George Clooney, a man many women drool over, is off the market for the first time in years.

Clooney, 52, is engaged to Amal Alamuddin, 36, after dating a little less than a year. According to USA Today, Alamuddin and Clooney have been spotted in London, New York, Tanzania and Seychelles together.

When the couple met Cindy Crawford and Randy Gerber in Malibu on Thursday, it was hard not to notice the giant rock on her hand.

Clooney has been married before. In 1989 he married actress Talia Balsam, though it ended in three short years, right before Clooney was cast in the hit show ER.

Since the break up with Balsam, Clooney has been a confirmed bachelor and no one could understand why! A great looking guy, talented actor, who wouldn’t want him?

It’s been 20 years since the last time Clooney was hitched, but he has had plenty of flings in between. Here’s a top ten list of George Clooney’s girlfriends leading up to marriage number two.

[new page = Stacy Keibler]
Stacy Keibler
The most recent Clooney girl was Stacy Keibler, a former wrestler and Dancing with the Stars contestant. They broke up after dating for two years in 2013. She now has a new lifestyle show Supermarket Superstar showing on Lifetime.

[new page = Kelly Preston]
Kelly Preston
Kelly Preston and George Clooney became a couple while they were both starting out in the acting industry. He moved in with her in 1988. Preston later dated Charlie Sheen before she married John Travolta in 1991.

[new page = Talia Balsam]
Talia Balsam
Talia Balsam captured George a year after being with Kelly Preston. Balsam and Clooney got hitched in Vegas in 1989 and were divorced three years later. Balsam is now married to John Slattery.

[new page = Kimberly Russell]
Kimberly Russell
Shortly after his divorce with Balsam, Clooney met a young Kimberley Russell on the set of a martini commercial and was in a relationship with her for three years before moving on. Russell has been seen recently in the movie Precious.

[new page = Celine Balitran]
Celine Balitran
Celine Balitran met Clooney in Paris while he was filming the movie The Peacemaker. The couple dated from 1996 to 1999. Balitran continued to model after the break up and was married for two years to David Rosenthal.

[new page = Krista Allen]
Krista Allen
George Clooney and Krista Allen met on the set of Confessions of a Dangerous Mind and were together from 2002 until 2006 with a brief break up in 2004. In 2010, Allen married Mams Taylor, but they divorced shortly after. She now runs a blog called Veggie Boom Boom.

[new page = Lisa Snowden]
Lisa Snowden
During the same time Clooney dated Krista Allen, he was also dating Lisa Snowden on and off before they also ended their relationship in 2006. Snowden is now a DJ for Capital Radio in London.

[new page = Renee Zellweger]
Renee Zellweger
Though they have only confessed to being great friends, Renee Zellweger and George Clooney have been rumored to have been a couple from 2001 until 2007. They were even spotted in 2006 sharing a New Year’s kiss. In 2007, the two denied any relationship and said they were just friends.

[new page = Sarah Larson]
Sarah Larson
Clooney got a lot of attention for dating Sarah Larson, a cocktail waitress from Las Vegas. They were together for less than a year and called the fling off in 2008.

[new page = Elisabetta Canalis]
Elisabetta Canalis
Elisabetta Canalis was the next girl spotted with Clooney, on the back of his motorcycle in 2009. The couple stayed together for two years before breaking up in 2011. Canalis continued to model and perform and has since been seen on Dancing with the Stars.