The Holiday times naturally bring togetherness and the warm feel of romance, but when lounging by the fire gets old, there’s a whole city out there full of festive activities. Whether you are one who enjoys cheesy traditions, or you prefer unique anti-celebratory events, it’s always a joy to get winterized with your date. -Liz Levine
1. The America Museum of Natural History
Dateworthy any time of year with its countless conversation starters and parkside location, the Museum of Natural History is full of special draws come holiday time. For those who appreciate the intricate craft of origami, or those who simply enjoy really large trees, there’s the Origami Holiday tree, decked out with over 1,000 finely-creased pieces of colored paper in the shape of the museum’s famous attractions. See how many dinosaurs your date can identify from the prehistoric array surrounding the bottom of the tree. Your brains properly challenged, move on to the automatic romance that comes with an ice skating rink, this one boasting a giant, light-covered polar bear and environmentally friendly synthetic gliding surface. The affordable $10 cost means there will be plenty of cash left over for hot coco at the adjoining café.
2. The Pond at Bryant Park
Squeezed into Bryant Park’s bit of Midtown oasis, The Pond is the most urban rink in the city, with office buildings and hotels towering overhead as you glide along. The free entrance makes it ideal for enthusiasts who have their own set of skates, but the reasonable $12 rental come with the delightful awkwardness that non-serious skaters bring. Is there anything more romantic that grasping your date’s hand as you lose your balance, or casually clinging to their arm in an attempt to keep your clothes dry? Don’t forget that ice scraped up with your mighty blades may be used to make snowballs for some playful teasing, though you may suffer the wrath of the zamboni guy. Check out Bryant Park’s website for a long list of skating-related activities like ice dancing performances and other bits of fancy, or come any ‘ol time and browse though the many holiday shops.
3. Santacon
For those who find drinking and dating to be the perfect mix, look no further than Santacon (pictured, above), the borderline alcoholic’s chance to spend a whole day with thousands of intoxicated Santas. The annual revelers are serious about their celebration, beginning the day promptly at 10AM and traveling in an unruly group throughout the city, stopping at bar after bar after bar. Costumes are mandatory, as is you sense of adventure – the starting location is not announced until the evening before the event, and each person is responsible for keeping just aware enough to stay with the group. Such dedication to life, laughing, and fun will show your date your jolly side, as will your fuzzy red suit and easy excuse for lap sitting. In no time at all, the conversation will flow and easily as the beer. This year’s Santacon was on Saturday, December 13th. Elves, reindeer, and drunken abandon welcome.
4. Shop
Everyone has a list of people in their lives that require gifts come holiday time, but the kindly spirit of giving if often overtaken by the bustle, hassle, and madness of shopping. Take your date over to Williamsburg for the Artists & Fleas market for one-of-a-kind artsy items and handmade crafts. Local artists gather during their extended holiday hours to offer gifts your friends and family won’t find anywhere else such as T-shirts and clothing, jewelry, beauty products, dolls, toys, and many other items. Get a feel for your date’s crafty side as you snack on homemade baked goods and browse the city’s creative output. The space also boasts a large selection of vintage clothing and used records and books, so you’ve got the “something for everyone” covered as you riffle through treasures with your date.
5. Watch Something
Taking advantage of one of the city’s cultural attractions is a fine plan for any date, and when the holidays are in full swing the possibilities are endless. Those into tradition will enjoy the Radio City Christmas Spectacular, where customary Christmas moments are celebrated with much showiness and magnificent stage production. High-kicking pretty ladies and men prancing around as toy soldiers will warm the heart and fill you with nostalgic tales of home. For couples who cringe at showy celebrations, head to the Landmark Sunshine Cinema for midnight screenings of Black Christmas. A film classic since 1974, it offers the endless entertainment that is a terrorized sorority house plus all the natural joy of Christmas. This cheesy slasher is a far better choice than the myriad holiday feel-good films that our families have been dragging us to for years. If you’re more in the mood for a rock concert, Yo La Tengo’s 8 Nights of Hannukah is a sure winner — the indie favorites will play holiday-themed shows at Maxwell’s with special guests.
6. Holiday Drinks
For those who enjoy a good drink, many bars throughout the city offer tasty wintery beverages and the cozy atmosphere daters prefer. For foodies and socialites who dig a fancy hot spot, head to the Irving Mill for a taste of The Harvest, a buzzworthy recipe containing rosemary vodka and fresh cranberries, or the sugary Sugar Plum. Williamsburg’s infinitely more laid back Sweet Ups offers cozy booths and an unexpectedly varied drink menu featuring gems like the Pink Russian and the Blackberry Bramble. Sure a regular ‘ol bar date may seem a bit cliché, but it’s a fact that lots of things are extra happy and fuzzy when winterized, and alcohol is no exception. Tell tales of family tradition and childhood mischief at Huckleberry Bar over their delicious Hot Buttered Rum or Hot Chocolate spiked with the shot of your choice.
7. The South Street Seaport
Always a romantic destination with its seaside location, old-timey ships, and dazzling skyline view, the South Street Seaport goes all out for the winter with a giant lighted tree to remind you and your date of a certain holiday. The real draw, however, is the regular performances from the Big Apple Chorus, a bunch known for their fun-loving, engaging demeanors. Plus, sometimes they wear funny costumes. Take your memory for a spin as you realize you don’t remember what you did yesterday, but that the details of all twelve days of Christmas are still fresh in your mind. Impress your date with a thoughtful rendition of “Chestnuts Roasting on an Open Fire,” though you may have to ward off invitations to join the choir. Everyone loves a free performance, and as chilly winds blow from who knows not what parts of the vast ocean, hold your date tight.
8. Bronx Zoo Holiday Lights Festival
Adorable zoo animals can melt almost anyone’s heart, but what happens when they come in the form of animated light sculptures? Romance! The Bronx Zoo is adorned at holiday time with over 140 glowing animals, adding some zip to the traditional adorned house or tree (though they so also feature tons of lighted trees). Bundle up and stick close to your date for a night of wandering around the facility’s vast grounds and seeing who can correctly identify the crafted creatures. As a bonus, certain regular zoo attractions will be open late, including the popular Monkey House. The holidays are a time for reflection and appreciation, and those scamps sure do remind us to laugh at ourselves. As you hold your sweetie close during the special night time sea lion feeding, appreciate the beauty of nature and of blossoming romance.
9. Holiday Karaoke
A great way to get to know someone a little better is to mix several social activities into one crazy holiday party. Discover the activities at which the object of your affection excels — be it singing, dancing, or even just drinking — at The Bell House’s 1st Annual Holiday Karaoke & Dance Party. This new bar and music venue offers a fine drink menu of cocktails named after famous albums, and a large performance space that maintains a cozy feel. Humble yourself in front of your date by performing your favorite holiday tunes, and then transition smoothly into a winner on the dance floor. DJ Christee, aka Of Montreal’s Kevin Barnes, will add a bit of celebrity flavor to the air, as will the hilarious comedy of Dave Hill and Eugene Mirman. Hot new club, karaoke, and famous people? You can’t go wrong.
10. Lights and Trees
Though a trip to Midtown might seem far from romantically appropriate, every holiday season deserves a bit of revelry in “Miracle on 34th Street”-style festive fun. This dense ‘hood is full of some of the city’s most famous and memorable landmarks, and though often packed with tourists, they remind of classic films and evenings spent by the fire watching them. Head over to the bustling yet gorgeous Grand Central Station for their Holiday Kaleidoscope Light Show, where ever half hour a themed display bounces off the walls and ceiling of the famous dome. There won’t be Pink Floyd music playing, but the moment will be lovely just the same. Then stroll over to the even more famous Rockefeller Center Christmas Tree at 30 Rock, where throngs of ice skaters and shoppers can’t put a damper on the utterly giant sparking spruce.
Liz Levine lives in Brooklyn and is the co-founder and co-editor of lizandlaura.com where she writes about music, pens poetry, and covers a number of humorous topics. Her work also appears at thestonewailer.com.

