Sean Penn may have moved on from his marriage to Robin Wright years ago — but according to a source, the Hollywood heavyweight never fully got over the woman he once called his wife.
As Penn prepares to celebrate his 66th birthday on August 17, his complicated history with Wright is once again drawing attention, including claims that the Oscar winner tried to rekindle their romance long after their divorce was finalized.
Penn and Wright first began dating in the late 1980s and went on to become one of Hollywood’s most recognizable couples. They welcomed two children together, daughter Dylan Frances, now 35, and son Hopper Jack, 33, before tying the knot in 1996.
But their marriage was anything but smooth.
Wright filed for divorce in 2007, though the couple went through several attempts at reconciliation before finally ending their marriage for good in 2010.
Years later, Wright admitted their repeated breakups and reunions were largely driven by their desire to keep their family intact.
“Divorce in and of itself, and with children, is devastating,” Wright told The Telegraph in 2014.
She explained that the couple repeatedly tried to make things work because of their children, saying they would get back together, break up and then try again in hopes of preserving the family.
But according to a source, Penn wasn’t necessarily ready to close the door on their relationship even years later.
After Wright filed for divorce from her third husband, Saint Laurent executive Clément Giraudet, Penn allegedly saw an opportunity to grow close to his ex again.
“They’ve been hanging out a lot lately and, some friends say with a wink, enjoying occasional booty calls,” a source claimed in 2023.
Still, the insider said Wright had little interest in turning their renewed closeness into another full-blown romance.
“Robin’s more interested in co-parenting amicably and nothing much more,” the source claimed, adding that the situation was reportedly disappointing for Penn.
The source went even further, claiming Wright has remained the woman Penn has never truly been able to forget.
“Everyone will tell you he lurches from one bad romance to another because he’s still got Robin on his mind 24/7,” the insider alleged. “She’s absolutely the love of his life, no question.”
Wright, however, has publicly described their relationship in much less romantic terms.
Speaking to People in February 2023, the Forrest Gump actress said she and Penn had managed to rebuild a friendship after a period of estrangement.
“To be friends with the father of your children… I mean, it’s a gift, because we know divorce with children is one of the most difficult things in life,” she said.
Wright explained that no matter what happened between them romantically, she and Penn would always be connected because of their children.
“We’re always gonna be family, whether we’re together or apart, you know?” she said. “And I think that’s beautiful, and I wish that for everybody.”
Despite reaching a more peaceful place with Penn, Wright has also spoken candidly about the mistakes she believes they made while raising Dylan and Hopper.
Last year, the actress revealed she carries a “huge regret” over the way she parented their children, particularly when Penn was frequently away.
“He was gone so much of the time,” Wright explained. “He’d come back and be the policeman, and then he’d leave me with the residue.”
Wright said Penn tended to be the strict parent, while she would soften the rules after he left — creating two dramatically different parenting styles.
“We were both extremes,” she admitted. “They didn’t get that grey area in the middle, which is stern, and that is what they needed.”
Looking back, Wright said she wishes she had been tougher.
“I have a huge regret as a mother and have experienced the fallout of this regret for many years with my kids,” she said. “I wasn’t hard enough on them.”
More than 15 years after Penn and Wright officially ended their marriage, their relationship appears to have evolved into something calmer — a friendship built around their children and decades of shared history.
But if the source’s claims are accurate, Penn may have once hoped their renewed bond would become something much more.
