5 Quirky Date Night Destinations near Penn Station, NYC

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Date night doesn’t have to be the same each time. While we all love cuddling up at the movies or trying new restaurants or embracing a bit of high culture at museums, every once in a while, date night needs to be shaken up. Each city has a hidden world of strange, quirky, and delightful things to do. Try any one of these on your next date night and embrace the weird, whimsical part of life.

The Drama Book Shop

Feel like embracing the New York City theatre scene while also unleashing your inner reading nerd? If so, then head to The Drama Book Shop, a staple for all artists and theatre enthusiasts. It has recently been renovated to resemble 20th century European cafes, so now you and your date can peruse the book racks after stopping at their full service café. Make a scavenger hunt out of your visit (who can find the most unusual, wackiest play?) or read to each other from the poetic language of drama. 

OMEscape Room

Escape Rooms have become popular date night activities because it is outside the typical wheelhouse of date night ideas. At OMEscape, you’ll love solving the puzzles and challenges required to escape and have a chance to choose from several adventures. Try “The Penitentiary” and try to escape one of the most infamous military prisons in history or become a time traveler desperate to save your travel companions in “Room X”. 

The McKittrick Hotel

What was once a warehouse is now a 5-story pseudo hotel, home to one of the strangest collections of interactive performances in New York. On one floor, the famous “Sleep No More” show takes place (where Shakespeare’s Macbeth is told through a film noir lens) while on another floor you’ll discover Gallow Green (a forest in the hotel). Everywhere you turn in The McKittrick Hotel, you’ll see some oddball setting or performance happening. Part of the fun is the way that The McKittrick Hotel is unapologetically itself.

Frames Bowling Lounge

Only New York City would have a classy, slightly upscale bowling alley like this, where not only can you go bowling but you can also play ping-pong, billiards, shuffleboard, or any number of classic date night activities. But what really sets Frames Bowling Lounge apart though is the atmosphere. Each activity has its own themed room. You can walk from the sleek, modern bowling lanes to the rustic, dimly lit billiards lounge to a “summer seascape” with palm trees, Adirondack chairs, and ping-pong.  


New York City is famously one of the most diverse cities in the United States. There is Little Italy, Chinatown, Harlem, and more. So why not take a spin through a lesser known ethnic enclave for date night and throw in a lot of delicious food? There are plenty of places to buy Korean BBQ, colorful rice cakes for dessert, Korean groceries, books, tchotchkes, and more. The heart of Koreatown, on W 32nd St between Fifth and Sixth Avenue, has the ambience of the city of Seoul itself. A visit to Koreatown is like taking a mini vacation to Korea.

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