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Despite having been married twice, the public—and Penn himself, it seems—thought Charlize Theron was the real thing.

Not only did he publicly refer to her as the love of his life, but the pair were reportedly on track to tie the knot until Theron reportedly broke things off in June 2015.

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One odd bit of barely even circumstantial evidence that people are using to support the notion that the two, who were married for four years in the 1980s, are back together is that Madonna’s son Rocco Ritchie has been spending a lot more time in London with his father, director Guy Ritchie, of late, supposedly because he does not like Penn.

and Page Six are floating the rumor that ex-spouses Madonna and Sean Penn are an item again, citing a recent event wherein Madonna said some loving words about the Oscar-winning actor (“I want to say, Sean, I love you, from the moment that I laid eyes on you”) and the two were seen with “their arms around each others’ shoulders.”Page Six quotes some know-it-all as saying, “Everyone knows that Sean Penn is back with Madonna,” so I guess if this is the first you’re hearing of it, you’re no one.

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From his stunning ex-wife Robin Wright to bombshells like Scarlett Johansson, the Oscar-winning actor seemingly can’t be without a beautiful woman at all times.

And Sean was great with all of that." Theron, 40, said when she expressed interest in wanting to adopt at least one more child, she'd hoped her relationship with Penn, 55, would "go somewhere" before that happened.

That next-level relationship, she said, "ultimately did not happen," and they parted ways, reportedly after vacationing together last May.

The spy was returning from the bathroom, and told the mag: "I had to go through some curtains — and that's when I interrupted Sean and Natalie! "When they saw me, they were startled and quickly composed themselves." Despite having called her the love of his life, Penn and Charlize Theron broke off their engagement in June 2015.

The pair got together in December 2013, and sources say Theron, 39, was the one to break things off.

157 comments

  1. Two weeks after splitting with Charlize Theron, Sean Penn was seen with Minka Kelly. Here's a look at the MANY women the actor's dated.

  2. Mar 27, 2018. Sean Penn and Robin Wright were one of Hollywood's most celebrated couples for several years, dating all the way back to the mid 90's.

  3. May 6, 2017. be creativo Subscribe today and give the gift of knowledge to yourself or a friend Sean Penn Dating History 1 Sean Penn Dating History 2.

  4. The complete dating history of Sean Penn chronicling all of his alleged girlfriends and hookups over the years.

  5. Sean Penn is dating Charlize Theron; Sean Penn dated Petra Nemcova; Sean Penn dated Scarlett Johansson; Sean Penn was rumored to be with Valeria.

  6. Apr 5, 2018. Get all your Sean Penn news and gossip here. New Couple Alert — Charlize Theron Appears To Be Dating Halle Berry's Baby Daddy.

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