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Jake's Dilemma

4.0(1,533)
Sports Bar

About

Jake's Dilemma offers a lively Upper West Side setting with 19 drafts and over 35 bottled beers, including microbrews and craft selections. The venue features an old-school pub vibe with an outdoor café, foosball, beer pong tables, and live entertainment during the week and weekends.

For business events, the venue provides three private spaces: The Oak Cellar with European-inspired charm and a private bar, the cozy Riverside Room tucked away from the main bar, and The Commons, a communal area with exposed brick and hardwood floors that balances privacy with access to the lively main space.

Best for

  • Casual team happy hours
  • Informal client socializing
  • Small group celebrations with games

Request a Package

Tell the venue what you're planning and they'll respond with a custom proposal within 1–2 business days.

Group Dining Event

Custom request

Perfect for team dinners, client lunches, and celebration meals. Reserve a private or semi-private space for your group with food, drinks, and AV if needed.

What's typically included

  • Private or semi-private space
  • Food & beverage
  • AV & technology

Happy Hour

Custom request

Host a relaxed evening reception for your team or clients. Reserve a space for drinks and light bites in a social, low-key setting.

What's typically included

  • Private or semi-private space
  • Food & beverage

Full Buyout

Custom request

Take over the entire restaurant for your event. Full control of the space, menu, and atmosphere — ideal for large celebrations or exclusive corporate events.

What's typically included

  • Full venue layout
  • Food & beverage
  • AV & technology

Venue Details

Standout features

Beverage Selection
Extensive draft and bottled beer variety
Offers 19 different drafts and over 35 bottled beers including microbrews, lagers, ales, seasonal, and craft beers, catering to a wide range of tastes.
Private Event Spaces
Three distinct private rooms with unique character
Includes The Oak Cellar with European-inspired industrial charm, the cozy Riverside Room with decorative floor tiles, and The Commons featuring exposed brick and hardwood floors, providing versatile options for business gatherings.
Outdoor Seating
Outdoor café space
An outdoor café area provides an alternative setting for guests, adding flexibility and fresh-air options for events.

At a glance

Rated 4.0 on Google · 1,533 reviews