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20 Unexpected Valentine’s Day Date Ideas to Make Your S.O. Smile

When the second week of February rolls around each year, Adam and I inevitably look at each other a little bewildered and ask “So… what should we do for Valentine’s Day?” Most of the traditional ideas can feel a little cheesy (not to mention overpriced), so I’m always on the hunt for unexpected Valentine’s Day date ideas that will still feel romantic and special.

I remember the first year we celebrated Valentine’s Day as a couple, we cooked a really fancy dinner at Adam’s place complete with steak and chocolate soufflés, and it was so memorable that we’ve tried to do something outside the box every year since. Whether you’re coupled up or single, keep scrolling for 20 unique ideas that will ensure your Valentine’s Day is actually fun, with no clichés in sight.

Date Idea #1: Find and go to a drive-in concert. 

Bonus points for dressing up and bringing your own lawn chairs and snacks.

Date Idea #2: Create a private movie theater in your house with a projector and screen a romantic movie.

Just add popcorn, Raisinets, and two pairs of cozy socks.

Date Idea #3: Go roller skating.

Or ice skating. The goal here is to channel your favorite hand-holding scene in just about every classic rom-com.

Date Idea #4: Host a karaoke night in your living room. 

This personally sounds like my vision of hell, but I know it’s right up some of your alleys. Plus, if you were born with the voice of an angel, this could be a great strategy for making him/her fall in love with you on the spot. If you want to be super professional with it, check out this Wireless Bluetooth Karaoke Mic.

Date Idea #5: Take an early morning hike to watch the sunrise.

I know, I know – sounds kind of painful. But there’s nothing more magical than watching the sun come up, and getting up that early to break a sweat is a totally bonding experience.

Date Idea #6: Host an at-home art night. 

Whether this means sketching in an adult coloring book, making a collage of your favorite photos together, or streaming an artist’s documentary, get your creative juices flowing.

Date Idea #7: Put together care packages for the homeless. 

Stuff paper bags or shoe boxes with food, water, socks, hand wipes, etc. and keep them in your cars for the next time you drive past someone in need. It’s pretty cool to see your S.O. serving others and sacrificing his free time for a worthy cause. You’ll likely fall in love with each other all over again.

Date Idea #8: Take a virtual cooking class.

Bonding over pots of marinara and pans of tiramisu? Sign me up!

Date Idea #9: Schedule a tasting at a winery or brewery on Zoom.

We love visiting wineries and are missing our little excursions. This year, I want to plan a virtual tasting where we can have the wine shipped to our home and recreate that feeling. Another fun activity is to buy three bottles of wine: one that is $20.00, one that is $10.00, and one that is $5.00. Cover the bottles in foil and mix them around, then try to guess which is which! It’s pretty surprising sometimes.

Date Idea #10: Pick up your favorite take-out and drive to a scenic location for stargazing.

When was the last time you and your S.O. really looked at the stars together? There’s something about gazing at the nighttime sky that is such a reminder of the vastness of the universe — and how lucky you are to have found each other in it.

Date Idea #11: Take a “staycation” at a favorite local hotel.

I think every couple should splurge once in a while and spend the night away, even when a full-blown vacation isn’t in the cards. Order room service, watch a movie, jump in the hot tub, and sleep in.

Date Idea #12: Take a virtual dance class.

Check out YouTube instructors that offer salsa or swing instruction. Perfect your dance moves for the next time you go to a wedding or a country bar.

Date Idea #13: Recreate your first date.

For Adam and me, this would involve a dive-y Chinese restaurant, Peking Duck, and one too many glasses of chardonnay. If you’ve been together a long time, you’ll undoubtedly have fun laughing about those early days, and it may even be a valuable reminder of why you fell so deeply in love in the first place. Be creative about how to recreate your dates at home! Pick up takeout from the restaurant, dim the lights, use tablecloths, or any unique aspects that a specific restaurant has.

Date Idea #14: Pack a picnic and bike ride to somewhere special together.

There is something so special about riding bikes together to a special spot to indulge in a picnic together. Pack your favorite cheeses with dips and snacks in a picnic basket—don’t forget the bottle of wine!

Date Idea #15: Explore a local bookstore.

You don’t have to be a bookworm for this to be a best-ever date (although, bonus points if you are). Head out and browse the stacks! Select a read for yourself or pick one for your partner. When you get home, curl up on the couch and read side-by-side. Nothing like a little literature to set the mood.

Date Idea #16: Make breakfast in bed.

Nothing beats feeding each other bites of pancakes while you’re snuggled under the covers. Whether you want something healthy and vibrant or are craving your favorite comfort food (again, pancakes), as long as you’re getting in the kitchen together and sharing a meal, you really can’t go wrong with this date.

Date Idea #17: Travel by train.

This idea might be a little more involved, but it’s nothing a little planning can’t make happen. Train travel lets you take in your surrounding sights in the most relaxing way possible. You don’t even have to set out with a specific destination in mind—it’s all about the journey.

Date Idea #18: Theme your date night.

Date nights are great and all, but when you center it around a specific theme, you can immerse yourself in a whole new experience. And of course, nothing says romance like a little jaunt to France. Want all the Parisian vibes without having to get on a plane? Make a playlist of all your favorite French music, plan out a French-ified menu, and transform your dining room into the chicest French restaurant, no matter where you are.

Date Idea #19: Make a vision board.

Sharing your dreams and setting the foundation for future plans to come is the ultimate way to connect. You can each create your own vision board or collaborate on one together. It’s a fun and inspiring process, and can guide conversations for what you each want for yourselves and your shared goals as a couple. For steps on how to get started, read our guide to vision boarding here.

Date Idea #20: Camp it up.

While a get-lost-in-the-woods date can be just the adventure many of us are looking for, there are others who’d rather camp out in the living room. Whether you were a scout in a past life or have never spent a night in the great outdoors, there are plenty of ways to tailor this date for a magical evening (hello, glamping). Just don’t forget the marshmallows.

This post was originally published on February 9, 2020, and has since been updated.


Camille Styles

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