Jake's Dilemma Introduce
In the vibrant heart of New York City's Upper West Side, Jake's Dilemma stands as a true neighborhood institution. This beloved bar and grill has been a staple of the Amsterdam Avenue scene since 1994, offering a quintessential New York pub experience with a lively, downtown atmosphere. It's a place that effortlessly blends the relaxed feel of an old-school pub with the high energy of a modern sports bar. Whether you're looking to watch a big game, challenge a friend to a round of beer pong, or simply enjoy a laid-back drink after work, Jake's Dilemma provides the perfect backdrop. The atmosphere is casual, cozy, and trendy, making it a popular spot for a diverse crowd, from local residents and college students to groups of friends and tourists exploring the city.
What sets Jake's Dilemma apart is its comprehensive approach to a good time. It's not just a place for drinks; it's an event venue in its own right, known for its bar games and private event spaces. The food and drink menu is designed to fuel the fun, with a great selection of classic pub fare and a wide variety of beverages. From delicious burgers and wings to a massive selection of drafts, bottles, and cocktails, there is something for every taste. The bar is a hot spot for sports enthusiasts, with numerous TVs broadcasting a variety of games. The friendly and fast service ensures that you can focus on the fun without any hassle. This combination of a welcoming atmosphere, great food and drink, and a multitude of entertainment options makes Jake's Dilemma an unforgettable destination on the Upper West Side.
Situated at 430 Amsterdam Ave, New York, NY 10024, Jake's Dilemma is at the heart of one of the city's most dynamic neighborhoods. Its location is easily accessible for anyone in the New York region. While public transportation is a popular choice for many, with several subway stations and bus stops nearby, the bar also offers the convenience of free street parking, which can be a valuable find in this bustling area. The bar's entrance is wheelchair accessible, as is its restroom, ensuring that it can accommodate a wide range of guests. The prime Upper West Side location makes it an ideal meeting spot for groups, whether for an impromptu night out or a planned gathering. For those who prefer to enjoy the city air, Jake's Dilemma also offers outdoor seating, a great way to take in the vibrant street scene while enjoying a drink or a meal.
Jake's Dilemma provides a range of services that go beyond a typical bar experience. They are designed to create a fun, engaging, and convenient environment for all patrons. The key services include:
- Dine-In Service: Enjoy a full menu of food and drinks with table service, perfect for a casual lunch, dinner, or a night out.
- Takeout: If you're on the go or prefer to eat at home, the bar offers a convenient takeout service for its food menu.
- Private Event Hosting: Jake's Dilemma is a highly recommended venue for private events, from graduation parties to corporate gatherings. They have dedicated private rooms, like the Oak Cellar and the Riverside Room, that can be reserved for groups.
- Bar Games: The bar is known for its variety of bar games, including multiple beer pong tables and the Upper West Side's only foosball table, making it a great place for friendly competition.
- Happy Hour: The pub offers fantastic happy hour specials on both drinks and food, making it a popular spot for an affordable and fun after-work gathering.
- Trivia Night: The bar hosts a lively trivia night, a great way to test your knowledge, socialize, and have a fun weeknight outing.
What makes Jake's Dilemma a true standout in the New York City bar scene? It's a combination of unique features and a lively atmosphere that sets it apart. Some of the most notable highlights include:
- Lively Sports Atmosphere: With a multitude of TVs broadcasting a wide range of sports, Jake's Dilemma is a top destination for sports fans who want to catch a game with a crowd.
- Great Beer and Cocktail Selection: The bar boasts an extensive selection of draft beers, bottled beers, and craft cocktails, ensuring that there is a perfect drink for everyone.
- Food and Drink Specials: The daily happy hour deals and specials on drinks and food are a major draw, providing great value for patrons.
- Entertainment: The bar is a hub of entertainment with its famous bar games, live DJs on weekends, and a dedicated dance floor, creating a dynamic and fun environment.
- Private Event Spaces: Jake's Dilemma offers well-appointed private rooms for events of various sizes, with dedicated staff and catering options.
- Casual and Friendly Vibe: The atmosphere is relaxed and welcoming, attracting a friendly crowd that makes it easy to socialize and have a good time.
For inquiries, reservations for private events, or to learn more about specials, you can contact Jake's Dilemma directly:
- Address: 430 Amsterdam Ave, New York, NY 10024
- Phone: (212) 580-0556
For a first-time visitor to Jake's Dilemma, navigating the menu can be a fun adventure. The bar and grill is known for its classic pub fare, and a few items are particularly worth choosing to get the full experience. The Wings are a perennial favorite, often praised for their satisfying flavor and perfect crispiness. Paired with a side of Smothered Fries or Tots, topped with cheese, bacon, and jalapenos, you have a perfect combination for a night of watching sports or playing games. For a more substantial meal, the Jake's Dilemma Burger is a signature choice, loaded with Swiss cheese, bacon, and jalapenos for a flavorful kick. The Philly Cheese Steak is also a popular and satisfying option.
When it comes to drinks, the extensive beer menu is a highlight. With a variety of drafts and over 35 bottled beers, you're bound to find a new favorite or a trusted classic. Be sure to check out their daily specials, which often feature great deals on drafts and cocktails. Speaking of cocktails, the bar offers a creative selection of signature drinks and classic libations, ensuring there's something to quench every thirst. Whether you're planning a full event in one of their private rooms or just dropping in for a quick bite and a beer, the combination of great food, an impressive drink menu, and a lively atmosphere makes Jake's Dilemma a top choice. The bar's reputation for being a fantastic place for groups and for hosting memorable events is well-deserved, so consider it for your next outing with friends or a special celebration.
Jake's Dilemma Food & drink
Burgers & Sandwiches
- Grilled Cheese $10.99
Fries, Tater Tots or Salad
- Grilled Chicken Wrap $15.99
Fries, Tater Tots or Salad
- Chicken Caesar Wrap $15.99
Fries, Tater Tots or Salad
- Fried Chicken Sandwich $15.99
Chipotle Apple Slaw, Pickles, Chipotle Aioli on a Brioche Bun Fries or Tots
- Grilled Chicken Sandwich - Regular or Buffalo Style) $15.99
Fries, Tater Tots or Salad
- Burger $15.99
Fries, Tater Tots or Salad
- Jake's Dilemma Burger $18.99
Topped with Swiss cheese, Bacon and Jalapenos. Choice of Fries, Tater Tots or Salad
- Philly Cheese Steak $15.99
Fries, Tater Tots or Salad
- Pulled Pork Sandwich $13.99
Slow cooked pulled pork w/BBQ sauce topped w/Chipotle Apple Slaw w/Fries or Tots
Apps
- Fries or Tater Tots $7.99
- Sweet Potato Fries $8.99
- Smothered Fries or Tots $10.99
With Bacon, Cheddar, Jalepeño, and Sour Cream
- Cheese Quesadilla $12.99
with peppers, onion and mushroom
- Mozzarella Sticks $8.99
- Mac n Cheese Wedges $7.99
- Jalapeno Poppers $7.99
- Hot Dog $3.99
- Chicken Fingers $13.99
BBQ, Ranch or Honey Mustard
- Wings $0.00
Mild/Med/Hot/BBQ/Honey BBQ/Jamaican Jerk with Ranch or Bleu Cheese
- Boneless Wings $13.99
Buffalo/BBQ/Thai Chili/Honey BBQ/Jamaican Jerk Ranch or Bleu Cheese
- Homemade Guacamole $11.99
With Fresh Tortilla Chips and Salsa
- Old Fashioned Sliders $13.99
American Cheese & Grilled Onions w/Fries or Tots
- Pulled Pork Sliders $13.99
Slow cooked pulled pork w/BBQ sauce topped w/Chipotle Apple Slaw w/Fries or Tots
- Nachos $13.99
- App Sampler $25.99
Wings, Mozz sticks, Fries, Quesadilla, and Mac n Cheese Wedges
- Caesar Salad $10.99
- House Salad $10.99
Mixed Greens, Cucumber, Cherry Tomatoes and Red Onion
Cocktails
- Ace Paloma $12.00
Maestro Dobel Diamante Tequila, Lime, Juice, Grapefruit Juice, Grapefruit Soda & Simple Syrup
- Negroni $12.00
Gin, Campari & Sweet Vermouth
- Aperol Sprtiz $12.00
Aperol, Prosecco, and Club Soda
Drafts
- Angry Orchard Cider $8.00
- Blue Moon $8.00
- Blue Point IPA $9.00
- Bud Light $7.00
- Coors Light $7.00
- Guinness $9.00
- Jake's Amber $8.00
- Kona Big Wave $9.00
- Modelo $8.00
- Sam Adams Seasonal $8.00
- Stella Artois $8.00
- Goose Hazy IPA $9.00
Premium Wine
- Placido Pinot Grigio $12.00
- Natura Sauvignon Blanc $12.00
- Bigfoot Rose $12.00
Bottles
- Becks $8.00
- Brooklyn Lager $8.00
- Bud $7.00
- Bud Light $7.00
- Coors Light $7.00
- Corona $8.00
- Corona Light $7.50
- Lagunitas IPA $8.00
- Sierra Nevada Pale Ale $8.00
- Stella Artois $8.00
House Wine
- Trebbiano (White) $10.00
- Sangiovese (Red) $10.00
Cans
- Austin Original Cider $8.00
- Austin Pineapple Cider $8.00
- Bud Light Seltzer $4.00
Assorted Flavors
- Cigar City Jai Alai IPA $8.00
- Founders All Day IPA $8.00
- High Noon $12.00
Assorted Flavors
- Michelob Ultra $5.00
- Miller Lite $4.00
- NUTRL $6.00
Assorted Flavors
- Sierra Nevada Hazy IPA $8.00
- Sloop Juice Bomb $8.00
- Tecate $7.50
- Victory Sour Monkey $8.00
Jake's Dilemma Details
Service options
- Outdoor seating
- Takeout
- Dine-in
- Delivery
Highlights
- Bar games
- Fast service
- Great beer selection
- Great cocktails
- Sports
- Trivia night
Accessibility
- Wheelchair accessible entrance
- Wheelchair accessible restroom
- Wheelchair accessible parking lot
Offerings
- Alcohol
- Beer
- Cocktails
- Dancing
- Food
- Happy hour drinks
- Happy hour food
- Hard liquor
- Wine
Dining options
- Seating
- Table service
Amenities
- Restroom
- Wi-Fi
- Wi-Fi
Atmosphere
- Casual
- Cozy
- Trendy
Crowd
- Groups
- Tourists
Payments
- Credit cards
- Debit cards
- NFC mobile payments
- Credit cards
Parking
- Free street parking
Jake's Dilemma Photos










Jake's Dilemma Location
Jake's Dilemma
430 Amsterdam Ave, New York, NY 10024, USA
Jake's Dilemma Reviews
happy hourbeer pongcollegecrowdbouncerginhatfratfoosballpitchers
★ 5★ 4★ 3★ 2★ 1I visited Jake's Dilemma for my Nephews Graduation/Going away event. The bar was lively when I arrived, The back section was reserved for our group. The catered finger foods that were served were good and the drinks (Open Bar) were even better..😜🥃I would highly recommend this place for an after work or weekend meeting spot.
June 07 · Ronnie CrawfordI hosted a private in the event oak room and it was fantastic. It’s a great space and the staff was amazing, food was great, and the folks I coordinated with were prompt and on it! Would recommend hosting an event at Jake’s dilemma!
June 18 · Samantha SimonsI went last night with my friends looking to have a good time, and instead, we walked out completely disappointed. Yes, the place looks amazing great decor, nice vibe but don’t let that fool you. The service was absolutely disgusting.My friend went up to the bar to order some drinks, and the bartender treated him with a nasty, arrogant attitude. He even had the nerve to ask for money just to change the music. Are you serious? I worked in the service industry for five years, and if there’s one thing I learned, it’s that customer service is everything. That guy shouldn’t even be behind a bar, let alone dealing with people.No matter how “pretty” a place looks, if the staff treats customers like garbage, it’s not worth a single cent. I’ll never come back there!
June 03 · Ilianna CruzWe (group 4) walked in and were the only people in the bar. They were playing Disney music really loud, we asked to turn it down (as we were the only customers) which the bar maid did…but then sneakily turned it back up again a few minutes later. We ordered 4 draft beers which were only ‘cool’ not ‘cold’ and didn’t taste great either.The wings we ordered were good…that’s the only thing that got these 2 stars.All in all, not a great experience.
May 13 · Terry HolmesGreat bar amazing atmosphereMet my old.soccer coach I ain't seen 40 yrs and we really enjoyed the afternoon
May 11 · Dylan Kerr
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