29 Romantic Winter Date Ideas

Winter already, eh? You guys lovelovelove date ideas around these rosy parts, so I’m bringin’ some of the best for fun, affordable, romantic winter date ideas today. #hollah.

It’s went from being in the 60’s around Christmas to feeling sub-zero reaaaaaaal quick. I think Mother Nature was just trying to perfect the fashionably late entrance, like I’M HEEEERE! WINTER IS HEEEEEERE! Lol Mother Nature, the joke is on you. Because I’ve got 29 ridiculously romantic winter date ideas to give you all the feels this season, even if you’re just feelin’ freezing and you’re hanging out with your besties and cats every Friday night.

29 romantic winter date ideas | Not sure what to do for a fun Friday night date when it's freezing cold outside? These 29 winter date ideas are romantic, fun, unique, and affordable! Click to check them all out. - 29 Romantic Winter Date Ideas featured by popular Philadelphia lifestyle blogger, Coming Up Roses


  1. Go for a stroll. Pick a brisk, chilly evening (easy to do if you live in the Northeast), bundle up, and head out, hand-in-hand of course with your favorite person.l If you can do this while snowflakes are falling, you win! It’s also a great adventure in the evening after a new fallen snow – everything is white and sparkling – and there’s still silence that you won’t find any other time.
  2. When you return from your stroll, treat yo’selves to hot chocolate. And not the instant just-add-water-in-a-packet stuff, but the real deal with milk and cocoa, in a pot that you heat up slowly. Extra bonus points for marshmallows to top off your mugs. Because as we said before, the bigger the marshmallow, the closer to God.
  3. Have a blackout! Do like you would in a power outage and get creative. Disconnect the lights, unplug, light some candles, and tell ghost stories on your living room floor.
  4. Make cookies. Go as simple or as sophisticated as your baking skills allow, but roll up your sleeves and grease up those sheets.
  5. Make lots of cookies – and give them all away. Use bags or boxes or little plastic containers, pack up the cookies, add a pretty bow (sparkly, of course), and start delivering. Enjoy the surprised looks on the faces of your lucky recipients!
  6. If  Mother Nature cooperates, make snow angels, build a snowman, and go sledding – let your inner kid get out and play!
  7. Invite friends over for charades or old-fashioned board games (think Monopoly!).
  8. Plan ahead for Valentine’s Day! Buy a multi-pack of Valentine’s or make your own for all your family and friends and anyone who would enjoy a little love. Get two of the giant Valentine’s and write them out for each other!
  9. Find an arcade that still has old-time pinball machines. Bring a bunch of quarters and have at it – then share a large malt or milkshake with two straws.
  10. Have a pajama party in your best blanket fort. Get on your jammies and deck the living room out in your best fuzzy blankets and pillows for one heckuvah epic blanket fort. Sleep under it.
  11. Plan to have a “date night in” and cook dinner together. Be as simple or as fancy as you feel.
  12. Write love letters for the future. Write them for each other, and also write one for yourself (and anyone else in your life who needs a love letter 10 or 20 years from now!). Get sappy, and when you’re done, seal them up and put them somewhere safe until it’s time to open.
  13. Host a cookie swap. Invite your baking friends and have each one bring a dozen sweet treats for every person at the swap to take home, plus an extra dozen to enjoy at the actual swap. So, if you invite 5 people, bake 6 dozen. Make enough copies of your recipe for everyone!
  14. Do a jigsaw puzzle together. This could be one date night or a few – perfect for relaxed weekday date nights to shake up the work week! If you’re buying a puzzle, pick one you love so you can glue it together and hang it up afterwards.
  15. Paint the snow! Water + food coloring = SNOW PAINT. Head outside and get to work. The best masterpiece wins a back rub.
  16. Pretend you’re tourists in your own city. Typical open-bus tours might be a bit chilly in winter, so make sure you’re IN something and tour your city’s most touristy sites and attractions. Pick up your city’s most iconic dish to eat!
  17. Read together! But not each reading individually. Pick one book and take turns reading it aloud to each other. Hit up the library beforehand and grab a few options, and make it like a mini-book club for just the two of you! Added bonus: choose a variety of genres. If it’s a funny fictional read, use your best accent. For a more historical account, sound prim and proper. Have fun with it, too!
  18. Go around the world in one night…with dinner! Come up with a 5-course menu that works its way around the planet. Start with an appetizer from Italy (I’m all about carbs, so breadsticks it is!), then try a soup, salad, entree, dessert…all from different cuisines. Make your own or order in, so long as it’s diversifying your taste buds!
  19. Pick an old TV sitcom from another decade and bingewatch it (nix the Netflix!). Something like Happy Days, Murder She Wrote, Perry Mason…etc.)
  20. Do a Mall Date Dare challenge. Make little scorecards and come up with 5-7 dares or challenges at the mall. Example: Find a book of yoga poses and start your practice…in the store aisle! Assign different point values for each dare and a coveted prize for whomever racks up the most points.
  21. Chinese + a movie. You can’t go wrong. An added twist: empty your purse, grab takeout, and hit up the movie theater with your egg rolls and fortune cookies. J and I have done this before, and it’s the coolest alternative to popcorn. Just combine dinner and a movie altogether!
  22. Buy a puzzle book, like crossword puzzles or word search. Tear our sheets to compete against each other, or do the most challenging one in the book together.
  23. Host an at-home spa night together.  Set up opportunities to earn “Spa Bucks” throughout the week by doing different nice things for the other person or carrying out household chores. By Friday night, you can each cash in your Bucks for different Spa services, from a mani/pedi or massage to a bubble bath and champagne. Bonus points for having chocolate on-hand and whipping up some spa water (cucumber, orange, and berries all work great!).
  24. Warm up by working out…together. Sometimes breaking a sweat together is just hella romantic. Hit the gym and get to work on those New Year’s fitness Resolutions! Do a few reps together for added encouragement.
  25. Play the Newlywed Game and test your trivia of each other. This printable will help you get started.
  26. Set up your own photobooth with your computer or tablet. Go all out with your best feather boa, oversized glasses, funky hats and props. Take snapshots like you would in a traditional photobooth, and print them out in little squares as souvenirs of your date night!
  27. Relive fall with indoor s’mores and homemade pumpkin spiced lattes. It may be too cold for an outdoor fire pit now, but you can actually get a lot done in the microwave. Make your best gooey s’mores, then pick up the ingredients for your own favorite hot fall drink. Cozy reminiscing!
  28. Have a pillow fight. Loser buys brunch the next morning.
  29. Host a beach blast party…indoors. It might be freezing outside, but throw on your swimsuits, lay out your towels, pour some tropical coladas and cocktails and blast some Jimmy Buffet.

29 Romantic Winter Date Ideas featured by popular Philadelphia lifestyle blogger, Coming Up Roses

BONUS: Try a new local, authentic, hole-in-the-wall restaurant. J and I double dated last night with one of my best friends and her boyf, and we got the most *amaaaazing* Venezuelan arepas. And added bonus was how cheap the whole place was! Scour Yelp for highly-rated, inexpensive places to try, and bring friends. (:

What about you? What are some of your favorite winter date ideas?

You’ll also love:

30 Romantic Fall Date Ideas

22 Cute & Cheap Summer Date Ideas

12 Dates of Christmas

Halloween Date Ideas (for the couple that hates Halloween!)

How we Met

3 years, 6 tips [+ Engagement Photos!]

What would you love to do on a winter date?

Leave your own romantic winter date ideas in a comment below, because J and I have a few open weekends to fill from your suggestions!