29 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 29 unique ideas that will ensure your Valentine’s Day is actually fun, with no clichés in sight.

Featured image of Rebekah Peppler’s Parisian dinner party by Joann Pai.

Image by Michelle Nash

29 Unique Valentine’s Day Date Ideas to Try This Year

1. Find and go to a drive-in concert. Bonus points for dressing up and bringing your own lawn chairs and snacks.

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.

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.

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 them fall in love with you on the spot. If you want to be super professional with it, check out this Wireless Bluetooth Karaoke Mic.

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. Plus, getting up that early to break a sweat is a total bonding experience.

Image by Belathée Photography

6. Take a virtual cooking class. Bonding over pots of marinara and pans of tiramisu? Sign me up!

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 their free time for a worthy cause. You’ll likely fall in love with each other all over again.

8. 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.

9. Schedule a tasting at a winery or brewery. While we did this virtually during the pandemic, there’s nothing better than taking an excursion to your favorite spots. Or, if you want a more low-key experience at home, buy three bottles of wine: one that is $25, one that is $15, and one that is $10. Cover the bottles in foil and mix them around, then try to guess which is which! It’s pretty surprising sometimes.

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.

Image by Michelle Nash

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.

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.

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.

Image by Belathée Photography

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!

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.

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.

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.

Image by Christie Graham

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.

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, check out our guide to vision boarding.

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.

Image by Michelle Nash

21. Ask questions designed to build intimacy. This list of 32 questions was written specifically to help deepen your relationship. Because as the author, Nihel, writes: “With the right mindset, intention, and questions, setting aside these special moments can deepen your love and bring a fresh and renewed perspective to your relationship.”

22. Read your favorite “Modern Love” stories. Who else skims the Sunday paper’s ‘Style’ section for these vignettes of real-life romance and heartbreak? If you’re already a fan, help your partner get on board. Pick an essay from their archives and take turns reading them aloud to each other. You’ll get a glimpse into a life unlike your own, as each story is a window into unique perspectives on, and experiences with, love.

23. Get competitive. Game night anyone? Care to challenge your S.O. to a round of tennis? Whatever your competition of choice, pick it and gear up! There’s nothing like a little healthy competition to set the sparks flying.

24. Bake a new recipe together. PSA: Valentine’s Day dessert doesn’t have to involve chocolate. In fact, some of the best draw upon unique flavors and clever spins on classics. The Kitchn has you covered with its list of 40+ delicious desserts.

25. Recreate each other’s favorite cocktails/mocktails. Even if you don’t consider yourself a mixologist, you can have a little fun getting creative at your home bar. Ask (or guess!) each other’s favorite drinks and make them at home. It’s a kind gesture that will make them—and you—feel seen in your tastes and preferences.

Image by Michelle Nash

26. Play Esther Perel’s conversation game, “Where Should We Begin?” We counted down the days until the famed psychotherapist released her conversation deck. With prompts like “Share something that’s changed your worldview” and questions that ask you to share what’s been keeping you up at night, trust that there’s no holding back. Pick up your copy here.

27. Write a letter to your S.O. for them to open next year. Who wouldn’t love receiving a letter that took you back to where your relationship was the year prior? Reflect on your feelings, thoughts, and what you love most about them in this moment. It’s a touching gesture and one that you’re both likely to keep stored in your dressers forever.

28. Find out each other’s enneagram. If you haven’t heard, intentional personality tests are back. (Key word being “intentional”—there’s nothing hokey about them.) Discovering each other’s enneagrams is an eye-opening way to dive deeper into what makes your partner tick. Learn more about the enneagram—and what it says about your personality—here.

29. … or uncover your love languages. If you haven’t done a deep dive yet, understanding the love languages (and knowing which best describes you and your partner) sheds insight into you each give and receive love. We share everything you need to know about love languages here.

Valentines Day Date Ideas

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