Holiday First Date Ideas for a Winter to Remember

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‘Tis the season to be festive and add some sparkle to your romantic life. Forget about spending all your time inside the house or with relatives that you haven’t seen since last year. The holidays are the best time to meet someone new, and WYP has some holiday first date ideas to help you celebrate!

If you’re feeling the cheer, it’s time to find a special someone who enjoys the spirit of the season as much as you do. But you’ll need some inspiration! Here are our favorite ways to mix it up with a first date this time of year.

Outdoor Holiday First Date Ideas

Outdoor romance is always refreshing, especially in the wintertime! These are some great ways to break the ice on a first date:

Ice Skating

If you’re looking for the most romantic winter first date, ice skating is the classic way to go. It’s a guaranteed good time when you can glide across the ice as you get to know someone new. When you get chilly, just grab a cup of hot chocolate and spend some time enjoying each other’s company.

Build a Snowman

Are you and your date feeling playful? This is one of the best holiday first date ideas to make you feel like a kid again. Get out there and build a snowman! It’s such a fun way to feel like a kid again while you work together and make easy conversation. And if it ends up in an impromptu snowball fight, even better! Just be sure to grab a warm drink or meal afterwards.

Shred the Slopes

When winter brings out the athlete in you, grab your gear and hit the mountain with your date! Whether you’ve got the best snowboarding moves or stick to the bunny slope, it’s always a good time when you stay active and cheer each other on. Plus, ski resorts have the best restaurants where you can hang out once you’re done shredding.

Take a Snow Hike

Outdoor enthusiasts can’t get enough of snow hikes in the wintertime. They’re a magical experience that you and your date will always remember. And you don’t need to be pro hikers. All you need are some good boots and cozy clothes to enjoy this holiday first date idea. For an extra special date, pack a light lunch and hot beverage to share once you reach the top of the mountain.

Go to an Ice Hockey Game

Just because you’re not feeling sporty it doesn’t mean that you and your date can’t enjoy winter sports. Ice hockey games are super fast paced and exciting to watch. Nothing like cheering for a team to bond with a new friend. Plus, who doesn’t love stadium snacks?!

Indoor Holiday First Date Ideas

Watching the snow by the fireplace is better with a special someone by your side. Cozy indoor dates are the definition of winter romance, and these are our top picks:

Catch a Local Play

Ready for a break from the holiday parties? Find a date and check out the local art scene at a nearby playhouse. It’s a great way to support your community and get into the holiday spirit. After the play, you can grab a bite for a chance to chat it up and get to know each other better.

Mulled Wine Tasting

Wine tasting might be a great warm weather date, but have you been mulled wine tasting? This holiday first date idea is guaranteed to help you and your date get toasty with a yummy treat that’s perfect for a cold night. If you don’t have a mulled wine tasting spot nearby, just look up a few recipes and make your own for an unforgettable at-home first date.

Make Fondue

Want a date idea that’ll melt your heart? Try a fondue restaurant! Whether you’re into cheese, chocolate, or both this one’s a definite crowd-pleaser. It’ll make you feel like you took a trip to Paris without leaving town.

Have an Indoor Picnic

If you’re missing the summertime, you and your date can pretend it’s July with a cute indoor picnic for two. For extra fun you can even set up a plaid tablecloth, add flowers, and a wicker basket.

Holiday First Date Ideas Full of Fun

Everyone feels a little more playful during the holiday season. If you want to infuse your date with some of that jolly spirit, these are some fun ways to do it:

Go Ugly Sweater Shopping

Holiday sweaters aren’t just for great aunts anymore. They’re all the rage at office parties, friends gatherings, and even first dates! If you and your partner don’t own one, hit the shops to find the ugliest sweater and then walk around town to show them off. If you find a cozy cafe or decorated restaurant, hop in for yummy food and good conversation.

Visit a Street Festival

Street festivals are a blast any time of year, and wintertime is not the exception. They’re filled with kick knacks and delicious snacks that make them a dreamy spot for a first date. With so much to discover, you and your partner can spend hours wandering around these winter wonderlands. 

Go to the Drive In

For a fun holiday first date idea that’s an alternative to the movie theater, check out your local drive in. These retro spots are a cool way to catch a classic holiday film with a first date. They’re usually decorated extra cute for the winter season, with plenty of Insta-worthy backgrounds for you and your date to strike a pose.

Hit the Arcades

Remember when you were a kid and spent snow days at the arcade? First dates are the perfect chance to relive those days! No need to deal with real winter weather when you can hop on the arcade snowmobile and laugh the afternoon away with a fun date.


No matter what you and your date decide to do, you’re sure to have a wonderful time when you embrace the spirit of the season. So go ahead and ask someone out today. Kickstart that winter romance with our holiday first date ideas!


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