But his last serious girlfriend, Sports Illustrated and Victoria's Secret model Jessica White certainly approves.
'I think Sean needs a good woman in his life,' Jessica revealed in a new interview.
Sean, 50, and 26-year-old Jessica dated off and on in 2009 and 2010 after he split from his wife of 14 years, Robin Wright Penn.
'They're great together,' Jessica tells entertainment website Popeater.com.
'Sean is a really lovely man,' Jessica added saying she admires the actors humanitarian work in Haiti.
'That's where he finds his peace and his refuge. I think that's a great job. That's his calling. He's very passionate.'
Twice-married Penn and Scarlett, 26, were linked together back in January, just weeks after Scarlett announced her divorce from her husband of two years, actor Ryan Reynolds.
They have been snapped together a couple of times, including last weekend at Reese Witherspoon's wedding.
The are said to have met at the Chateau Marmont in West Hollywood while Scarlett was filming We Bought A Zoo, her new movie alongside Matt Damon.
But Scarlett's representative has denied any romance saying the pair have been 'friends for years.'
Sean has been married twice, the first time to superstar singer Madonna.
Do you guys approve of your ex's new significant other(s)?