7 Ridiculously Cute Winter Date Ideas for You and Your Boo

The warm months lend themselves to all sorts of cutesy date nights. Think putt-putt golf, a midday swim, and happy hour on a rooftop bar. Winter dates, on the other hand, can feel like slim pickings. How many times can you stay in and watch a movie? (OK, so the answer may be a lot — but variety is the spice of life and arguably the key to a happy relationship.) 

The truth is that it’s always good to get creative with your winter date ideas — and not just so you have cute pics for the ‘gram. New ventures open up new parts of yourself, foster deeper bonding, channel all the romance, and honestly keep you and your partner feeling excited about each other and the world around you.

If you’re a bit in a dating rut these chilly months, we’ve got you covered with some ridiculously cute winter date ideas. Start penciling them into your calendar and get excited to make the season really count. 

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Do a quick Google search for an old school arcade, or maybe even an arcade bar, and make a whole afternoon or evening of it, suggests Tammy Shaklee, relationship expert and founder of H4M Matchmaking. She recommends having a staff member give you some helpful tips, and establishing your couple’s rules for play before diving in.

From there, select a handful of games you’ll compete against and set a price. Maybe it’s a back rub or paying for dessert later.

“Secretly take a video of your partner at the height of play and play it back to them during dessert,” Shaklee suggests. “No posting on social, but keep it private as one of your couple’s memories.”

Few things are as cozy as a crackling fire, a hot drink in your hand, and boo by your side. Add in a card game that gets you talking and you’ll have one of the best nights of your life. 

“A fireside date sets you up for an evening filled with deep meaningful conversation,” says relationship psychologist Dr. Cheryl Fraser, Ph.D. “The warmth soothes and relaxes you, and the intimacy provided by partial darkness illuminated only by flickering firelight can help you feel more bold. Quite simply, it’s easier to reveal and be vulnerable when nestled by a soothing fire in the half light.” 

To get the convo rolling as brilliantly as the fire itself, break out Where Should We Begin — A Game of Stories. It was developed by Esther Perel, a psychotherapist and leading expert on modern relationships.

Instead of a date night, consider making it a full blown date weekend by booking a nearby cozy cabin to swap the hustle and bustle for a weekend of romance.

Even if you do nothing but hang out in the cabin all weekend long, it’s the perfect way to get out of a routine and you’ll feel less likely to tackle all the to-do’s and chores in your own home. 

It can also invite you to step away from technology and spend more intimate, meaningful time with your partner. Stargaze, snuggle up by the fire, read a book, journal, bake, and play. 

Like we said above, variety is the spice of life. Too much of one thing and not enough of another might make for a boring weekend, so set out to enjoy the full spectrum with bae on your next date. 

“Find a safe but really lowbrow place to have a cheap beer and listen to the locals tell their stories from their favorite barstool. Then, contrast that experience by having a glass of champagne at the finest place you can afford in town,” suggests Shaklee. “Think the lounge at the Four Seasons or the Ritz Hotel downtown.” 

The contrast in the bartender to the fellow patrons will certainly make for great conversations and observations. 

Remember how carefree you felt as a kid on a sled? You’re all bundled up in your puffy winter apparel, mittens securely fastened, nose red and wind in your face as you zoom down a hill? Only to make it to the end giggling and ready to march on up the hill to go again? 

Capture that same feeling, but this time with your cutie pie by your side. Bundle up, grab a sled, and get ready for some good old fashioned fun. Not only is sledding a great way to fuel your adventurous side, it’s the perfect excuse to grab on tight to your bae. 

Feeling bold? Dare to do a couple’s polar bear cold plunge! There’s no doubt you’ll bond over the experience, and there’s a solid chance it’ll move your bodies closer together to find any warmth you can! (Do keep safety at the forefront of your mind. Some venues and resorts provide various controlled water temperatures for this experience.) 

“After, wrap each other in cushy robes and hug it out, take a hot bath, shower or jacuzzi together, and then maybe take it to the sheets,” says Dr. Fraser. “You get a natural high and even a libido boost caused by an increase in adrenaline, endorphins, and the sex hormones testosterone and estrogen.”

She suggests taking some silly “before and after” selfies to prove you were crazy enough to do this!

If you’re in the midst of enjoying the holidays, lean into the Christmas vibes by putting on a holiday playlist, building a gingerbread house, and then heading out afterward to check out the local lights. 

While building a gingerbread house, you’ll be able to see just how creative you and your partner can get — plus you’ll get a better sense of their personality. Opt for a fun theme, like your dream home, dinosaurs, winter wonderland, or retro. Not only does this require great teamwork skills, it’s a fun way to get creative in the kitchen. 

After all your hard work, grab some mulled apple cider or a cup of hot cocoa and bundle up for a romantic stroll through your city’s best winter light installation.