Sean Penn and Robin Wright Reunite in New York City

Elizabeth Durand Streisand
Sean Penn and Robin Wright were spotted together at a New York City apartment. (Photo: Elder Ordonez/Splash News)

Time heals all wounds. Exhibit A: Sean Penn and Robin Wright, two of Hollywood’s most famous exes who have said some pretty nasty things about each other over the years and seem to have reconciled … again. On May 30, the stars were spotted together entering an apartment building in New York City. While Wright unlocked the door, Penn carried two large duffel bags. Both former loves dressed casually for the occasion, wearing sneakers and sporty jackets.

As a refresh of their, um, patchy history, Wright filed for divorce in December 2007, after 11 years of marriage. Apparently there was a change of heart, though, and the couple withdrew the paperwork just four months later. Things held steady for bout a year, until Penn requested a legal separation in April 2009. They reconciled shortly thereafter — but it only stuck until that August, when Wright filed for divorce for a second time, citing irreconcilable differences. In August 2010, they actually, really, finally divorced.

However, that seemed to be just the beginning of the bad feelings between them. During a 2012 interview, Penn explained, “When you get divorced, all the truths that come out, you sit there and go, ‘What the f*** was I doing? What was I doing believing that this person was invested in this way?’ Which is a fantastically strong humiliation in the best sense.” He went on to reason, “It can make somebody very bitter and very hard and closed off, but I find it does the opposite to me.”

Robin Wright Penn and Sean Penn attended the Academy Awards together on Feb. 22, 2009. (Photo: Steve Granitz/WireImage)

Penn added that he didn’t feel any shame in saying that we all “want to be loved by someone” and didn’t mince words about his past relationships. “As I look back over my life in romance, I don’t feel I’ve ever had that. I have been the only one that was unaware of the fraud in a few of these circumstances blindly.” OK, so he was also married to Madonna for a while, but since he didn’t specify if he was talking about one or both of his ex-wives, it’s highly possible he was taking a pretty serious jab at Wright there.

For her part, Wright has said that she and Penn fought for their marriage in large part for their two kids. “Divorce in and of itself, and with children, is devastating. Worse than that. One of the reasons why we got back together and broke up so much was trying to keep the family together. If you’ve got kids, it’s a family, and you try again, and you try again,” she told the Telegraph in 2014. “We did that for a long time.”

She also revealed that one thing that drew her to her next romantic interest, Ben Foster, was that he’d actually bothered to ask her on a date. Seriously. “I’d never, ever been asked out on a date before. Never. I was frickin’ married my whole life, and even before that I hadn’t been asked out,” she lamented. In other words, Penn wasn’t exactly the wining-and-dining type.

Since those interviews were given, Penn has dated Charlize Theron, and Wright was engaged to Foster. Both of those relationships fizzled out in 2015, though. Foster is now engaged to Laura Prepon, and the two are expecting their first child together. (So it’s safe to say Wright probably won’t be reconciling with him.)

While it seems most likely that Penn and Wright are in NYC for child-related activities (their 23-year-old son, Hopper, lives in the city and recently finished a stint in rehab), it’s almost impossible not to speculate about these two getting back together for the nine-thousandth time.


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