A study by Match.com puts the yearly cost of dating at about $1,596, which averages out to a nice and affordable $30 date each week. Cut down on your afternoon iced caramel macchiato and you’re all set to get your dating groove going. But that’s pocket change compared to what singles are spending in large cities to go on dates. According to statistics released by Deutsche Bank, a cheap date in New York City will cost your wallet the criminal amount of almost $135 for the both of you.