Celebrities dating older men

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He was definitely piping those cakes down before Madonna turned into Skeletor and was moderately attractive.

Elizabeth Taylor – The late Liz had her fair share of men that had an open shot at those cakes. Let’s also not forget her…unique…relationship with Michael Jackson who, yes, was still technically Black.

So Madonna may have famously flamed out with former husband Guy Ritchie, but that’s not to say that things won’t work out with Zaibat.

At a mere 10 years younger, perhaps Ritchie was just too old for her.

Mariah Carey, 42, has had twins with Nick Cannon–that’s a 10-year age gap. But top of the tree, as ever, is Madonna, 53, who is at least considering a marriage proposal from her 24-year-old boyfriend, Brahim Zaibat.

Yet women shouldn’t assume that all younger men will eventually want children. Despite the prevalence of the cougar trend, older women shouldn’t expect society to treat their relationships with younger men as “normal.” They will likely field their share of raised eyebrows from friends and family members.

Says Winter, “More and more, I’m meeting young men partnered with women 15-20 years older, both of whom don’t want to have children.” In fact, the desire to remain child-free may account for many younger men seeking older female partners in the first place. So a woman’s ability to successfully date a younger man may ultimately come down to being an independent thinker who is brave enough to buck the system (kind of like Madonna).

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