Almost-Free Winter Dates That Are Actually Fun

We're happy to present this excerpt from one of our favorite sites, The Date Report. This season's chilly weather is the perfect setting for these fun date ideas.


Winter is the season for romance, for snuggling and warm fires and rosy cheeks and mid-blizzard dinners by candlelight. Also, the season for spending all your money, because cold-weather dating is expensive. In the summer, “exploring a new neighborhood” while “drinking iced coffee” is a totally respectable option. More than respectable — that’s the romcom date montage ideal and it also happens to cost you $8.75 or whatever two coffees go for these days. In the winter, though, that adorable aimless wandering is torture, and nobody drinks any iced coffee at all. But just because you’re snow-covered and seasonally depressed doesn’t mean you’ve got to break the bank, because while Le Cirque is absolutely a February-appropriate date option, it isn’t the only February-appropriate option. Here are 10 free (or almost free, because let’s be serious, drinks are delicious) things you can do before the slush melts.

1. Sled

This one is obvious. Child-like whimsey? Nostalgia? Clutching each other because sledding is secretly terrifying? Check, check, check. You need snow and a hill and some kind of disk or tray big enough for sitting on, but once you’ve got that, you’re set. Also, you can have hot toddies after, and while those aren’t free, sledding is a day time activity, so you can time this one for a happy hour discount.

2. Listen to Records

Employ the universal shorthand for “please come over and make out with me like we are high school students from the ’70s” and invite your date over for a night of easy listening. You need a certain level of intimacy to pull this off — specifically, a level of intimacy where it won’t be weird to have this stranger in your house and you would also like to kiss them — but you basically need nothing else. Nacho ingredients are good, probably.

3. Wander Around an (Indoor) Flea Market

A flea market is a legitimate way to take a winter stroll while taking advantage of modern heating technology. You can, and probably should, take advantage of some overpriced artisanal hot chocolate while you’re there — or secretly thermos-in your own — but otherwise, the cost of browsing is $0. This is also a good way to figure out if you’re dating a mid-century modern or a more of a Victorian type, which will be important, when you furnish your estate.

4. A Comparative Dumpling Tour

Upfront: this is not even kind of free, but it is probably the cheapest way to stuff your face and call it an event. You need a local Chinatown, long undies, and a whole lot of one-dollar bills. Then, consult Yelp, map your route, and hit up as many 5-for-$1 dumpling places as you can stomach. You can still do this for about the cost of those two summer time iced coffees.

5. Bake Cookies

Flour is cheap. Cookies are delicious. Cookie cutters encourage creativity, but do not produce the best cookies, so choose wisely.

For five more date ideas, head to The Date Report: 10 Almost Free Winter Dates That Are Actually Fun

—Rachel Sugar

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