Wednesday, April 22, 2026

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Sean Penn had to win back Leila George

Sean Penn and Leila George had broken up just a few months before they got married.

The ‘Milk’ actor wed the 28-year-old beauty in a low-key ceremony on 30 July and though they first dated in 2016, their relationship had been on/off until the last time they went their separate ways and the 59-year-old star realised he’d made a huge "mistake" and "worked hard" to get things back on track.

A source told People magazine: "Leila has been in Sean’s life for a while. They got together and then they broke up, and Sean won her back.

"He realised he had made a mistake and when he felt he might lose her, he worked hard to get her back."

The couple isolated together amid the coronavirus pandemic, which helped strengthen their relationship and made them realise their future together.

The insider added: "They got back together during COVID and became really close and got engaged a few months ago, early during quarantine."

Sean – who has children Dylan, 29, and Hopper, 26, with ex-wife Robin Wright – recently revealed he and Leila married over Zoom, with the officiant carrying out proceedings via video link.

He said: "We did a COVID wedding. By that, I mean it was a county commissioner on Zoom and we were at the house with my two children and her brother, and we did it that way."

Sean – who also formerly married to Madonna – has previously admitted he can be "difficult" in his personal life, but praised Leila for knowing him inside and out.

He said: "Am I difficult? Yeah I think so. I will say I’m a person who feels and expresses energetically, I’ve misled people into thinking it’s all about me.

"I think the interview you’re talking about would be a lady named Leila George, she knows me better than I do on this level, that doesn’t mean I agree with her perceptions but I certainly find them fascinating. … She’s the gal in my life."

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