Winter Wonderland Date Ideas

By Lana Schwartz

Winter is here and what does that mean? It means there’s a chill in the air, the snow is falling, and romance is in the air. What is fall if not the perfect time to fall in love? Whether you’ve been together for five months or five years, we have some perfect date ideas to crank up the heat, even as the temperatures drop.

A trip to the local farm

We know what you’re thinking, isn’t a trip to the farm a fall activity? And to that we say, why would you want to visit a popular destination during its peak season? Odds are good that if you go in October, your desired destination might be overrun with crowds – and there’s nothing less romantic than crowds. How can you and your date share a romantic moment as you reach for the very same apple if you’re surrounded by strangers? How can you nail that cute selfie if you’re surrounded by potential photo bombers?

Our advice? Arrange for a private tour of the farm, late at night in the dead of winter, after everyone’s gone. This way, you can have the most authentic experience possible. Plus, you should make sure you really get to know the farmer, especially if they live all alone, secluded in a rural area. We all know how solitude can drive a person crazy! Allow them to regale you with stories about and mumblings of their missing wife and kids. And why not ask the farmer to join in the corn maze so they can snap that perfect date night photo. If the farmer starts chasing you through the maze, keep running! It’s all part of the fun. Breathe in that crisp, night air for perhaps the last time and really take it all in.

Visit a historically significant building

Winter is the perfect time for getting acquainted with your more cultured interests. We all love a good museum, but they can be crowded and expensive. It’s easy to forget how many beautiful, historically significant buildings surround us, whether you’re in the Big City or Small Town America. In your very own neighborhood, you could find a gorgeous, one-of-a-kind abandoned Victorian or Gothic home. If you’re looking for a creative (and free!) date idea, why not take a trip over? The two of you can stop to admire the home’s original features and marvel at the way people lived in the past. Don’t let the locked door or “condemned” signs deter you. Walk up the creaky staircase and through the abandoned rooms, breathe in the dust. If you squint, we bet you’ll actually be able to see the last tenants of the house for yourself! And why not introduce a little role play? Really immerse yourselves in the part and pretend to be people from the past. Before you know it, you’ll feel just like them – you’ll be talking like them, acting like them, maybe even dressed like them. Who knows? The two of you may even love the house so much you end up staying forever.

Have a quiet night in

As the temperatures lower, what’s better than a quiet night in? Open a bottle of wine and get intimate! With no distractions, the two of you can really get to know each other. Unfortunately, we live in what’s far from a distraction-free world. No matter what you do, something always comes up and interrupts an otherwise romantic evening. Our solution? Cut all the power in your house and see what happens! Hide your phones somewhere you won’t be able to get to them. Bury them, put them in a lockbox and lose the lock, maybe even destroy them entirely. Whatever it is, just make sure they’re absolutely inaccessible, no matter what happens. It’s not like there’s going to be some emergency or something. And don’t stop there – throw out your candles, flashlights, everything. Sometimes, in the darkness, you can see that much more clearly. Whatever sounds you think you hear, or if you begin to suspect someone else is in the house with you, you’re probably being paranoid. Don’t let anything derail your perfect, quiet date night. Keep the lights out and the phone cut no matter what.

Throw a small, intimate dinner party

Sometimes introducing your new love interest to the rest of your friends can be intimidating. No matter what, there’s going to be a ton of pressure on each of you. To combat this, we suggest you throw a quiet dinner party so your guests can really dig in and become pals. An easy way to break the ice is by playing some fun games, like Pictionary or charades. Or take things even one step further with a more revealing game like Never Have I Ever or Two Truths and a Lie – you want your significant other and your friends to really get to know each other, right? That means you’ve got to delve deep, with incredibly personal and revealing questions. And no matter what you do, make sure you keep the alcohol flowing, so that everyone can feel as loose as possible. Who cares if glasses get broken or plates are thrown? Conflict is a key part of forging new friendships. If you notice that one by one your friends start to go missing, it’s probably fine! Give them their me-time and don’t chase after them. Don’t forget: screaming loudly is a key part of stress relief.

Take a weekend away

It’s a truth universally acknowledged that there is nothing better on a clear winter day than a long drive upstate. Listening to music in the car, watching the scenery change – it’s like something out of a Taylor Swift song (the Folklore and Evermore albums, to be specific). For some true one-on-one time, rent a room at a bed & breakfast for a long weekend away. But sometimes the journey can be even better than the destination. Keep your eyes peeled during the drive upstate for a local farm stand to stop by, or snowy trails you can wander. If you really want to impress your friends, take a step off the beaten path and pay a visit to a closed sleepaway camp. There won’t be another soul in sight. You may find yourself so taken with the campgrounds that you forget about your bed & breakfast entirely. Suddenly you’re so rejuvenated that someone could easily mistake you two for teenage camp counselors. In fact, if a person with haunted eyes or even a sentient animal asks you as much, go along with it. No matter how menacing they may seem, we’re sure they mean it as a compliment.