The East Wing
Our most popular and versatile private-party space features a custom-made mahogany bar, a line of Tiffany-inspired lights, comfortable maple wood chairs, copper topped high bistro tables and golden-lit sconces. Only open for private functions, The East Wing hosts gatherings for as many as 200 people or as few as 20. With a street-level entrance, full audio/visual capabilities and the best staff in the industry, we can promise that your first party at The East Wing won't be your last.
The Oak Cellar
If you venture downstairs in Jake's Dilemma, you won't believe your eyes. 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. Sidle up to the bar and order yourself a hearty draft or a colorful cocktail. With full audio/visual capabilities, i.e. TV's and great music, this room can host a wide range of events from Office Holiday Parties to Super Bowl Parties, from Birthday Parties to Bachelor Parties. And your friends (up to 100 of them) will be impressed that you found the newest and coolest private-party room on the Upper Westside.
The Living Room
Ready to kick back and enjoy a few drinks with friends? What better place than the Living Room at Jake's Dilemma, where you can relax on a comfortable couch and enjoy your cocktail while you catch up on all the gossip? Feel free to slip out of your private room and play a quick round of pool or throw some darts. A dedicated cocktail waitress will bring you one of our fourteen beers on tap, and our hot food buffet will keep you smiling all night. The room, which can hold up to 75 people, is perfect for all types of events, from Bachelor Parties to Birthday Parties, from Office Holiday Parties to Good Old-Fashioned Throw Down Bashes. Have a little fun, you deserve it.
Knock on the wrought iron speakeasy window and you may be ushered into the Speakeasy Room, a slice of old New York and the Upper Westside's premier private-party space. As the bartender pours you a strong drink and sets it on the long, dark bar, candlelight plays along the exposed brick walls and vaulted ceilings. Accommodating from 20 to 125 people, offering a full catering menu, audio/visual capabilities with a PA system for bands, a built-in stage, an alcove of cabaret tables around a gas fireplace, The Speakeasy Room hosts any type of party with the style and grace that built Manhattan (and the good cheer that ended prohibition!).
The Vice Room
Walk through a herringbone wooden passageway and host your event in the Vice Room. With an embossed tin ceiling, exposed brick walls, and Tiffany-style lighting about the private bar, The Vice Room is the perfect space to relax and enjoy your guests. If the mood strikes, pop in a DVD or request your favorite program on any of the five plasma TVs. Mingle with your friends and indulge all your vices.