It’s almost Valentine’s Day!

Planning dates can be hard. Especially during the winter. And our most iconic date night of the entire year is in February. So if you’re looking for a few ideas of how to beat the cold, but do a little something more than just dinner and a movie, here are some of my favorites!

All these dates are flexible and if you’re single, you should definitely still do these with your friends! I’ve done these with my girlfriends, my boyfriend, and now my husband – so of course adapt these ideas to your company!

The Classic Date

If you love to dress up, if you love the arts, and if you’re a romantic, this is the date for you.

A classic, fancy date can be so much fun! Dress up, go to the theater, and splurge on dinner.

You can start out with a simple google search of musicals, plays, orchestras, ballet, productions, and events in your area.

Last valentine’s day my boyfriend took me to see the musical Annie and we ate Italian by candle light then exchanged our gifts and letters. It was simple but felt so perfect and romantic.

If you have more time earlier in the day, go to an art museum!

Art museums are super romantic and foster great conversation. Art inspires and creates a perfect opportunity to get to know your date. As you walk through, ask your significant other which pieces are their favorite, why, and what they see in the piece.

A lot of art museums have cafes that you could enjoy a brunch in beforehand and a gift shop you can browse afterwards. If you picked up on your date's favorite art piece, buy them a postcard of that painting from the gift shop to take home.

Whatever you choose to do, enjoying art and good food is always elegant, stimulating, and fun to share with someone you love.

The Cozy Date

I feel like this is the classic Tumblr/Pinterest date – but 100% not overrated.

Build a fort in the living room with Christmas lights and play games or watch a movie. Make it comfortable – a lot of guys might not feel like sitting on the floor for several hours after a long day at work, so think about creating a canopy over the couch or at least using the couch cushions to make a substantial seat on the floor.

If you want as much time as possible to talk and relax – order in pizza or carry out sushi. If you don’t know each other as well and it’s more comfortable to interact over an activity, make homemade pizza or try your hand at sushi together, as part of the date.

Whatever shape this date takes, it’s always fun, cozy, and means a lot that your significant other would go to the effort of setting something up for you.

The Active Date

Maybe you’re the type that loves to have something to DO together. It can be a challenge during the winter to find activities indoors but if you’re wishing for something active, here are some ideas.

Bowling, figure skating, and rollerblading are some fun low key indoor sports. If you want to get a little more active, try laser tag or go karts. If you’re feeling really energetic, indoor rock climbing or a trampoline park can create some unforgettable memories!

Once you’ve worked up an appetite, there’s nothing better than a hearty burger, fries, and milkshake afterwards from a local diner.


If you love traveling but don’t have the time or budget to book a vacation for date night – I’ve got something for you!

Pick a location, theme, or experience and get creative – make it feel like you’re traveling without ever leaving the county.

Here are a couple examples of things we’ve done.

Italian Date Night

Go to Olive Garden for supper and pretend you’re in Italy. Talk about the food, the culture and imagine your walk home through the cobblestone streets back to your Airbnb – maybe even learn a few phrases in Italian.

On your way home, stop at the grocery store to pick up some syrups, seltzer water, and heavy whipping cream to make Italian sodas when you get home. Cozy up with your drinks and watch a movie set in Italy – The Italian Job, Letters to Juliet, Under the Tuscan Sun, etc.

I promise, this will be so much fun. Unless your boyfriend has no imagination. In which case, you should probably dump him. Just kidding. But think about it.

Road Trip Date

I don’t know about you, but for me, some of the best conversations happen in the car. I think there’s something about the confined space of a car that can create a safe, relaxed space for talking. Some of our best conversations happened on road trips, parked on the street in front of my apartment, or on the way to a social event.

So pack some snacks, create a playlist, and go on a road trip through your own town! This was honestly so much fun and the possibilities are endless! Start out the same way you would when you’re going on an actual road trip – strap in, cozy up with a blanket, start some music, and get some coffee for the road. Don’t feel like you have to plan a specific route, just drive around wherever the road takes you. Stop to take photos by significant signs (maybe your town has a welcome sign), go through as many drive throughs as your heart desires, and see if you can find something new you’ve never seen before.

We drove around to the back of our town, found a spot to look out over all the city lights, turned off the car, and talked about different parenting methods while we enjoyed hot drinks.

It was so much fun just enjoying each other’s company, good conversation, fries, playing songs for each other, more fries, seeing the city lights with music, the heater, tacos, more fries, etc.

Bonus: Outfit Inspiration

Here are our picks for Valentine’s Date 2020 dresses!

The ‘Shelby’ striped turtleneck dress in black:

And the ‘Sasha’ sweater dress in Grey:

Why these dresses are perfect:
  • Cozy, long sleeved, turtlenecks for winter
  • Cute, simple, classy
  • Can easily be dressed up with a hat or cardigan for formal dates
  • Can easily be dressed down with slouchy socks or a beanie for casual, cozy dates

If these ideas inspired you, we want to see! Post a photo and use the hashtag #MSEDATE on any social media platform.

Everyone can check out the hashtag to see what your girls are up to!

Have fun! XOXO
February 04, 2020 — Alt & Dot Collaborator

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