Valentine’s Day weekend is the perfect time to visit some of NYC’s vintage restaurants or hidden bars  with friends or a loved one. With Presidents’ Day falling on Monday, the long-weekend is also a great opportunity to try something new or unusual. It’s not hard to create a more offbeat or even eccentric holidays here in New York City; if the classic dinner-and-a-movie combo doesn’t sound appealing this year, then check out one of these quirky Valentine’s events!
For a night filled with humor, drop by The Rejection Show in Brooklyn. The show is a comedic event centered around the rejected material of artists, writers, and comedians. Watch the Emmy Award-winning host, Jon Friedman, create a heartbreak haven by turning pain into laughter.
2. Masquerade Ball
Add a little mystery to your evening at the Down Town Association, New York’s first private Victorian clubhouse. This Valentine’s Day, the DTA will be transformed into a 1930s Parisian cabaret hall for a Masquerade Ball. Bring your vintage or period costume attire and definitely a mask! This event is great for both couples and single guests. Here’s a taste of the romantic vintage jazz music set to fill the night.
3. Literary Speed Dating
We’re not supposed to judge books by their covers, but Housing Works is going to allow it on Wednesday, February 12th with its Literary Speed Dating event. Books are the perfect icebreakers, so bring your favorite along with you to this Valentine’s event. Chat with fellow bookworms over a glass of wine or a beer; afterward, the party continues at a nearby bar, Botanica.
4. Match-Maker Heart
Young Projects, a Brooklyn-based design studio, is the driving force behind this year’s Times Square Valentine’s Heart called Match-Maker. The sculpture presents 12 different viewing points that are somehow correlated to the viewer’s zodiac sign. Peer through these intricately woven periscopes and see potential ideal astrological mates! Above all else, Match-Maker is a beautiful representation of how incredibly complicated and convoluted matters of the heart can be. Take note that weddings will be performed throughout the day in front of the sculpture this Friday.
5. Clinton St. Baking Company Pancake Month
Clinton St. Baking Co. is famous for its breakfast, brunch, and, more specifically, its pancakes. February is “pancake month” at the bakery, and they’re offering new and creative flavors every week! Start your day off with a Valentine’s special pancake, topped with chocolate chunks, fresh raspberries, and raspberry-caramel sauce.
6. MTA Missed Connections
The New York Transit Museum’s fourth annual Missed Connections party will take place on Friday at 6:30pm in Downtown Brooklyn. Brooklyn Brewery is providing beer, and there will be food, drink and raffle prizes from Boylan Bottling, Brittle Barn, Brooklyn Winery, The Chocolate Room and Nunu Chocolates among others. Beyond eating and drinking, you can make Valentine’s crafts, decorate cookies, and check out a 1936 decommissioned subway station!Â
7. Muppet Vault
This Wednesday, spend a romantic evening with Kermit the Frog and Miss Piggy. Union Hall in Park Slope, Brooklyn is presenting a night full of love-themed clips and songs from the The Muppet Show and Sesame Street. The venue was converted from a warehouse and is known to give off a library-meets-bar feel. Union Hall will also host the popular “Love Bites: The Power Ballads Sing-Along” show on Friday, featuring an air guitar competition and a costume contest.
8. Between The Sheets Poetry Brothel
For only $1 admission, spend Friday night at The Poetry Brothel’s Valentine’s Day red-light district window parlor. The Happy Bones cafe on Broome street will temporarily be transformed into an immersive window parlor, including five poetry whores in the window and a calligraphist body painter who will write lines of verse upon attendees.
9. The McKittrick Hotel
The McKittrick Hotel is known for housing the spooky interactive work of theater, Sleep No More. The hotel is also home to a great restaurant and bar: The Heath. This Valentine’s Day, a special three-course dinner is available at The Heath, accompanied by a jazzy, funky quintet called Heathens. Afterward, around 2am, the romantic People Vs. Larsen will take the stage. Don’t miss out on a night of classy drinks and good music!
10. The Players Club
The Players Club is hosting a party this Friday featuring open bar, poetry open mic, buffet dinner and dancing with the Tedd Gottsegen Swing Quartet. Here’s your chance to step back in time inside this gorgeous Gilded Age members only club. Tickets here.
Bonus: House of Cards Against Humanity
The much renowned television drama House of Cards will mark its return on Valentine’s Day! 13 new episodes will hit Netflix this Friday, so—single or otherwise—be prepared to spend most of the night in bed. This show has been building anticipation all year and will probably continue to do so, as the Netflix original series starring Kevin Spacey has already been renewed for a 3rd season. Now there’s even a “House of Cards” Against Humanity Expansion Pack, to add to the fun.