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Well, we’ve reached cuffing season. And let me guess: You’re in need of some ideas for winter dates to cure your cabin fever. Whether you’re looking for things to do with someone new or trying to find something different for the person you spend all of your time with, it’s crucial to find an activity that’s fun and romantic, and won’t wreak havoc on your bank account.
And if you’re actually not in the mood for any of that? These winter dates also double as a good outing with a best friend or a long-lost cousin you’re dying to reconnect with. If we’ve learned anything from the past few years, it’s the importance of spending quality time with the people you love most, be that love romantic, platonic, or familial! Fun date ideas are for all.
We asked Glamour editors and a few dating experts for some fun, easy, and cheap winter date ideas that, at the very least, will occupy you until it’s time to crawl under the blankets again.
1. Take a walk through the snow.
This is Lorelai Gilmore’s favorite thing to do, just sayin’. When the snow starts falling, grab your partner and get strolling before it gets too icy. Just bring a thermos of coffee or hot chocolate or stop at a local café along the way to warm up as you go.
“My husband and I love long walks as a date, no matter the season,” says deputy editor Anna Moeslein. “We'll pick a direction at random and just see where we end up—the only goal is to stop at a coffee shop or restaurant along the way. It's a nice way to connect. With no screens out or other distractions, there's nothing to really do but have a heart to heart.”
2. Try some DIY karaoke.
Karaoke is one of the most fun things you can do with your pants on. (And thanks to the magic of the internet, it’s also doable over Zoom if you’ve got a long-distance love.) Put the lyrics and backing track on your laptop, then belt it out like you’re all in the car with James Corden. Nothing brings people together like making fools of yourselves.
“During the pandemic, like everyone else, my husband and I had to get crafty, and one of our favorite activities ended up being doing at-home karaoke (much to the chagrin of our neighbors)," says Glamour’s commerce director Brie Schwartz. "We’d fire up the lyrics to, say, RENT on YouTube, stream it to the TV, whip out our mics, and watch the hours slip away. It’s still one of our fave free Friday night activities.”
3. Get creative around town.
This also works as a great first date idea. Check out the holiday window displays in department store windows, or make a reservation to see a museum exhibit. Concert halls and movie theaters are also good, but that doesn’t mean you have to spend a ton of money to get your yearly fix of culture. Murals and sculpture gardens are outdoors and, best of all, free! “The museum stroll is a classic date activity that's even more fun in the winter as a respite from the cold,” says senior visuals editor Lauren Brown. “Most museums have new programs this time of year, and it's a great way to stay inspired and stimulate some intelligent conversation with your special person.”
4. Embrace cookie season.
If you aren't already totally sick of holiday baking, have a bake-off or try your hand at decorating with icing and sprinkles. And if you are over it, now you have an excuse to buy 12 boxes of Girl Scout cookies at a time: It’s going to support young kids! Make a blind taste test out of it—think your person can guess which flavor it is?
5. Pretend it's summer.
Instead of embracing the winter wonderland around you, find a way to bring a little summer sun back into your life. Go to a tiki bar and order tropical drinks, or even plan a getaway to a beach if your budget allows.
“I always like counter season dates,” says Yue Xu, a relationship expert, cohost of the Dateable podcast, and coauthor of the upcoming How to Be Dateable (out January 28). “If it's winter, and it's really cold where you are, go somewhere. Can you do something that's warm? Is there a beach-themed place that you can go to that brings you back to summer?”
6. Invent a new recipe.
We all love big Sunday brunches, but sometimes a noisy restaurant isn't really the best place to catch up. So, make your own breakfast spot at home! Take whatever you have in the refrigerator and see what you can each come up with. If you need a little inspiration, we found some pretty genius brunch ideas for you.
7. Netflix and chill? Still totally an option.
Look, it’s a classic for a reason! We recommend the two of you cuddle up on the couch and get invested in some prestige TV. We’ve got loads of recommendations for what to stream on Netflix next. We’ve also rounded up the best winter movies and the sexiest movies, so you really have no excuse for “idk, what do you wanna watch?” To set it apart from any other night, turn your living room into a makeshift theater with an indoor picnic.
8. Make Alex Trebek proud.
Honor the late, great game show host by planning your own trivia night with friends in a couple versus couple competition, or just let an old Jeopardy! episode play and make a game out of who can guess the most right answers before the contestants.
“Jeopardy is the best thing to happen to streaming in a longtime,” says Glamour senior editor Sam Reed. “My boyfriend and I totally take advantage. Some spinach and artichoke dip, a warm beverage (or three), and we're set for hours.”
9. Take advantage of the cold with some romantic ice-skating.
For some reason, it seems one person in every relationship is good at skating and the other one falls every other minute. Go ice skating anyway. You can use it as an excuse to hold each other tighter, and don’t be put off by the 10-year-old doing spins in the center of the rink. That kid has nothing to do with you.
10. Get a little buzzed.
A wine-of-the-month club never seemed like such a good idea. You can try mixing one of these winter cocktail recipes from your home bar cart, or turn doing the dishes (the never-ending dishes!) into some kind of drinking game. (“I like to make mulled wine in the winter,” suggests Glamour senior editor Stephanie McNeal.) The one benefit of getting lit at home is you don’t need to worry about paying for an Uber after last call.
If you do want to get out, consider a brewery, distillery, or winery tour. “Even if you're not a big drinker, a brewery tour is a fun date activity,” says Brown. “It combines all the great elements of a fun date: discovery, walking, and learning. Normally, there's a great selection of beers to try and delicious light bites as well.”
11. Have a themed cuisine night.
Cannoli and The Godfather. Chocolate and Chocolat. Ratatouille and Ratatouille. Order (or make) a dish you’ve been meaning to try, and do a movie night that’s somehow related to it, whether by location or as part of the plot. You can even dress up and listen to thematically related music. It’s a night in Paris without the hassle or the expense.
12. Take a food tour around the globe.
You don't have to leave your hometown to experience global cuisine. “My husband and I spent one winter doing a food-around-the-world challenge,” says Moeslein. “Every weekend, we'd pick a different cuisine and find the most authentic dish we could try, whether that was from a restaurant or with a recipe we made at home.”
Live in an area without diverse food options? Moeslein also recommends the Universal Yums International Snack Box, which sends treats from around the world every month. “We always look forward to our Yums box,” she says. “We make a game out of guessing the flavors and ranking our favorites.”
13. Get crafty.
Color us corny, but we love all the wintry crafts. Make a gingerbread house together or bust out the old protractor and cut out those six-pointed paper snowflakes we all made in middle school. Knit each other scarves and hats and mittens to stay cozy all winter long. You’d be surprised how easy it is to get into a deep conversation when you’re also doing something with your hands.
14. Have a snowball fight.
Some more cold weather date ideas! If you can’t beat the cold, embrace it. Get a sled and hit the park, make snow angels and pelt each other with snowballs…roll up a snowman too. As long as it’s light out, make the most of the outdoors. Brown likes snowtubing during this time of year. “It's way more accessible than learning to ski or snowboard,” she says. “And you can have a nice warm cocktail after.”
15. Throw a mini concert.
Did you learn to play the guitar recently? Even if it’s only “Wonderwall,” your date wants to hear it, because there’s nothing like live music. If neither of you are instrumentally inclined, throw an indoor dance party with a favorite playlist or stream a live concert together and pretend you’re at a venue. Hey, no line for the bathroom.
16. Powerpoint night.
Works best with groups of friends or multiple couples. You’d be surprised what people come up with! You can have everyone present on the topic of their choosing, or make it a self-referential activity. We’ve seen everything from “What kind of potato everyone would be” to “My friends as explained by Taylor Swift songs.”
17. Have sex.
Listen, it’s been a hard couple of years. It’s okay to need some physical intimacy. And maybe you mix it up with one of these kinky sex ideas.
“For people that are adventurous, you could try heated seat car sex,” suggests Dr. Tara Suwinyattichaiporn, a sex and relationship expert, the cohost of Celebs Go Dating, and host of the podcast Luvbites by Dr. Tara. “Car sex is exciting and can really show that hot, in-the-moment passion for your partner. Even for people in long-term relationships, changing up where you have sex from the bedroom to other places—like the car—can be a good way to bring more passion into your relationship. And because it's winter, the heated car seat will make it even more warm and comfortable and fun.”
18. Take in the lights.
Whether it’s past your neighbors’ houses or downtown, take a drive around and look at the holiday decorations. As a bonus, you can take notes for your own decor. You can still do this date once January hits too: Many parks, zoos, and botanical gardens across the country offer outdoor light shows well into the new year. “The temperature may be dropping, and it's honestly tough being outside, but grab your handwarmers and get down to your local botanical gardens if they have a lightscape walk,” says Brown. “It's a fun excuse to cuddle up as you walk through.”
19. Have a couples-themed photo shoot.
Matching pajamas, costumes, totally glam…the possibilities are endless. Plus, you might even get a Christmas card for next year out of it.
20. Build a gingerbread house.
Ah, the winter equivalent of pumpkin carving. Honestly, making gingerbread houses is probably the most wholesome holiday activity. Warning: Some assembly required.
21. Do some bartending.
Take a bartending course, or have a contest at home to see who can make the most creative cocktails or mocktails. If you’re not sure where to start, here are some Glamour-approved winter cocktail recipes.
22. Go sledding.
When it comes to fun winter date ideas, there’s nothing wrong with connecting with your inner kid! You can always “Cheers!” over a thermos filled with spiked hot chocolate or cider after the sledding adventure is over.
23. Cozy up by a fire.
Cute winter date ideas don’t have to involve leaving the house. If you have a (working) fireplace at home, build a fire and enjoy the cozy vibes with a hot beverage like hot cocoa or mulled wine. S’mores are optional but encouraged. If your home isn’t blessed with the luxury of a working fireplace, head to a nearby bar or restaurant that has one and soak up the holiday hygge there. Fireside chats are the best.
24. Go to the market.
Your local craft fair or farmer’s market will have some of the best gifts for those you love and yourself, and it’s a great opportunity to support independent artists and small businesses. Or just shop for yourself—you’ll find some unique arts and crafts as well as delicious local food and drinks.
25. Trivia night (IRL)
Test your knowledge as a twosome (and without the help of your friends) by attending a trivia night and competing as your own team of two. Trivia is one of the most underrated indoor activities of all time. Most trivia nights at bars or restaurants are not only fun, but free with the purchase of food or drinks.
26. See live theater.
Whether it’s the annual local production of The Nutcracker or a community theater performance of a play you’ve never heard of before, go see some live theater. Get all dressed up in one of these winter date night outfits and grab a nice dinner beforehand to make a whole fancy night out of it.
27. Check out every holiday display in town.
Most towns across the globe have a plethora of holiday decorations for Christmas, New Year’s, and Valentine’s Day. Even if you’ve lived in your town for a long time, you might have missed some of its best decor. Make a map to follow and visit every display in town for a fun adventure close to home. Cities like NYC and Chicago already have everything mapped out for you, but it might be fun to make your own anyway.
“While it can be stressful, I personally think the holiday season can be really romantic,” says Julie Krafchick, a relationship expert, cohost of the Dateable podcast, and coauthor of the upcoming How to Be Dateable (out January 28). “There are a lot of really fun and whimsical types of activities that don't present themselves other times of the year. There is a life-sized gingerbread house in the city I'm at, for example. Things like that can be fun, interactive experiences you can do together.”
28. Have a romantic spa day.
If you have the budget, schedule a couple’s massage or buy two day passes to a spa or bathhouse. Too expensive? No problem! Make a plan to meet in your gym’s coed sauna or take turns giving each other a massage at home.
29. Go on a real-life treasure hunt.
Explore thrift stores, antique malls, or garage sales together and see what unique finds you discover. Find a cool secondhand outfit for your partner to wear to dinner that night, challenge each other to see who can find the most interesting item, or create a scavenger hunt and whoever gets the most on the list wins.
30. Game night—with a twist.
You can’t go wrong with a classic board game night—it’s free, it’s fun, and you have easy access to all the drinks and snacks at home. Or you could mix it up and try one of these sex games for couples. Thank us later.
31. Learn something new together.
Sign up for a cooking class, find a free online course for something that excites you both, attend an interesting lecture at your local community center, or treat each other to foreign language lessons—whatever it is, you’ll have something new to talk about at the very least.
32. Play some games.
This classic first date option still works even if you're deep into your relationship. Find a local bar with pinball machines or a game-centric place like Dave & Buster's and let loose.
“I went on an arcade date with a guy I really liked once, and we had the best time,” says senior beauty editor Ariana Yaptangco. “Playing arcade games taught us a lot about each other: our level of competitiveness, our methods for problem solving, and how playful we can get. And before you cringe at the idea of kids running around to ruin the mood, we made sure to go to an adults-only arcade with drinks and light bites. It was a great way to go out but stay in during the cold winter.”
33. Go bowling.
Sure, the shoes aren't sexy. But just like arcade games, anything that involves a little friendly competition can help heat things up. “Bowling is my favorite date activity, and it's perfect for a first or second date,” says senior analyst Loneeja Talukdar. You also don't have to be pro-level to get into it. “While beginners might need some time to get the hang of it, with enough rounds, you can start to pick up the basics of the game.”
34. Have a movie marathon.
There are so many ways to have fun with this: Pick an actor or director you both like, and watch all of their films. Select a genre you want to explore and go deep. Or spend a whole day with an entire movie series like Fast and the Furious.
“I love doing a curated movie night—or movie nights, I should say—in the winter months,” says Moeslein. “We'll order takeout, open a bottle of wine, and just settle in for our movie marathon.”
35. Climb new heights.
Working out on a date is not for everyone. (So much sweating!) But if you are open to it, indoor rock climbing can be fun and a way for you to try a new challenge together. “I recently started indoor rock climbing,” says Talukdar. “It was my boyfriend's idea for a date. It requires a lot of upper body strength, and it's definitely not as easy as it look. But it's a great idea if you're looking for a fun activity that brings you and your partner closer together.”