10 Winter Date Ideas

Potential beau not included.

The holiday season is one of the most romantic and enchanting times of the year; what’s a better backdrop for a new romance than the crackling of a fireplace, sparkling snow and the fresh scent of pine? Whether you’re meeting your potential new boo for the first time or planning a date night with your long-term partner(s), use our festive winter date ideas all cuffing season long to get yourself onto your date’s ‘nice’ list.

Hit up a festive outdoor skating rink

There’s nothing more joyful than an ice skating date in the winter — it’s a great opportunity to hold hands with your date while you glide over the ice, twirling to quintessential holiday tunes.

Have a ball together with midnight bowling

If you’re not the type to wander through winter streets on a snowy day, head to your nearest bowling alley — or show up after midnight for disco and neon lights. Bowling is a cheap, easy and classic activity you can use to bond with your date or turn up the competition between you. Don’t forget to grab a pair of Molson Canadians at the alley bar for a fun night of casual drinks and plenty of laughs.

Peruse through art at a museum

Into first dates filled with thoughtful conversation? An art or historical museum is the perfect way to generate an intellectual spark with your date. It’s also a useful tool that can provide you with insight on each other’s interests — and whether you vibe with each other.

Host your own bake-off together

A holiday-themed bake-off is every die-hard foodie’s dream first date. Pick a festive dessert category — like gingerbread cookies, snickerdoodles or cinnamon rolls — and let the best baker win.

Explore a magical holiday market

Dial up the holiday magic on your winter date night by browsing the artisanal wares of an annual holiday market. With so many priceless selfie opportunities and the market’s cheerful, festive ambience, it’s the perfect location to make a memorable first move on your date.

Plan your own café crawl together

Turn your first date into a day of cozy exploration with your very own café crawl itinerary. Stake out the best little-known coffee shops in your area and spend a sweet day hitting your itinerary goals with your bae.

Spend a night crafting your own homemade pizza

The ultimate bonding experience that’s perfect for a snow day — a homemade pizza date. Pizzas tend to be time-consuming to create from scratch, giving you plenty of time for epic conversations and getting to know your date. Plus, you’ll get to discover whether they’re obsessed with a pizza topping you absolutely hate.

Fight through an escape room together

Hear us out; an escape room may not be the most traditional of winter dates, but it’s the best way to find out if you and your date can work together during times of crisis. Whether you escape frustrated and turned off or even more into your date, you’re in for a memorable night together.

Hunt for pre-owned gems in thrift stores

Spending a day digging through piles of potential gems with your date is a great way to figure out their personal style and taste — and whether they make a great thrifting wingperson. Raise your chances of finding a rare piece by hitting up a variety of pre-owned stores for best results.

Plan your future together at IKEA

Snowed in? IKEA is the optimal location for a low-key first date with your boo. Not only can you grab lunch and a few must-haves for yourself, but you can also discover your date’s taste in interior decorating — and whether that jives with your fantasy dream home.

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