Address: Anywhere in Times Square
Admit it, when you clicked on this article you expected to see Times Square check in at the top of the list. Just because it's predictable doesn't make it untrue. Anyone who has spent more time in New York than it takes to shop at Macy's, grab a bite at the Olive Garden, and catch a matinee of Wicked knows that Times Square is to be avoided at all costs. Of course, no matter how carefully you try to sidestep the area, at least twice a year you find yourself staring at a neon billboard of an American Eagle ad featuring an under-aged girl in a plaid bikini top and Daisy Dukes jumping off of some backwoods pier. Meanwhile a guy wearing a sandwich board tries to convince you to shop at the M&M Store.
Drinking in Times Square on Valentine's Day is just begging to dredge up your emotional baggage. Middle-aged couples from middle America—you know, like the parents who stand by you even though you wrote "Freelance Dog Walker" on your tax forms—with fanny packs and outdated cameras, dine on Guy Fieri's chicken wings as they enjoy a weekend away from the kids. Then there's the young newlyweds, dressed in equal parts Aeropostale and Abercrombie, waiting in line for a romantic meal at Bubba Gump. An endless supply of these couples mills about Times Square on V-Day and they all have one thing in common: delirious happiness, a happiness that will make you miserable. There is no novelty beer large enough, no t-shirt kitschy enough, no crazy straw crazy enough, to distract you from this vision of the life you could have had. Every couple is a bizarro version of the life you would have led if you moved down the block instead of across the country when you finished school. Hanging out in Times Square on Valentine's Day is like watching your own personal version of It's A Wonderful Life, except you know you're never going back to Bedford Falls, because people are lame there and there are no vegan options.