedly broke her foot when riding on a motorcycle with Clooney while they were dating.
Following his relationship with Larson, Clooney moved on with Italian actress Elisabetta Canalis in 2009. Canalis was first spotted on the back of George’s motorcycle in June 2009, but the couple didn’t make their first official joint appearance together until later that year in September. Clooney and Canalis called it quits in June 2011 after two years together. “We are not together anymore,” the duo told Us Weekly in a joint statement at the time. “It’s very difficult and very personal and we hope everyone can respect our privacy.”
Clooney wasted no time following his split from Elisabetta Canalis and went on to date former WWE champ Stacy Keibler in 2011. The couple was first linked in July 2011 when they were spotted vacationing in Lake Como. The duo went on to attend many red carpet events together, including the 2013 Academy Awards, but split that same June in 2013. “She knew he wasn’t looking to get married,” a source exclusively told Us Weekly at the time. Keibler went on to marry technology businessman Jared Pobre.
George Clooney and Croatian model Monika Jakisic were first linked through a brief fling in 2004, but later rekindled in 2007 when she was spotted with George on his yacht in St. Tropez. The couple eventually attempted to pursue a relationship in September 2013 after years of being on-and-off. “She’s not his official ‘girlfriend’ yet, but they’ve become very close. She has been seeing George almost every night,” an insider told Us of the couple in October 2013.
Despite his status as what many thought was an eternal bachelor, George Clooney made the decision to settle down when he met Amal Alamuddin in July 2013. The couple met after George’s friend brought Amal to dinner one evening. Shortly after this, the couple began dating in October and were engaged in April 2014. “This is the healthiest relationship I’ve ever seen George in,” a source told Us at the time. “He seems incredibly happy, and Amal is such a sweet and intelligent girl.” The couple officially tied the knot in September 2014 and welcomed twins, Alexander and Ella, in June 2017.