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Jake’s Dilemma, Popular Upper West Side Bar, Will Close After 32 Years

September 8, 2026 | 8:39 PM
in NEWS, OPEN/CLOSED
0
The inside of Jake’s Dilemma. Photo courtesy of Mark Bollettieri.

By Gus Saltonstall

Jake’s Dilemma, the incredibly popular Upper West Side bar at 420 Amsterdam Avenue, will close next month after more than three decades of business, the restaurant announced Tuesday on its Instagram.

“After 32 years on the Upper West Side, we’re heartbroken to share that we lost our lease, and Jake’s Dilemma will close its doors on October 18,” the bar wrote. “Jake’s has been so much more than a bar. It’s been late nights, game days, first dates, bad decisions, lifelong friendships, incredible staff, and more stories than we could ever fit into one post.”

The bar, located on Amsterdam Avenue, between West 80th and 81st streets, describes itself as “an old school pub vibe mixed with a downtown bar atmosphere boasting an outdoor café.” It was known for its late-night hours, sports-watching options, and dance floor.

“We still have a little time left, so come have One Last Round with us before October 18,” the watering hole added on its social media post.

Jake’s Dilemma is under the same ownership as The Gin Mill, which is located nearby at 442 Amsterdam Avenue. “And while Jake’s is closing, the party isn’t. You’ll still find us right next door at The Gin Mill, waiting with open arms.”

 

View this post on Instagram

 

A post shared by Jake’s Dilemma (@jakesdilemmanyc)

Comments on the bar’s closing announcement immediately flooded in.

“’Heartbreak’ doesn’t even feel adequate. Jake’s is significantly responsible for the life I have today: including numerous lifelong friendships, a happy marriage, and my unwavering ability to throw back a shot of Tully,” one patron wrote.

Another commenter penned, “Wow! A staple of the UWS and the BEST stretch of Amsterdam Avenue. Thank you for it All!”

West Side Rag will update this story if we can find specifics on what happened with the lease.

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