New York Dearest
The guide, $35
A place · Bar · Upper West Side · on 1 of my list

Jake’s Dilemma.

Worth it, says Antonina. Jake’s Dilemma is known for inexpensive drinks year-round but the deals get even better during happy hour with $5 beer, well drinks, and shots (top-shelf well drinks clock in at $7).

Antonina Pattiz
Antonina PattizI went myself · from my Best happy hours on the Upper West Side
Where Jake’s Dilemma appears on New York Dearest

It's on 1 of my list. Each entry below is what I wrote about it there, with my verdict on that list, the fullest first.

Best happy hours on the Upper West Side

No. 7 on that list2 min from the subway
Worth it
  • Cost$5
  • Subway1 to 79 St, 2 min
  • Address430 Amsterdam Ave, New York, NY 10024
  • Health gradeA, city inspection
  • From my guide, updated September 2026.

Jake’s Dilemma is known for inexpensive drinks year-round but the deals get even better during happy hour with $5 beer, well drinks, and shots (top-shelf well drinks clock in at $7).

Keeping things interesting, Jake’s Dilemma also runs post-happy hour specials weekdays from 7pm to close. With $17 pitchers on Mondays and $10 beer + shot combos on Tuesdays, you’ll be content for a while.

Read it on the list
Worth it, says Antonina. Been? Say if you agree.
Jake’s Dilemma

Nearby, from my lists

Worth it, within a ten-minute walk
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Jake’s Dilemma

Upper West Side