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14 New Yorkers' "How Old Do I Look" ages from spot on to so, so far off

Will Gleason

It's a number that most people don't exactly like to broadcast, but the new Microsoft web app How Old Do I Look can guess a person's age in mere seconds (along with their gender) from just a photo. We were curious how well the app would do with some notable New York faces, and it turns out: pretty well! With some very, very large exceptions. (Does anyone have the number for Donald Trump's dermatologist?)

David Letterman: Actual Age 68

Jimmy Fallon: Actual Age 40

Alec Baldwin: Actual Age 57

Mayor Bloomberg: Actual Age 73

Anderson Cooper: Actual Age 47

Anna Wintour: Actual Age 65

Sarah Jessica Parker: Actual Age 50 

Brooklyn transplant Hillary Clinton: Actual Age 67


Jay-Z: Actual Age 45

Andy Cohen: Actual Age 46

Donald Trump: Actual Age 68

Barbara Walters: Actual Age 85

Mayor De Blasio: Actual Age 53

Lena Dunham: Actual Age 28


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