30 Winter Date Ideas for a Hotter Cuffing Season
Oh hi cuffing season, didn’t see you coming! Whether you’re already cuffed and committed, still vetting your options, or happily hooking up and keeping things casual, dating in the winter just hits different. Sure, the colder weather and limited daylight may cool down the sexy spontaneity of a summer fling, but they’re also part of what makes winter prime time for dating-dating. Between cuddling by the fireplace, long nights in, and the general coziness in the air, the colder months have a way of channeling all the romantic vibes.
Whether you’re someone who likes to get dressed up and hit the town, stay in for a cozy at-home date night, or get outdoors and brave the cold with your cuffing season partner, winter definitely does not have to mean resigning yourself to months of Netflix, takeout, and couch cuddles (unless of course you want to, in which case that sounds delightful, actually). While some of your warm-weather go-tos may be off the table for the season—bye-bye beach dates—many of your fave date-night activities are more than capable of weathering the transition (they just might require bundling up in a few extra layers).
Not to mention, winter happens to serve up plenty of seasonal dating specials of its own that are best enjoyed during the colder months. Summer may have a reputation for sultry sexiness, but those long winter nights can still bring some serious heat. To help you make the most of what is arguably the most romantic season, here are 30 winter date ideas perfect for turning up the heat on your love life even when temps are down outside. Prepare to get cozy.
1. Put up holiday decorations
I mean, not only do you get to stay inside for this and keep your comfy clothes on, but you get to decorate your apartment or place together. Maybe it’s putting ornaments on a tree, maybe it’s putting up that “what a wonderful world” sign. Whatever it is, get into the holiday spirit and cross some seasonal chores off your to-do list by turning holiday decorating into a date night with your person.
2. Binge your fave holiday movies while sipping hot chocolate
Is it really the holidays if you’re not watching Home Alone, The Grinch, or some cheesy rom-com on Lifetime? This date is perfect for a Friday night after you’ve told your friends you're “too tired to go out.” So grab your cozy blankets and fuzzy socks, and get ready to Netflix and chill.
3. Cook a romantic dinner together
Again, staying in does not have to mean Netflix and takeout. Sometimes an intimate evening with a home-cooked meal you prepare together is actually more romantic than dining out. Pick a recipe you both want to try (might we suggest one of these options?), open a bottle of wine, and channel your inner chef.
4. Do a virtual wine-tasting
In case you missed it, plenty of companies now offer virtual wine tastings you can do from the comfort of your own home. They send the wine to you, and you and your date can follow along as an expert guides you through the various selections in a usually Zoom-style seminar. What better way to spend a night in than exploring new wines together and refining your somm sensibilities?
5. Go to a Christmas tree farm
Alexa, play “Christmas Tree Farm” by Taylor Swift. But really, whether or not you actually want to perform the manual labor of cutting down a live tree, lugging it home, and setting it up when you could just order a fake from Amazon, spending a cozy day at a Christmas tree farm is an iconic holi-date. It’s outdoorsy without being too physically demanding, it’s brimming with cute selfie potential, and you can basically pretend you’re in the cheesy-yet-addictive holiday rom-com of your dreams. What more could you ask for?
6. Get thee to the theater
Can you technically see a play any time of year? Yes, of course. But is there something about “Going to the Theater” that just seems to ooze a certain wintery sophistication? Also yes. Whether it’s a Broadway show or a more intimate performance at your local theater, catching some live entertainment is a perfect way to spend a winter night out on the town.
7. Acquire a taste for jazz
If you’re down to class things up a bit this winter, nothing will make you feel more sexy and sophisticated than a jazz club date night. Just you and your boo sipping cocktails and enjoying some live tunes. Also, jazz is sexy, okay? It just is.
8. Learn to ski
If you and your person are already seasoned slope-hitters, then hello, ski trip. But if you don’t know your way around the slopes yet, why not take a lesson together? It’s a great opportunity to learn something new, get outside and make the most of the cold weather, and it comes with a built-in excuse to warm up with a steaming mug of hot chocolate afterwards. You’re welcome.
9. Revisit one of your fave summer date spots
While some of your favorite summertime haunts may be closed for the season, plenty of typically summery destinations are actually open year-round. Not to mention, a lot of them are probably less expensive and less crowded during the off-season. Plan a trip to your favorite beach town or seaside locale and see what it’s like in the winter. Chances are it’s probably a lot more peaceful.
10. Two words: spa day
What better way to unwind and beat the winter blues than a spa date? Treat yourselves to a couple’s massage, a relaxing sauna steam, and/or some beauty treatments that your dry winter skin will definitely thank you for.
11. Spend the afternoon at a cute café
Stake out the cutest, coziest coffee shop you can find (no, we’re not talking about Starbucks) and warm up with a latte (complete with cute latte art, obvs) and some sweet treats. Lots of cafés also have live music, board games, or other fun activities to enjoy together.
12. Take a mixology class
Lots of bars offer mixology classes where you and your date can not only enjoy some delicious seasonal cocktails, but also learn to make them yourselves. If you’d rather not leave the house (I hear you) there are also virtual options you can attend online from the comfort of your own home.
13. Plan a winter sex fest
If it’s too cold to get out of bed, then don’t. Take advantage of the dreary weather by planning to spend a whole day in bed together, and don’t be afraid to go all out. Try some new toys, put on your favorite lingerie (bonus points for slipping into something a little more festive), and run through as many of our winter sex positions as your horny little hearts can handle. When you’re finally all sexed-out, treat yourself to a steamy post-sex shower and some fireside cuddling.
14. Go to a bookstore
Head to your favorite independent and/or used bookstore and spend an afternoon exploring the stacks together. You can each pick out a book for each other, then post up at the nearest coffee shop or curl up by the fire and enjoy a relaxing evening catching up on some reading.
15. Take a romantic bath together
The holidays tend to be all cute and adorable, but they can also be pretty chaotic. Whether you’re wrapping things up at work or getting ready to visit the family, you deserve to relax a little bit with your partner by taking a warm bath or shower together while sipping champagne and eating some banana bread. I don't make the rules.
16. Plan an indoor picnic when you‘re snowed in
If you hate going out in the cold, why not bring the outdoors in with an adorable picnic? Make space in your living room, throw down a blanket, and spend the rest of the night eating off a charcuterie board, drinking a specialty drink, and cooking up your favorite desserts.
17. Make a gingerbread house together
Prove that you work well together by building a gingerbread house together. You don’t really have to spend too much money doing this, and you can end up eating it in the end if it falls apart.
18. Invite another couple over to your house for an indoors double date
The holidays are for spending time with your loved ones, and yes, that of course includes your sister and her partner as well. On a night when you know you won’t get snowed in, invite some friends over for a double date. Make dinner together and play some games for some well-deserved time off.
19. Make s’mores together
I know s’mores are kind of associated with summer or fall time, but TBH, having a fire pit in your backyard when it’s cold outside sounds a lot better than when it’s above 80 degrees, just saying. If you decide to go through all the trouble of making a fire pit, use the time and opportunity to make a s’more while you're at it too.
20. Paint and sip
The key to dating in the winter is you must choose activities that are either a) at home in your PJs or b) inside in a heated place. For this reason, if you want to venture out, try signing up for a paint and sip class where you bring your own wine and create your masterpiece together.
21. Play literally any type of game together
Board games, video games, horny truth or dare, you get the picture. This is quality time to a T, plus, it’s free bonding.
22. Go on a drive or walk to look at holiday lights
All you need to do is bundle up, grab a boozy hot chocolate, and make your way through the neighborhood (or down Fifth Avenue if you live in New York City). Did we mention this activity is totally free?
23. Go to the movies
I’m all for going to other buildings during the winter just to stay warm, so why not catch a newly released movie while you’re at it? You’ll get to enjoy your partner’s company while enjoying some movie snacks like popcorn, candy, and slurpees.
24. Go to your favorite restaurant
If you want to avoid massive crowds at your fave restaurant, schedule date night during the week. Not only will you have something to look forward to after school or work, but you won’t have to be rubbing elbows with other diners since it will likely be emptier than on a Friday or Saturday night.
25. Build a snowman
Okay, maybe you don't have to build a snowman, but do something together on the first day of snow. Whether it’s frolicking through the white and drifted snow, having a snowball fight, or building a snowman together, make sure to pack some warm gloves and waterproof boots.
26. Go ice skating
Take some time this holiday to hit the ice. Make it better by getting your favorite Starbucks holiday drink after.
27. Go on a winter hike
If you’d rather stay active than hibernate this season, go outside for a walk. The scenery should be absolutely breathtaking after a night of snow showers, and it’s always rewarding when you’re able to get a workout in while getting some fresh air.
28. Visit holiday shops together
There are normally tons of festive shops around in cities. But if you’d rather get a good deal, make a plan about what stores to hit during Black Friday and get up at 4 a.m. together. The couple that snags holiday deals together, stays together.
29. Explore winter villages
Many towns and cities tend to have winter villages during the season where people can buy holiday trinkets, different foods, and spend lots of time together. Get together after work and hit up a jolly wintery event instead of doing the same old bar hopping.
30. Take holiday photos together
The holidays are always so much a romantic time, so why not capture those memories by snapping some holiday pics together? Whether it’s an impromptu selfie ice-skating selfie, posing in front of a gigantic Christmas tree, or coordinating a professional holiday photo shoot and mailing out Christmas cards (if you’re Martha Stewart-level like that) take some pics for the ’gram and make a date out of it.
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