The Perfect Winter Date Ideas For a First (or 100th) Date

10 cute — and COVID-safe — winter date ideas to keep the romance alive this holiday season.

SEO: TK Winter Date Ideas to Try With Your Significant Other in 2020
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Holidays are such a romantic time — there's the glistening snow, the scent of pine trees in the air, sitting by the fire, and lots of mistletoe to go around. But this year, the holidays look a little bit different, so brainstorming cute winter date ideas is much harder because, well frankly, there's a lot less to do.

But just because 2020 sucks doesn't mean your dating life has to, so we've come up with some festive winter date ideas to keep you warm and fuzzy the whole month of December. Whether you and your long-term significant other need to spice it up for the holidays or you're going on your first date, we've got you covered with COVID-safe winter activities that will be sure to land you on the "nice" list (and maybe even the "naughty").

Outdoor Theater

Some big cities like New York and Los Angeles are now offering outdoor comedy shows to keep you (safely) laughing through this weird and uncertain time. Laughter and comedy always bring people together. Plus, it can also be a really great first date — you don't have to do much conversing and you learn very quickly if they have an annoying laugh. Win, win!

Rock Climbing

Take your love to new heights with an indoor rock climbing wall. Most gyms have reopened with new COVID-19 safety protocols that require masks, temperature checks, and hourly disinfection of surfaces. The perfect bonding experience to give you and your S.O. the skills to always make it through the rocky patches (get it?).


This one requires some snow, but definitely makes for a fun winter daytime activity. Bundle up with your plus one for a thrilling ride. Nothing brings you closer than sharing a small sled and some adrenaline.


A sweet and safe way to enjoy the winter scenery while munching on some snacks, like cheese and crackers, and sipping on some hot cocoa (or wine, tbh). Dress in layers and bring a blanket, so you can snuggle up next to your date to stay warm.

Ice Skating

There's nothing more romantic than holding hands with your boo while skating around a giant Christmas tree to the tune of holiday jingles. Grab some hot cocoa to keep you warm — and maybe spike it with some Bailey's to make the date extra fun. (But please skate responsibly!) If you find yourself in New York City this holiday season, The Rink at Rockefeller is open to book skating sessions in front of the country's most iconic tree.

Light Displays

Whether you attend an outdoor light show or just wander through your city or neighborhood to check out decorations, there's something about the twinkling lights that just sets the mood. LuminoCity Festival in New York is open this year and abiding by COVID-19 safety protocols. Check out their festive light displays with a backdrop of the beautiful New York City skyline.


Grab your gloves and boots, we're going hiking. If you and your date are thrill-seeking, outdoor adventurers, hiking through the winter wonderland guarantees lots of romance. Dress warmly!

Board Games

Opt for some childhood nostalgia with your favorite throwback board game for a cozy night in. Add a bottle of wine and call a few other couples to make this game night a bit more interesting. Our favorites are The Game of Life ($20; and Monopoly ($20;

S’mores By the Fire

When the weather outside is frightful, but the fire is so delightful… cuddle up by the fire and roast some s'mores (or chestnuts if you so desire). Get creative and mix up the classic s'mores with some new, unexpected recipes.

Take an Online Cooking Class

A cooking class is a great idea for a date — whether it's your first or 100th. It allows you to see what kitchen skills your crush possesses, which is obviously a very important quality.

Although COVID has thrown a wrench into in-person classes, many places, like Sur la Table, are offering virtual classes. So you and your date can get flirty and romantically sneak each other bites in the comfort of your own home.

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