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As of 2014, Moore has been seen frolicking in Mexico in the company of 27-year-old Sean Friday.

2 Age: 55 Since splitting from Guy Richie, Madonna has been involved with a string of younger men! First there was Jesus Luz who was 23 at the time; then there was 24-year-old Brahim Zaibat; and, right now, she is currently dating 26-year-old Timor Steffens.

Her latest beau is model Kevin Sampaio, who at 31 is 27 years younger than the singer.

Sampaio was in her music video for “Bitch I’m Madonna” where they shared a kiss.

Leave it to Madonna to grab the crown — her relationship with 25-year-old Brahim Zaibat while she was 55 ties Sharon Stone's 30-year age gap.Women who date younger men are usually dubbed “cougars” while their male counterparts get away with it.And while there’s still a negative connotation attached to the term, women in Hollywood have long been unafraid to break convention.The star's largest dating age difference was a 16-year gap between her and ex-boyfriend Ryan Gosling. The consummate cougar, Jennifer Lopez, 46, is regularly snapped out with on-again, off-again beau Casper Smart who, at 28, was in grade school when her debut album On the 6 came out.