Holiday Date Ideas

As the streets begin to sparkle with festive lights this winter, there's undeniably romance in the air. The holiday season brings with it a unique magic—it’s a time of joy, warmth, and togetherness. People are up for having fun and celebrating the year gone by, as well as looking forward to new adventures in the year to come.

Most of us get some days off work to enjoy (yay!), so it's really no wonder that the holiday season is a prime time for dating. There are countless cute, fun, and romantic activities to do at this time of year, all of which are better with a date. So throw on your ugliest Christmas sweater and hit the festive dating scene! 

First up, why not plan a romantic evening stroll through a local park or botanical garden adorned with twinkling lights? Many cities also host special light festivals during this time, which give you the perfect backdrop for a magical date night, and some cute couple selfies along the way.

If you’re more into being warm and cozy in the evenings, than shivering on a romantic walk—we’ve got you covered. Whether it's at a rustic cabin, a local coffee shop, or your own living room, there's something inherently romantic about a fireside chat. Snuggle up with your date by the fireplace, sip on hot cocoa or mulled wine, and let the crackling flames create a warm and intimate vibe.

If you’re comfortable inviting a date over to your place (because let’s face it, not having to worry about how you’re getting home is very appealing at this time of year), how about suggesting a holiday movie night? Create a mini movie marathon featuring your favorite holiday films. Whether it's a classic or a heartwarming rom com, getting cozy under a blanket with drinks and snacks will no doubt turn up the thermostat on your relationship.

Our last holiday date night idea involves leaving the house (sorry!) but trust us, it’s going to be a blast. Lace up your skates and hit the ice hand in hand. Many cities set up outdoor ice rinks during the holiday season, and they’re often open late into the evening. There’s no better way to get to know a date than watch them flailing around, stumbling and careering into the sides of an ice rink. Once you find your flow, you’ll be gliding in effortless circles and feeling like you’re in your very own holiday movie.

Let’s start by getting creative in the kitchen. If you’re really looking for a cute holiday date idea, hosting a cookie decorating party is *chef’s kiss*. Roll up your sleeves, whip up a batch of sugar cookies, and let the decorating fun begin. From festive sprinkles to colorful icing, you and your date can express your personalities through your designs and enjoy the tantalizing aroma as they bake.

For something a little more challenging, channel your inner architects and embark on a gingerbread house decorating adventure. Whether you opt for a DIY kit or bake from scratch (impressive), building and decorating a gingerbread house together will get you in the mood for the winter holidays. If you work well together and are still friends at the end of the experience, it bodes very well for the future of your relationship!

Another cute date idea at this time of year is to explore some local holiday markets. Savor the sights, sounds, and scents of the season as you peruse stalls filled with handmade crafts, sweet treats, and unique gifts. It's a delightful way to discover new treasures while sharing the joy of the holidays. You could even buy each other a small trinket as a souvenir. 

Now this next cute holiday date idea might not be possible for everyone. Why? Because it involves there being real snow to play with. If you're fortunate enough to have a snowy setting, embrace it with a snowman-building contest. Get in touch with your inner child, roll up snowballs, and see who can create the most impressive snowman. Bonus points for adding quirky accessories!

If you’re all about having fun and not taking dating too seriously, then we have got some whacky date ideas for you. First up, embrace the seasonal tradition of the ugly sweater with a themed bar crawl. Find the tackiest sweaters you can and hop from one festively decorated bar to another— just don’t expect to be let into anywhere with a dress code!

Next up—something that involves quite a bit of pre-planning but could result in a memorable festive date—a holiday-themed scavenger hunt. Craft a list of festive items or clues that lead to holiday-themed locations (a beautifully decorated Christmas tree in a town square, a cute gift shop, a synagogue or church for example). Not only will you have shown how thoughtful and fun you are, but you’ll have set the benchmark pretty high for when it’s their turn to plan the date.

If you're in an area with access to snowy landscapes (lucky you) then booking a sleigh ride for two is a whimsical and romantic date idea that’s guaranteed to lead to some seasonal snuggles. Get cozy under a blanket, breathe in the crisp winter air, and enjoy the scenic beauty as you glide through the snow. 

If, like most of us, you’re lacking a dusting of perfect white snow to get you in the festive spirit then try this fun holiday date idea instead: Tap into your creative side with a DIY craft night. From making personalized ornaments to creating your own holiday decorations, this date idea allows you to express your individuality while creating something special together.

We’re feeling gorgeous, glamorous, and ready to revel in the joy of the season—so why not host a holiday-themed cocktail (or mocktail) party for two? Experiment with creating seasonal drinks like eggnog or cranberry mimosas, and don't forget to add a dash of personality with fun garnishes and colorful glassware. You could suggest you both dress up in black tie or your fanciest holiday party outfit to really up the ante, but more important than how you look, is how you feel. This party date idea should be comfortable, fun and intimate—a great way to enjoy each other's company while sipping on delicious drinks.

Not everyone gets to be together over the holidays, but don’t let that stop the party. If distance keeps you apart during the holidays, organize a virtual game night. Play festive online games, quiz each other on holiday trivia, or play virtual board games. It's a playful and interactive way to connect and share a laugh, even if you're miles away.

If you are lucky enough to have time together IRL for a holiday date party, a nice idea is to transform your dining area into a magical wonderland with twinkling lights, candles, and holiday decor (maybe that you’ve made yourself—see above). You could cook a special holiday meal together or order from your favorite restaurant. 

Slightly less fancy, but more likely to get you in the party mood, is a holiday-themed karaoke night for just the two of you. Pick your favorite festive tunes, create a playlist, and take turns belting out your best renditions of classic songs. If you can feel bold enough to lose your inhibitions and sing to each other, it’s a great sign of compatibility.

The holidays offer a unique canvas for dating adventures. Whether you're sipping hot cocoa by the fireplace, embarking on a festive scavenger hunt, or building snowmen together, these holiday date ideas are designed to infuse your season with warmth, laughter, and a dash of romance. Happy holidays!