The Saddest Places To Drink In New York City This Valentine's Day

Will you be flying solo yet again this Valentine's Day? You're not alone. There are tons of single New Yorkers who are "focusing on their careers right now" and will be crowding karaoke spots, sports bars, and strip clubs in hopes of getting blind drunk with their best single friends. If you prefer bitter loneliness to good company, February fourteenth is a great time to do laundry, hit the hardware store, or make that IKEA run you've been putting off for so long. There are plenty of ways to power through the pain of being single on yet another Valentine's Day.

If you like the pain and sadness, if your idea of true romance is an empty liquor bottle split between you and your crushed ego, there are other places you can go. Sure, reserving a table for one at a romantic spot is sad, but you can do better than that. There are some truly soul-crushing spots in New York City that will make you believe not only that you won't likely love again, but that love is impossible in this cruel world. If you are looking to dive head-first into the dregs of sadness, you've come to the right place.

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Address: The Hudson River

Normally, the Staten Island Ferry is the best place to drink in all of New York City. Two Budweiser tall boys for $7? Where am I, Wisconsin? On a clear day, the Ferry provides a free and clear view of the Statue of Liberty without lines, fees, and the other trappings and tourist bullshit.

On Valentine's Day, however, the Ferry is a merchant of sadness (and booze, of course). If you ride during rush hour, you'll catch nurses, construction workers and policemen anxious to get home to the love of their life. If you jump on mid-evening, it will just be you, the crew, and the beer guy. If you take a cruise later at night you'll share the ride from the City with young couples returning from a pricey, boozy romantic dinner. A Valentine's Day ride on the Ferry will mean either an hour all by yourself downing cheap booze in a hazy fog, or sixty minutes drinking tall boys and eating popcorn surrounded by desperate, overpowering love with no possible escape except the chilly depths of the Hudson.

Address: 848 Washington St.

There are a number of options for drinking at the Standard Hotel this Valentine's Day. Don't worry which you choose, they will all serve to make you feel just as terrible about being poor as you already do about being single. Whether you are slurping down $25 whiskey sours at La Bain or you're chugging overpriced brews at the faux-rustic beer garden, you will be surrounded by people with few responsibilities and tons of money. The best part is that each and every one of them will have someone and you're all alone.

The Meatpacking District is New York's playground for the wealthy who don't feel like slumming it. Sure, one night in Williamsburg or the Lower East Side is fine, but eventually you just want to hang out with models, Grand Prix Drivers, and Diplo. Yes, your fellow patrons will remind you that while money can't buy happiness, it can buy a lot of other awesome things that you'll never in a million years get to touch.

Drinking in the Meatpacking District is like staring into an aquarium of opulence. You may graze the hem of some scantily clad party girl's garments while she nurses a cosmo and prepares to bed a man with a fine-tuned five o'clock shadow wearing a crisp tailored shirt, but you know you'll never actually swim in those forbidden waters. Hey, at least you can pretend you're the guy with the tailored suit and the five o'clock shadow as you dream your way to sleep in your cramped studio apartment.

Address: 143 E. 60th Street (at Lexington)

You probably don't know about the Subway Inn. This is a spot where the bellhops and clerks of the high-end retail district come to drown their sorrows after pulling their fifth double-shift in a row. Across the street from Bloomingdale's, a few blocks from the Apple Store, and within spitting distance of Chanel, Bergdorf and all the rest, this dive stands in defiance of the privilege choking it from all sides. If you want to hear war stories about nannied toddlers puking all over a clerk's shoes or employees fired for saying the wrong thing to a fur coat wearing debutante, this is where you should go. Their vitriol should be especially potent on Valentine's Day, when shifts end just late enough to ensure that these workers will get home just in time to see their spouse fall asleep.

Address: 120 Cedar St.

There are few bars that actually look inviting in the cold gray monotony of the Financial District. O'Hara's is one exception. This is your old-fashioned, standard New York Irish-style pub...that happens to be located half a block from the 9/11 Memorial. O'Hara's is a lively, exuberant joint when it's crowded, but if it's empty, you feel the ghosts. FDNY and NYPD badges line the mirrors and shelves in the bar that is now as much a memorial as it is a tavern. Stepping into O'Hara's is quite the experience, but probably one best saved for a day other than February 14.

Address: 34th St. between 7th and 8th Ave.

To the uninitiated, it probably seems that all transit station bars are created equally terrible. Oh, you have so much to learn. What makes the T.G.I.Fridays next to the Amtrak terminal so pathetic? Let's start with the arrivals and departures chart in the photo. This is the view from this particular T.GI.Fridays. If you drink here, you'll share bar top elbow room with beleaguered businessmen drowning their sorrows as they watch their delayed train's number sit, immobile at the bottom of the chart as scores of other trains leave the station ahead of theirs.

The kind of person who regularly rides Amtrak is perpetually disappointed. Yes, the Megabus and the Greyhound attract the dregs of society, the ex-convicts and the graduate students. But, Amtrak riders are a pack of "almosts." They were almost going to make their boy's soccer game, but the presentation ran long. They were almost going to nab that promotion, but they hired that hotshot Ivy grad. They were almost going to make it home in time for that romantic Valentine's Day dinner, but that Keystone Corridor line is delayed. If you do find yourself in this particular T.G.I.Fridays on Valentine's Day, buy the guy wearing the monochromatic shirt and tie combo from Kohl's a $7 Budweiser. He needs it. You'd better be quick about it though, his train is almost at the platform.

Address: 500 E. 9th St.

Mayors Bloomberg and Giuliani did a great job of making the homeless seem invisible. Any reports you read about New York prior to their administrations tell tales of sleeping bags and cardboard spread across on sidewalks up and down the island. These days, you'll pass a down-and-out man pushing a shopping cart through Central Park or a couple wrapped in a filthy blanket in your building's lobby, but generally the homeless are kept out of the public eye. Tompkins Square Park is one public area in Manhattan where you less fortunate still congregate. Yes, you can see the remnants of Occupy Wall Street and dog-loving gutter punks pretending to be homeless in Union Square, but if you want to spend Valentine's Day with the genuine article, head over to Tompkins Square. Just be sure to put a brown bag around your bottle of Mad Dog or you might get rousted.

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.