10 Almost Free Winter Dates That Are Actually Fun


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.

6. A Lecture or Screening at the Local College

Yes, everyone else will be under 21 or over 65, and yes, unless you play your cards exactly right and/or are extremely lucky, your money-saving motives will be transparent. But a few notes in defense of this one: a) college was fun, b) learning is good, c) sometimes you end up seeing very famous and interesting people, d) there is often free wine and cheese. (Check the poster for “reception to follow” to avoid dry and hungry disasters.)

7. Free Museum Nights

I know. I know. But museums are heated, and also, are full of beautiful and/or interesting things. Free nights are often packed, but on the bright side, that makes them all the better for people watching, and there is often music, so it’s pretty much a two-for-one.

8. Make Pizza

Again, flour is cheap. Sauce is cheap. Cheese is less cheap, but no need to be a gourmand here — you’re playing for nostalgia and amusement and maybe make outs, not fancy stuff. Or fancy stuff — live a little. Three buck chuck is a totally legit for this one, and it’s classy if your date brings it (pro tip for the daters), so hopefully, you can drink your backup bottle later.

9. Used Bookstore Adventure

Find a huge one — you’ve got all day — and start wandering. Get to know each other by exchanging literary histories. For example, he read The Hardy Boys: The Great Airport Mystery? You read The Hardy Boys: The Great Airport Mystery! Soul mates. She’s a Hemingway fan, you’re a Faulkner fanatic? Modernist tension is sexy. He’s really, really into Bret Easton Ellis — well, best to know now. Continue the conversation over coffee, or beers, if you’re feeling flush.

10. Bar Trivia

It’s like hanging out at a bar, but better, because it’s competitive. Teamwork brings people together, and if you win, you’ll pretty much be turning a profit (in free pitchers of beer). If you don’t win, whatever — you’ll always have your dumb team name (Bad News Beers, really, you guys?) to tell the grandkids.

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