Jake’s Dilemma

With 14 beers on tap and 50 different kind of bottled beer to choose from, you’ll know exactly what Jake’s Dilemma is: A shot and beer bar that brings a hardcore, downtown vibe to the Upper West Side, Jake’s Dilemma sports a Foosball, Buck Hunter Pro video game, an outdoor cafe, and rock and roll all night long.  Jake’s Dilemma does not have a kitchen, but if you’re like us, beer is food, and Jake’s serves a hearty meal. Food is available from sister bar The Gin Mill [see menu]

Jake’s Dilemma opened its doors in September of 1994, and the Upper West Side has never been the same. Now regarded as the landmark bar of the Upper West Side, Jake’s Dilemma is in its second decade of being the place to be.

Jake's Dilemma interior

Daily Specials:

Happy Hour:
Monday – Thursday: 4pm – 8pm
Friday: 3pm – 8pm
Saturday – Sunday: 12pm – 8pm
Whole bar 1/2 price

$3 Drafts & Shots

$2 Domestic Mugs
$10 Domestic Pitchers
$4 Shots

1/2 Price Beer (Bottles, Drafts and Pitchers)
$3 SoCo Lime & Flavored Vodka

$4 You Call It:  Drafts, Bottles, Well Drinks, & Shots

Bucket Night
$14 domestic buckets of beer (5)
$4 “J” Shots: Jack, Jager, Jameson

1/2 Price Bar 3pm-8pm

Power Hour 8pm-9pm
$1 domestic mugs, $2 well shots


Sports at Jake’s Dilemma
Jake’s Dilemma is the home of all New York sports. Catch all the local games as well as all out of market NFL Sunday Ticket and MLB Extra Innings games on DirecTV.
NFL Sunday Ticket
MLB Extra Innings
Mega March Madness

Softball teams from Central Park welcome.

Parties at Jake’s Dilemma:

The Oak Cellar:
  Under an arched stone wall, there is a hand-carved mahogany door that leads into a stylish medieval wine cellar, complete with original masonry mosaics, inlaid Spanish tile, stain-glass lights, a renaissance tapestry and cobblestone floor.
Suitable for private parties up to 80 people, with full audio/visual capabilities, this room can host a wide range of special events from office holiday parties to Super Bowl parties, from birthday parties to bachelor parties. [more info]

The Living Room. Open up the red velvet curtains and feel like a VIP as you look over the main bar crowd. The Living Room is fitted with burgundy leather couches that you can lounge on as a dedicated cocktail waitress brings you one of fourteen beers on tap or your favorite cocktail. You can also choose to add a hot food buffet from an extensive catering menu. The Living Room can hold up to 50 people, and is perfect for all types of events. [more info]
The Living Room: Private party room at Jake's Dilemma

If a private room is not for you, also inquire about their “Main Bar” parties that allow you to mix and mingle with other customers of Jake’s Dilemma.

Contact the party planners at Eat, Drink, and Be Merry 212.585.2371.

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