Sean Penn & Leila George – 32 years
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It took a while for this one to go public, but it finally did this year. Penn and George have been spotted together causally since 2016, but finally walked a red carpet together in 2020. Good for them for staying out of the spotlight.
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George, who is actor Vincent D’Onofrio’s daughter, was just 26 years old when the couple first started dating. Penn was 56. George is working on an acting career of her own and with the men in her life, you’d think that will come to fruition.
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