30 Holiday Date Ideas To Try With Boo this Season

Ah! the holiday season that magical time of year when the air smells like cinnamon, everyone’s rocking cozy Christmas sweaters, and your calendar is somehow fuller than Santa’s gift bag. But pause for a second, babe, and remember: this season is also about connection, love, and making memories with the people who mean the most to you.

The holidays are basically the ultimate backdrop for romance. Hellloooo have you seen a Hallmark movie? It’s the perfect time to slow down and show your partner just how much you care. 

So, with all that holiday magic swirling around, why not add a little extra sparkle to your love life? Today, we’re sharing a festive roundup of holiday date ideas that’ll make this season one to remember. But, before you go on that date, get in the Christmas spirit with this nostalgic episode of Twenty Whatever ALL about our fave parts of the season. Who knows, it may inspire you’re next date!

Now, grab your boo, and let’s make this season unforgettable!

30 Holiday Date Ideas To Try This Season

1. Go ice skating.

One thing that screams “ultimate holiday spirit” is gliding (or, let’s be real, clinging) around a sparkling skating rink. Ice skating is one of those classic winter date ideas that just hit differently. It’s playful, romantic, and totally Instagram-worthy. Plus, falling on your butt is a prime opportunity for some cute laughs and maybe even a rescue kiss.

2. Decorate a gingerbread house together.

Is decorating a gingerbread house messy? Absolutely. But is it also ridiculously fun and a total relationship-bonding moment? You bet your candy canes it is!

Will your gingerbread creation look like a Pinterest masterpiece? Probably not. But that’s the beauty of it. You’ll get to laugh together when your candy roof slides off, or one of you eats more decorations than you actually use.

3. Bake and decorate holiday cookies.

Here’s how this will most likely go down: You and your boo throw on an apron, blast some Mariah Carey, and channel your inner pastry chefs. Roll out the dough, break out the cookie cutters, and get ready to create some edible masterpieces (or hilarious monstrosities).

You can both get competitive about who can make the best snowman cookie or collaborate on a gingerbread reindeer that’s almost too cute to eat. Almost. 

4. Wrap presents.

Who says wrapping presents has to be a solo chore? Turn it into a flirty, festive holiday date night and let the gift-giving magic work double duty. Start by dividing and conquering; one person can cut the paper while the other masters their bow-tying. 

But let’s not pretend it’s all smooth sailing. There will be rogue pieces of tape sticking to places they shouldn’t, and that one oddly shaped present that defies every wrapping technique known to mankind. But hey, those little hiccups just make the experience even better. When the gifts are all wrapped and look like they belong under the fanciest Christmas tree, you’ll feel accomplished and extra connected.

5. Share hot chocolate and stargaze.

This is the kind of holiday date that’s just magical. No frills, no fuss, just you, your boo, and the universe showing off its best light show. It’s practically romance 101. 

Grab your favorite blankets, make sure your mugs are filled to the brim with hot cocoa (maybe even top it with whipped cream or marshmallows), and find a cozy spot outside. But, this isn’t just about staring at the stars (though that’s amazing, too). It’s about the connection. You can talk about everything under the stars. And, that’s what makes it truly magical.

6. Wear matching Christmas sweaters and take selfies.

The holidays are the perfect excuse to go all out with the cute and cheesy stuff. And, what’s cuter (or cheesier) than rocking matching Christmas sweaters with your boo and taking some hilarious selfies together? 

You know what they say: couples that wear ridiculous holiday gear together stay together. Or something like that. Trust us, your future kids will thank you when they look back at these iconic pics.

7. Take a sleigh or carriage ride in the snow.

Snowflakes falling, cozy blankets, and the sound of jingling bells. Does it get any more holiday-movie magic than a sleigh or carriage ride through the winter wonderland? This is one romantic Christmas date idea that’ll make you feel like you’re starring in your very own Hallmark movie. You can get your sleigh ride in a park or hop into a horse-drawn carriage. 

8. Go skiing or snowboarding.

If you and your partner are ready to swap the cozy indoor vibes for some heart-racing, snow-covered action, this is the holiday date idea that’ll give you both a major thrill. Get ready to trade in your mugs of hot chocolate for snowball fights, epic runs down the mountain, and some serious laughs.

9. Pick out a Christmas tree at a local farm.

There’s just something so magical about strolling hand-in-hand through rows and rows of fluffy, fragrant trees, trying to decide which one will look absolutely stunning in your living room. But the best part is decorating that tree when you get home! Besides, is it really the holidays if you don’t have a cute little Christmas tree to decorate together? 

10. Attend a holiday play or concert.

This one is for all you culture lovers and Christmas enthusiasts out there. Is there anything more enchanting than cozying up next to your person in a beautifully decorated theater and getting swept up in the captivating sounds of a live Christmas concert? I think not! 

Whether it’s a classic rendition of “The Nutcracker,” a soulful holiday concert, or a hilarious comedy show, it’s the perfect opportunity to dress up in your prettiest holiday attire and feel like a total VIP. 

11. Shop at a holiday market and pick gifts for each other.

We don’t know about you, but we love supporting small businesses. And you can show off your thoughtfulness by finding those treasures you know your partner will adore from stalls at the holiday market. Plus, the holiday season is all about giving. So what better way to show your love than by putting in the extra effort to find them something super special?

You get to pick out gifts for each other on the spot! It’s like Secret Santa, but you already know your “Santa” is fine. You could even turn it into a little friendly competition. Set a budget and see who can find the most creative gift. The winner gets an extra marshmallow in their cocoa. Or, better yet, a smooch under the mistletoe. 

12. Volunteer together at a charity event.

Volunteering together is not only an amazing way to spend the day, but it’s heartwarming and rewarding. You can agree with us that it can be extra sexy having a partner who cares. Plus, volunteering together gives major couple goals and makes you both feel like holiday superheroes.

The look of pure elation on the faces of those you’re helping can instantly put you in the holiday spirit. And let’s not forget about the sense of fulfillment you’ll both feel. This date idea is the perfect way to remind yourselves of what the season of giving is all about.

13. Create a holiday scavenger hunt.

This idea is the perfect way to inject a little playful competition into your festive season while spending quality time with your boo. It’s cute, creative, and customizable.

You both can come up with a list of holiday-themed items to find, or a series of tasks to complete to find each other’s Christmas presents as the grand prize. You’d have so much fun that you’ll want to consider adding to your list of date night jar ideas because it’s the kind of thing you’ll want to repeat every season. 

14. Plan a holiday photoshoot.

Saying “cheese” might look cheesy (yes, we know what we did there). But, it’s the perfect opportunity to dress up, get creative, and capture all those precious moments you can look back on. Talk about a gift that keeps on giving. It’s also the perfect excuse to show off those matching Christmas sweaters. (Don’t lie, you know you love them.)

Start by picking your theme. Are you going for cozy by the Christmas tree, glam in front of glittering Christmas lights, or a playful outdoor shoot in the snow? Then, pick your location and props, if needed. You can get as creative and spirited as you want. 

15. Make a time capsule of holiday memories.

A time capsule is the ultimate keepsake. Think of it as your love letter to your future selves because you’ll want to relive these cozy moments repeatedly.

All you need to do is grab something sturdy to hold your memories a jar, box, or even an old tin. Next, gather all the little things that made this holiday season extra magical: a Polaroid from picking out your Christmas tree, ticket stubs from that holiday play or concert, or even a sprig of mistletoe.Take inspiration from your annual holiday traditions! 

Then, add some personality! Write love notes or jot down your favorite memories from this fun Christmas. And when it’s full, seal it up and mark a date to open it. Whatever timeline you pick, this little time capsule will become a treasure chest of holiday magic.

16. DIY ornaments for your Christmas tree.

Bring out the glitter because it’s time to get crafty! Working together to create personalized decorations for your Christmas tree is a recipe for some serious bonding and holiday cheer. You get to unleash your creativity as you make everything from glittery pinecone ornaments to custom photo baubles, all while making your home look extra magical.

17. Roast marshmallows over a backyard fire pit.

Who says you need a big cabin in the mountains to live your best cozy life? A backyard fire pit is all you need to turn up the heat on your Christmas date night. 

Grab some blankets, bundle up in your cutest sweaters, and light up that fire pit. (If you don’t have one, no worries. A mini tabletop fire bowl works just as well!) Load up on all the goodies: marshmallows, graham crackers, chocolate, and even peppermint sticks for a festive twist. And you’re all set for a nostalgic and romantic date! 

18. Decorate your home with Christmas decor!

It might seem too stressful to be considered a date, but if you do it right, decorating your home together can be a fun bonding activity for you and boo. Besides, this is the perfect time to put those DIY Christmas decorations to good use. Then, channel your inner interior designer and create a space that’ll serve major holiday vibes. 

19. Sample festive foods at a fun Christmas market.

These markets are the place to soak up that holiday spirit and treat your taste buds to all the festive deliciousness they deserve. Make it a date by going to your local Christmas market to sniff out the churros, roasted chestnuts, or gingerbread. Because when else is it socially acceptable to eat dessert first? 

Sampling festive foods at a Christmas market is more than just eating. You get to explore together, giggle over messy bites, and create memories you can both look back on and say, “Remember when we tried that reindeer-shaped cookie?”

20. Play in the snow.

Channel your inner kid by playing in the snow with your boo. You don’t even have to plan a date to do this. It could be totally random and spontaneous.

Whether you’re building snowmen, starting a friendly snowball fight, or perfecting your snow angel skills, this date idea is pure, unfiltered fun. You might get a little cold, but it’ll all be worth it after you’ve laughed your heart out. By the time you’re done, you’ll have rosy cheeks, cold hands, and warm hearts.

21. Organize a holiday trivia night.

Time to put your holiday knowledge to the test and see who’s the true queen (or king) of Christmas! Organizing a holiday trivia night is a fun way to bond with your boo. It’s also the perfect chance to flex those random facts you’ve picked up from your favorite holiday movie marathons over the past few years. 

Now comes the fun part, where you get creative with your questions. Include categories like favorite Christmas traditions, classic carols, and those cringy yet iconic Hallmark movie plots. And, don’t be afraid to throw in wildcard questions. 

22. Sing some Christmas karaoke.

Forget about those quiet nights by the fire. This idea requires you to get loud and have a blast. Christmas karaoke is a great way to let loose and share a ton of laughs. You can even throw in some festive costumes or holiday props to take your performance to the next level. If you’re doing it right, there should be lots of playful banter, friendly competition, and, of course, a ridiculous amount of laughter. 

23. Go caroling or attend a sing-along.

Warm up those vocal cords because this holiday date idea is for hitting the high notes. If caroling is your thing, gather a group of friends to do it with or do a duet with your partner.

Not a natural-born singer? Don’t sweat it. This date idea is about the fun, not the pitch-perfect performance. Laughing through the missed notes and over-the-top “12 Days of Christmas” choreography is half the magic.

If you’re going caroling, don’t forget to grab your warmest “Happy” sweatshirt and pants with a thermos of hot cocoa and a solid setlist. (Don’t skip the classics. Everyone loves a good “Jingle Bells” rendition)

You can find a neighborhood glowing with Christmas decorations to set the perfect backdrop for your duet. Or, if you’re more of a crowd-loving couple, head to a community sing-along where you can channel your inner rock stars.

24. Attend a tree-lighting ceremony.

A tree-lighting ceremony is the perfect romantic date because you’re surrounded by a crowd, wrapped up, and waiting for that moment when the lights flicker on, and the whole place glows like a winter wonderland. And that magical countdown to the big moment when the tree lights up and everyone cheers. Seriously, does it get more romantic than this?

Ensure you arrive early to snag the best spot, and let the magic happen. Whether you’re watching the lights dance on a giant spruce or just soaking up the crowd’s energy, this is a Christmas date night to remember.

25. Celebrate New Year’s Eve at a countdown event.

There’s no better way to ring in the new year than at a countdown event with your boo. The clock strikes midnight, and suddenly, it’s a whole new year filled with endless possibilities. This isn’t just a random date. It’s the grand finale of the holiday season and (of course) that magical midnight kiss.

It’s also a great chance to reflect on the year you’ve had and set resolutions together. On the way home, you can even tune into the episode of What We Said called New Year’s Resolutions and How to Keep Them. (For all you romantics, this is where you remind your partner how amazing they’ve made your year.)

26. Take a winter hike and enjoy snowy views.

If you’re looking for a holiday date that’s as refreshing as it is romantic, why not take a winter hike and soak in those breathtaking snowy views? The beauty of a winter hike is that it’s the perfect mix of adventure, relaxation, and romance.

Whether you’re trekking through snow-covered forests, exploring snowy mountain trails, or simply walking through a charming winter park, the holiday season makes everything look extra stunning. Take a few cute pics with your partner while you try to keep your balance because we all know how slippery those icy patches can be. Just make sure you bring the cute boots.

27. Cozy up by the fireplace reading holiday books.

If you’re in for some serious cuddling, then get cozy with boo by the fireplace and read holiday books together. You and your partner can be snuggled up on the couch, wrapped in soft blankets, a crackling fire in the background, and a stack of holiday books waiting to be devoured together. Could it get any cozier? (If you don’t know what to read, jump into The Readheads Book Club!) 

28. Write yourselves Christmas love letters.

Writing Christmas love letters to each other is your chance to channel your inner poet, let the holiday spirit work its magic, and show your partner just how much they mean to you in writing. 

Write about your favorite memories from the past year, why they’re the mistletoe to your Christmas, or how they make you feel like the luckiest snowflake in the storm.

There’s nothing too sappy. After you’re both done spilling your hearts out on these Happy Holidays Honey greeting cards, exchange letters and read them to each other. Then, watch all the waterworks flow.

29. Have a winter picnic with blankets and festive treats.

Who says picnics are just for summer? Swap out the sunshine for snowflakes, and you’ve got yourself a winter wonderland picnic that’s as cozy as it is romantic. Picture you and your boo snuggled up in blankets, surrounded by nature, and enjoying all the holiday goodies your heart desires. We’re OBSESSED!

But of course, you’ll first have to find the perfect spot and pack a basket full of festive treats. Layer on all the blankets and cushions to ensure you’re comfortable. And voila! You’ve got a sweet, intimate date that’s ridiculously easy to plan.

30. Share a kiss under the mistletoe.

What’s a list of holiday date ideas without the most obvious one of sharing a kiss under the mistletoe? You can snag a mistletoe from a holiday market or, if you’re feeling crafty, grab some green felt and make your own. 

Hang it in the cutest spot, like over a doorway, near your holiday decor, or smack in the middle of your living room. It’s the perfect excuse to pause, look at your partner, and say “I love you” without exactly saying it (like Ashley discussed in this episode of Trying Not to Care) while sharing a big kiss. 

How To Plan A Date During The Holidays

Step One: Choose a theme or activity.

Picking a theme or activity for your holiday hangout makes everything better. It also shows that you put a lot of thought into it. Themes make planning a date feel effortless. No awkward pauses, just pure fun and things you both love. 

Step Two: Set a budget.

While you might want to enjoy the season with your boo, it’s also about staying smart (and stress-free) with your spending. A budget helps you focus on what really matters, which is creating memories that last way longer than that fancy cocktail you might’ve splurged on. 

Besides, a low budget doesn’t mean low effort. Some of the most creative date ideas are actually super budget-friendly. 

Step Three: Pick the perfect time and location.

Between holiday parties, last-minute shopping, and wrapping gifts, your calendar is basically a festive battlefield during the festive season. So, you have to pick a time and location for your date that works for both of you. If you’re planning to do some activities outdoors, we suggest picking a time when it’s less crowded. If it’s indoors, all you have to do is agree on a time when you’ll both be free. 

Step Four: Capture the memories.

Are you even doing it right if you’re not taking the cutest pics or saving sweet souvenirs during your holiday date? Just take as many pictures as possible!

If you don’t want to use your phone, polaroids are making a major comeback. They make everything feel so aesthetic, and they’re perfect for adding to your fridge or a holiday scrapbook.

Slay the holidays, one date at a time.

The holidays can be a whirlwind, but it’s important to slow down and soak up those moments that make your heart happy. And, remember that it’s not about what you’re doing but who you’re doing it with. So laugh until your sides hurt, hold hands under the Christmas lights, and feel all the feelings while you watch your favorite holiday movie for the 100th time.

Want even more inspo to slay your holiday season? Our Dear Media blog is packed with ideas, tips, and tricks to keep you thriving in all areas of life, not just love. And, don’t forget to check out our jaw-dropping lineup of podcasts!