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24 Actually Creative Date Ideas to Try This Winter

It can be a hard knock life out there for any reasonable person trying to date from November to February. The mere phrase “going out” implies some real dangerous notions about being expected to LEAVE (?) your HOME (??) to go somewhere OUTSIDE (???). Trying to find humane creative date ideas for the winter can feel like torture for those of us who don’t want to live out the plot of “Snow Dogs”. I’m tired of having people suggest the same three activities, and one of them is always ice skating. Buddy, the last time I went regular skating, there were casualties, and you want me to add ice?

It can seem like the entire dating industrial complex is out to get those of us who want love but also don’t want to lose a toe to frostbite (or worse, CHAPPED LIPS!!). So what’s a reasonable person supposed to do? The same date activities as the rest of the year, but while wearing a coat and a scarf or something? Of course not! What you need is special, winter date ideas for the perfect wintry date that you can do in the winter, all winterly.

Dating in the winter actually has a lot of advantages, if you know where to find them. It’s the season where drinking a cup of chocolate is most socially acceptable, you can snuggle without getting sweaty, and every public space gets about five times as photogenic in anticipation of the Imminent Holidays.  With cuffing season in full swing, the dating world can be your oyster for encounters worthy of a Hallmark movie (minus the part where you have to give up your job as the VP of Marketing for EvilCorp to marry a lumberjack named Chris Mass back in your old hometown). Let us take you through our idea of a good wintry time, and you’ll be full of warm fuzzies before you know it!

1. Build A Snug Empire

Spend an afternoon building the most extra blanket fort to stave off the chilly weather.

2. Mini Movie Night

Get a mini projector, some movie theater candy and popcorn and a blanket. Host a cozy movie night in your own home.

3. Go Digging For Personal History

Go through your pockets, bags and drawers looking for mementos—what you find, tape together in a collage or scrapbook page.

4. Fantasy Vacation Planning

Each of you research your dream getaway and try and sell the other person on your daydream adventure.

5. Family Portrait Time

Hang up a sheet, get some props from a dollar store, and have a little fun in your homemade photo booth! Get a disposable camera (or just re-download Huji) and make an afternoon out of it.

6. Chef It Up

Pick a family favorite dinner or dessert recipe and really try to nail it.

7. Spa Day

Pick up some fancy bath supplies or massage oils, light some candles and try to find a copy of that CD every massage place has that’s just bird noises over Mozart.

8. Double Feature

Spend the day at the movies—grab a meal after movie one and then head back for seconds!

9. Become Chocolatiers

Give yourselves 20 minutes in a nearby grocery store to collect random ingredients and then see who can create the most impressive hot chocolate out of them.

10. Have A Terrible Sweater Moment

Head to the nearest Goodwill and find the worst sweaters you can. Best case you’ll be prepped for this year’s obligatory Ugly Sweater Party but at the very least you can kill a few wintry Sunday hours.

11. Lit Love

Go to a bookstore, locate one (or more) of your all-time favorites and swap them. Find some comfy chairs, hunker down, and enjoy an afternoon discussing your picks.

12. Get Crafty

Head out to a craft store and pick out the first kit that seems interesting. Spend a few hours painting models, making sand art, braiding friendship bracelets or trying your hand at sculpting. And when you’re done, you’ll have a (probably bad looking but still sentimentally important) craft to remember your time!

13. Indoor Scavenger Hunt

Grab a pack of plastic easter eggs(or any other smallish object) and label each with a compliment, secret, or coupon for a service 😉 Hide them around your home and dare your date to find them all!

14. Resolution Binge

If either of you have resolutions you’ve been dragging your feet on, try and help each other get them done—whether it’s cramming in 10 hours of Duolingo or trying to do even a single handstand (me). It’ll be more fun with a little support!

15. Shopping Sprint

Head to the mall or the closest trendy downtown strip and help each other find gifts for their friends and family. You’ll get to learn more about each other and avoid the last-minute gift scramble of Dec. 22.

16. Smell The Roses

Take your date to the nearest nursery (the plant kind; not the baby kind) with an indoor section and soak in that light, humidity and plant smell as you wander. You can even pick up a small succulent or houseplant to remember the day.

17. Family Favorite Movie Marathon

Host your own private film festival—the theme is holiday movies you grew up with. Enjoy snuggling in a sentimentality coma and maybe even find a few new favorites.

18. Resort Gatecrash

Find a nice hotel nearby with a big fireplace. Pretend to be guests and sprawl in front of the fire all evening long—maybe even order a few hot toddies for extra coziness.

19. Get Your Cuteness Fix

Visit an animal shelter on an adoption day, or better yet, volunteer! You get all of the pet cuddles with zero of the longterm responsibility of pet ownership—talk about a good time!

20. Go Back To School

Find a community class for something that sounds interesting to you both—flower pressing, hot yoga, or creative writing. You get to spend some time indoors and build a skill together!

21. Pop In For A Pop-Up

Look up local events in your area and mark your calendar for winter markets. Best case, you two get to knock a few gifts off your list and support local artists. But no matter what, you’ll get to spend a few hours perusing!

22. Get Competitive

Pop into your nearest Goodwill or Dollar Store and pick up some games that 1. are completely unfamiliar and 2. look insane. Enjoy a night in with the beverage of your choice as one of you discovers a new knack for whatever “Telestrations” is.

23. Support The Arts

Find a community theater production of something that sounds interesting—enjoy the warmth, low ticket price and triumph of the human spirit that is the heart of local theater.

24. Museum Crawl

Look up obscure museums or even popular ones you haven’t gotten around to yet. Try to fit as many as you can into an afternoon or just spend the day discussing three paintings. The whole time, you’ll be avoiding the snowpocalypse AND feeling cultured as hell.


A version of this article was published in 2018.


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