Stumble Inn: This cheap Upper East Side establishment has the best happy hour specials including Mondays 7pm - close $1 drafts. It's a bit "fratty" and has two beer pong tables set up at all times. If you are into sports, the TVs usually play whatever game is on. Not the most exciting atmopshere but you will likely leave tipsy, happy, and with most of your cash still in your wallet. It's stumbling distance from the subway on 76th St and 2nd Ave.
Brother Jimmy's BBQ: Although this is a local chain restaurant, if you find a Brother Jimmy's you've found young hardworking professionals and cheap beer. One must not pass up this opportunity to drink PBR from a can and relive the old college days in a casual "southern" style environment. Check their website for weekly specials.
Pig 'n' Whistle: I had to include at least one Irish Pub on here! Although I hate on Midtown (too crowded with tourists and a lack of foodie restaurants, stay away from Times Square if you want an authentic NYC experience), it is centrally located if you are meeting people from downtown, uptown, Queens and New Jersey. Pig 'n' Whistle has three locations, live music, and pretty decent food. This is my go-to if I am between 59th St and Grand Central Station on the East Side.
The Gingerman: With over 100 specialty beers to choose from and a rather large space to mingle in, The Gingerman is the place to go if you are in the Murry Hill neighborhood and with 50 of your closest friends.
Sidebar: Conveniently located one block from Union Square, Sidebar is on the corner of 15th St and Irving Place. It has large windows which they open during nice weather (I love the indoor outdoor space!). The food is delish: truffled bleu cheese french fries, chicken fingers and honey mustard, hummus plate - be still my heart! This is also my favorite College Football Game Day bar as it is one of the official Gator bars in the City (University of Florida Gator Alumni holla!). After drinks I highly suggest a stroll up Irving Place to Gramercy Park, its so charming and romantic!
Pete's Tavern: This Irish Pub is basically next door to Sidebar. Grab a Guiness, a burger, sit back and people watch. Sit outside to enjoy the architecture and passers-by. It also boasts being the oldest continuously operating bar in NYC.
Pravda: This is an upscale SOHO Russian Vodka bar. It's underground bunker speak-easy vibe creates a mysteriously sexy atmopshere. They serve only the best of the best and in the most exciting ways (and I'm not just talking about the ultra hip and sexy bartenders). Having a vodka martini here transports you and your comrades to the old country with a new flare.
The Blind Tiger: This hole-in-the-wall Greenwich Village bar has a well edited selection of local draught specials and a very casual atmopshere. The food is cheap and mighty tasty. You will be overdressed if you are wearing a collared shirt but that doesn't stop the afterwork crowd from enjoying themselves.
Tortilla Flats: LOVE this divey Mexican bar. It has one of the most festive atmospheres I've ever experienced. You will be drinking pitchers of Margaritas and eating your fill of chips, salsa, guacamole, and sloppy bar quality mole pollo, tacos, and burritos. If you go on your birthday, in addition to happy hour, there is a chance at free tequilla shots for your table. I'll let you find out how to get it. (Ernest Borgnine fans unite!)
The Rusty Knot: Although nestled on the West Side Highway (aka BFE), it's worth taking the trec out to this time capsle. Once you step inside you are transported to a 1970's nautical themed lounge. Drink Tecate in a can and relax in the glorious wood panneling, fish tanks, and pool table. And dispite appearances wearing a mustache is not required. (No website for this one; it's located in the West Village, 425 West St on the corner of W 11th St).
Frying Pan: This is the ultimate outdoor happy hour destination. The bar consists of a number of floating vessles out on the Hudson River. On a beautiful day you are standing elbot to elbot with beautiful people (yes, people do go here to be seen). If you get hungry it's worth waiting for a burger and fries. Yum-mie! Leave at dusk though as it gets sketchy after the sun goes down. (No website for this one either; its located at 63 Franklin D. Roosevelt East River Drive and E 24th St).
Boat Basin: This might be my only choice for the Upper West Side (sorry people, I just don't go up there). It's also a great outdoor destination and much more relaxing than Frying Pan. Food is good, drinks are good, and the views of the river are awesome.
Do you have any favorite NYC happy hour destinations?