George Clooney was formerly known as one of Hollywood's most eligible bachelors before his life of marriage and fatherhood.
He has dated one of the most popular women in Hollywood such as Renee Zellwegger, Kimberly Russell, Teri Hatcher, Dedee Pfeiffer, Denise Crosby and Kelly Preston.
However, one woman who had Clooney's heart was Real Housewives of New York City star Carole Radziwill.
Radziwill and Clooney dated in the late '90s while he was on the show that gave him his big break, ER. However, she recently ranked Clooney's performance in bed while playing a game of truth or dare with her Real Housewives of New York co-stars.
Radziwill was asked to rank the acclaimed actor on a scale of 1-10.
"He's definitely a nine," the 53-year-old reality star said. "It was a long time ago! we dated literally during the Eisenhower administration."
However, the former couple has moved on throughout the years. The Ocean's Eleven star married his wife, Amal, in December of 2014 and became a first-time dad to twins, Ella and Alexander, on June 6.
As for Radziwill, she has been dating vegan chef, Adam Kenworthy, since 2015.
However, despite how much time has passed, Radziwill continued to speak good things about her ex-boyfriend and his wife.
"[She] seems like an amazing woman," she said. "I think it's fantastic, and when anyone falls in love it's a good thing for everybody."