George Clooney's 7 Longest Relationships

They say, "once bitten, twice shy," and this seemed like it would always be the case for superstar George Clooney, who vowed to never remarry after his 1993 divorce from actress Talia Balsam. Clooney became a perpetual bachelor, often in the news with a new beauty on his arm.

However, it seems things have changed. News broke on Saturday, April 26, that George popped the question again, asking his 30-something girlfriend Amal Alamuddin to marry him. The couple has only been dating since October of last year, and things seem to be moving pretty fast for the lovely duo. But what about the 50-something Oscar winner's past relationships, some of which lasted quite a while without taking that next step toward engagement?

Here's a look back at Clooney's longest relationships.

Rumors began to swirl about Clooney and Keibler when she was seen vacationing at his home in Lake Como, Italy. Keibler is a former WWE professional wrestler and, like Elisabetta Canalis, was a contestant on Dancing With The Stars. Clooney and Keibler called it quits in July of 2013. Soon after, Keibler began dating Future Ads CEO Jared Pobre, and they were married in March 2014. Keibler also announced that she was pregnant with the couple's first child. She dated Clooney for around two years. 

Italian actress and model Elisabetta Canalis, a former contestant on Dancing With The Stars, was first linked to Clooney when she was seen riding on the back of his motorcycle. The couple decided to go public with their relationship by appearing together on the red carpet at the Venice Film Festival. Speculation that George had asked Elisabetta to marry him exploded when she was seen with what looked like an engagement ring, but reps denied the reports. In June of 2011, George and Elisabetta released a joint statement confirming their separation. They dated for about 18 months. 

Snowdon is an English actress and television host who met Clooney when the two shot an advertisement for the Italian vermouth Martini. Their relationship was tabloid fodder for years in America and in England, but work got in the way of their love, and the couple officially called it quits in late 2005. Since their relationship, Snowdon has said that she's had a hard time finding men, because men think they can't live up to her Oscar-winning ex.

So who is your favorite of all of Clooney's exes?

George met Krista in 2002 while directing Confessions Of A Dangerous Mind, in which she had a small role as "pretty woman." However, their relationship only lasted two years. Allen still acted and modeled after the split, and eventually married British musician Mams Taylor in 2010, but they divorced in 2012.

Like the actor's current fiance, Celine Balitran was one of the few women he dated that wasn't an actress. Celine was a 23-year-old Parisian waitress that George met while filming the action thriller The Peacemaker in Paris, France. Celine ended up following George back home to Los Angeles, and living with him until they broke up in 1999.

Clooney and Preston began dating in 1987, shortly after the actress finalized her divorce from actor Kevin Gage, and the two moved in together in 1988. The relationship lasted two years. Preston went on to marry John Travolta in 1991 and the two are still married to this day. 

Balsam was the first and only woman Clooney has married. They got married in Las Vegas in 1989, and then divorced in 1993. Clooney has since admitted that it was a mistake to get married at that point in his life and he feels that he didn't give Balsam a "fair shot." Balsam went on to marry Mad Men actor John Slattery in 1989, and she even plays Slattery's first wife Mona Sterling on the AMC show.