10. Charlize Theron & Sean Penn
Sometimes a big age gap doesn’t work out, despite the duo seeming like a great pair. Sean Penn and Charlize Theron have a 15 year age gap between them, but were seen happily attending red carpet events arm in arm for over a year and a half. The two were even engaged.
They began dating in 2013, after their decades of friendship blossomed into romance, and at one point Penn filed to adopt Charlize’s son. Following their break-up, a source close to Theron said, “Charlize was seeing that it was just too intense for her and she needed a breather. She still loves him and respects him to the fullest but she just needed to get out of his intense atmosphere.
She is still very young at heart and he plays things by the book.” The two have managed to keep the breakup amicable, and have remained on very good terms.
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