In 2009, Sean was spotted with the gorgeous and intelligent Natalie Portman, at the bar inside of the Sunset Tower Hotel. Apparently the two were trying to enjoy a quiet dinner, but they kept being bothered by all of the agents of the press, who were understandably excited about seeing them together.
However, Portman later told E! Online that the rumors about them being romantic were just that – rumors.
Back In The Day
But what was Sean Penn up to before he took the plunge with Madonna? Well, in his past, he was extremely dedicated to his relationship with the beautiful Elizabeth McGovern. When they were together, he really thought she would be the one walking down the aisle with him. The couple fell in love while working together on Racing with The Moon, and he very quickly got down on one knee.
Of course, she was so excited by the thought of being married to THE Sean Penn that she said yes. However, not long after she had a change of heart. She told him that she was “too young,” and she wasn’t ready to make that kind of commitment at that time. Later she would say that she was “lucky,” for making that decision.
Setting the Bar High
Just when it seemed as if Penn was only interested in actresses, he decided to shake things up a little bit and get involved with Australian model Elle Macpherson.
They were spotted canoodling at an Upper Eastside restaurant in NYC, in 1996. One onlooker described the pair as only having eyes for each other, and very physically affectionate towards one another.
Addressing the Gossip
Portman, who admitted that she typically doesn’t even acknowledge, much less respond to, rumors about her romantic life – had something to say about this whole thing. She flat out told reporters that the entire story about their being something between her and Sean was “fabricated.”
But the press just couldn’t let it go, and they kept trying to spin everything to make it seem as if the two were dating. One anonymous source in Hollywood jokingly said that Portman, at 27, was, “far too old,” for a star of Sean’s age (48.)
Sean & Robin
Actress Robin Wright, who is well known for her role as Claire Underwood on House of Cards, started dating Sean right after his split from Madonna. The two actually dated for a long time before he decided to pop the question – undoubtedly because rushing in to things didn’t work out so well for him the first time around.
Luckily, he and Wright ended up having a wonderful stint of marriage, during which they had two beautiful children.