While you can never go wrong with a nice Bordeaux, everyone knows that the best thing to pair with your meal is a juicy dose of people-watching. In a city like New York, you're bound to spot an "influencer," a celeb, or just a few chic characters strutting by. We mean, who gets all dressed up for a moment out, only to be forced to look solely at their dining companion? Boring. Suggest a table at one of these hot spots with sidewalk seating, and the entertainment is free.

[Photo via @maddietsang]