10 Cute Holiday Date Ideas To Try With Your Boo

Turn your life into a Hallmark movie.

An expert shares her top recommended holiday date ideas.
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It’s the perfect time of year to enjoy all the festive activities — cheesy ones included — with the people you love. If you’re in a relationship or seeing someone new, there are a plethora of cheery and cute holiday date ideas that you and your boo can enjoy. Whether you’re looking to be extra and plan a day full of romantic activities worthy of a Hallmark movie or to check out something more relaxed and subtle, the possibilities truly run the gamut.

“With the cheer in the air, you can find many things to do to enjoy the holiday season with someone you just started crushing on or someone you’ve been dating for a while,” says professional matchmaker and dating coach Anika Walker. There’s an option for every kind of activity you might be in the mood for: You can bundle up with your honey and hit the streets, book a very Christmas-sy ice skating date, or plan a warm and cozy night at home with cocoa and holiday movies. Whatever you and your S.O. go with, now happens to be an extra merry time for you to create memories together while making the most out of the season.

Read on for 10 expert-approved cute holiday date ideas to try before the new year comes around.


Grab Hot Chocolate

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You can’t go wrong with a classic holiday date night option like grabbing hot cocoa when it’s chilly out, and Walker says it’s particularly great for a new boo. “It’s low pressure and creates the space to chat and get to know each other in a cute, casual way,” she says. And if you’re feeling adventurous: “Make it interesting and do a hot cocoa crawl!” You can bundle up, grab a cup from a local coffee shop and take a cozy walk together, or even make your own loaded hot chocolate for an at-home date night.


Attend A Tree Lighting

Catching a local tree lighting can really amp up your holiday cheer. Walker also says this kind of event can be a great place to introduce your new partner to friends for the first time in a group outing. “Tree lightings are usually very festive and calming, allowing for a casual meetup surrounded by an experience,” she says.


Hit Up A Holiday Market

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For some Hallmark Christmas movie vibes, look no further than a holiday market. With the bounty of decor, vendors, food, and oftentimes festive activities you can try, these shops can be an exciting way to enjoy the season with your partner. “Whether you are buying something for your date or just walking around through the sea of holiday cheer, this activity is sure to be a hit,” Walker says.


Visit A Holiday-Themed Restaurant

Going out for dinner and drinks is a classic option for date night, but Walker notes that the holiday season offers a fun twist on the activity. “Try looking for holiday-themed restaurants or bars that offer festive menus,” she says, pointing to restaurants like Serendipity in New York City. Do some digging to find the cutest hot spots in your area.


Check Out Holiday Lights

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As a fan-favorite date option this time of year, Walker recommends walking or driving through local neighborhoods that are full of extravagant Christmas light displays or even botanical gardens that are decked out for the occasion. You can pack up some hot cocoa and cookies to keep the festive spirit strong.


Try A Holiday DIY Home Activity

If you’re into all things DIY or handmade, Walker recommends creating some festive art or decorations together for a fun date night at home. “Try doing some DIY activities such as making a Gingerbread house, stockings, or ornaments,” she shares. “This is a cute date and a fun, low-key way to stay in while enjoying the holiday spirit.”


Go Ice Skating

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Ice skating is another top-notch holiday date idea, and one that happens to be more active. “A date where you are doing an activity is always a plus, as it allows you to create memories and experience your date in a different enjoyable way other than simply sitting across the table having dinner and drinks,” says Walker. Even if you both have two left feet, hanging onto each other and taking a few tumbles on the ice can be something you laugh about later.


Get Tickets To A Holiday Show Or Concert

Is there a local screening of It’s A Wonderful Life happening soon or a caroling concert at a nearby music venue? Add in some drinks or a meal beforehand, and you’ve got yourself a full and festive date night. “Seeing some classic holiday shows are always a perfect date idea that can be planned out in advance and something that you can experience with a larger group of people as well,” says Walker.


Volunteer Together

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Walker also encourages you to try something different by finding volunteer opportunities in your area. “Giving back to the community is great year-round, but extra special if you can find some time to do it around the holidays,” she says. Bonus points if either of you have an acts of service love language.


Host A Holiday Game Night

If you and your partner have a space you can share with others, consider hosting a holiday-themed game night. “Invite other friends or couples over and bring in the holiday season with a group date night,” Walker says. Participating in activities with other couples can be a great way to bond, and it might even lead to more exciting double dates in the future.


Anika Walker, professional matchmaker and dating coach