Maxwell Caldwell|Sean Penn is 'thrilled' to be single following 3 failed marriages: 'I'm just free'

2025-05-04 17:41:41source:LibertyCoincategory:Finance

Sean Penn is Maxwell Caldwell"thrilled every day" that he's a single man.

The 63-year-old actor opened up about his "trauma" following three marriages in an interview with The New York Times published Saturday.

"I'm just free," he said of his current status. "If I'm going to be in a relationship, I'm still going to be free, or I'm not going to be in it, and I'm not going to be hurting. I don't sense I'll have my heart broken by romance again."

Penn was married to Madonna from 1985 to 1989. His longest marriage to Robin Wright lasted from 1996 to 2010 and they had two children: daughter Dylan, 33, and son Hopper, 30.

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Most recently, he wed Australian actress Leila George in 2020. The couple officially separated in September 2021 and George filed for divorce in October. Their divorce was finalized in April 2022.

Penn told the Times that in past relationships "the first thing I see in the morning are eyes wondering what I'm going to do to make them happy that day. Rarely reciprocated."

The "Flag Day" star added that he loathed "The Real Housewives of Beverly Hills" and "Love Island" because it was the "background noise" in one of his marriages. "I felt my heart, my brain shrinking. It was an assault," he said.

His most successful post-breakup split has been with Madonna, Penn shared. "She's someone I love," he said, noting that they've worked together on raising funds for Haiti and she's helping him with a "really terrific" video for a peace summit about Ukraine.

"It turns out it's a lot quicker to repair a friendship after divorce if there are not kids involved," he said.

Penn added: "It took Robin and I quite a while. There was a lot of drama. Much more important to repair it if there are kids involved, but no easy swing, right?"

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