21 Famous Women And Their Young Lovers

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3. Jennifer Aniston

While Jennifer Aniston is just two years older than her fiancé Justin Theroux, the gorgeous actress is no stranger to dating younger men.  She has been linked to several guys who are significantly younger than her, the youngest of them all being John Mayer, 9 years her junior.

They began their romance in 2008 after spending five hot days together in Miami, and after a brief split got back together, only to break up for good in 2009. Aniston learned the hard way that it was impossible to bridge the age gap between them, or even stay friends when Mayer revealed that he ended their relationship because he couldn’t change the fact that she was older than him.

Here’s what he infamously told Playboy:

“I’ll always be sorry that it didn’t last. In some ways I wish I could be with her. But I can’t change the fact that I need to be 32. The brunt of her success came before TMZ and Twitter. I think she’s still hoping it goes back to 1998. She saw my involvement in technology as courting distraction. And I always said, ‘These are the new rules.’”

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