Valentine's Day Date Ideas From Over the Years

You make it through the holiday season blur when Thanksgiving, Christmas and New Years come through and finally catch your breath, just in time to look up and realize it is the day before Valentine's Day. You forget to plan something? Or maybe you have had it circled on the calendar for weeks and still don’t know exactly what to do? Or maybe you realize that Valentines Day is just a construct by corporations to guilt people to spend some big cash during an otherwise low period in revenue?

Well, no matter what your personal take on the day is, we wanted to share some of our own date ideas that stray from the norm dinner and a movie, and some stories of us along the way. And trust me, with more than six years of dating behind us, we have had plenty opportunity to get creative!

The Beginner Move (2012)

My first Valentine's Day as part of a ‘couple’ I didn’t know what to do. We were in high school, and I wanted to surprise Samantha and make her day, but didn’t want to embarrass her or come on too strong. What I ended up doing was getting flowers in her favorite color (orange, always orange flowers) and waiting for her to get to school. What ended up happening was her coming in late that morning and me waiting in the parking lot as the bell rang, for her to finally come careening in just in time to say thanks and run to class.

The Explorer Date (2016

A personal favorite and great opportunity this year (as the weekend after Valentine's Day is a three-day weekend, thanks President’s Day) is to take a quick trip somewhere you have never been. Our secret to planning these weekends is the New York Times book series 36 Hours. Here you can flip to one of 150 cities in the US and Canada that have the best ways to spend 36 hours in. This starts Friday after work and always ties in local favorites and little known places, as well as the big must sees anywhere we go. Not only do these make a great gift, they have been fun to use, like when we made our own three-day weekend for a trip to Savannah GA and Charleston SC.

The Fast-Paced Date (2013)

Samantha's Instagram shoutout to me circa 2013

Time to shed some light on what Samantha has cooked up in the past, in what is definitely one of our most fun packed dates! For my 19th birthday (yeah I know, a long long time ago) Samantha rented two mopeds from the forever missed Campus Skooters and we zipped around town all day with each other and friends. We were so eager to show them off we even tried storing them in the dorms (didn’t quite fit in the elevator).

The "We Aren't Celebrating Valentine's Day" Date (2014)

We've all been there. For us this was a college Valentine's Day. We decided to not do anything big and just play it off like any other day. I think we ended up going to a Hockey Game on her parents' behalf, but before getting dropped back off at the dorms, Samantha gave me a tub of Kraft Mac and Cheese with a ribbon and Valentine's Day Letter. We sat on her bed with our disposable utensils sharing our Mac and Cheese.

The Secret Set-up Date (2018)- Samantha's Favorite!

These are the most high-risk high-reward date ideas. We have certainly had some crash and burns but some of our best date nights have come when one completely surprised the other. This past spring Samantha told me to walk down to the pavilion only to find a full set up with hammocks, fire (and s'more dip), lights and the idea to create a video time-capsule. With a bag full of interview questions, we set up our video camera and tripod, and interviewed each other. We would share the questions and answers, but they are stored away until 2028.

Self-timer fail, but we still like it.

The Educational Date

I know, I know, this is right up my alley and might not be for everyone but hear me out! No matter where you live, I am sure that you live close to a museum of some sort. Luckily for us, in Pittsburgh we have the Carnegie Museums, with the Science Center, Natural History, Art and Andy Warhol Museums (and we are now annual members courtesy of the best Christmas gift from Catherine). Sometimes it can be fun to go look at things from distant times and places, and just act silly together!

The Quiet Getaway Date (2017)- Evan's Favorite!

If you came to see what some of the best things we have done are, then now we are talking. To celebrate hitting our five-year mark, we headed up to the Adirondacks and rented a getaway cabin for the weekend. This dreamy riverside hideout came to us courtesy of Air BNB and Ralph Kimbrell (thanks for the CD by the way) and was greater than I could have ever imagined. We got in for the weekend and explored the area as fall was coming to a close, and had a onesie night watching Star Wars and eating ramen, sat and looked at the stars, chopped wood for a fire (that we had to light using the stove inside, terrifying), and when we woke up the final day were welcomed to the first snowfall of the year, as we got to watch the seasons change overnight. Really beautiful, even though our car got stuck for an hour trying to pull out of the driveway. If you have the time, I would recommend this to anyone and everyone.

The Last Resort Dates

Here is something we did just last week as we seemed to need something to pick us up and get us through the week. Sometimes things get hard and you need to talk things out, or hear from each other, and we turned to two markers and a few sheets of paper. We took turns filling out an answer on each sheet was passed around, with Questions written at the top like “What do You Love about the Other?” or “What makes you Happy?”. You can have some creativity here and mix in silly with serious and really work on the foundation of your relationship.

In the winter of 2013, we really didn't know what to do. We stumbled upon an ax and went to cut fire wood. This was also a "Last Resort" Date. Talk about #CoupleGoals

The Movie Date (2013)

Everyone has movie dates, but how long has it been since you spiced up your movie date? In 2013, I rented a portable battery, projector and sound system to project Samantha's favorite movie Stand By Me, in an outdoor field. Cold weather can make this hard, but maybe you can add an ice cream or popcorn bar or hot chocolate to your movie night. Maybe even go to the Library and rent a movie you really want to see instead of settling for whatever is on Netflix.

The Close-To-Home Date (2018-2019)

Sometimes what the two of you may need isn’t a big fancy trip or complex setup, just something totally easy and close to home. Our favorite for this has been going for walks along the railroad. It is easy to get lost in conversation but always easy to follow the path back home. Maybe suggest a walk, and even throw in some cookies from a local bakeshop to sweeten the deal?

No matter what you want to do this Valentine's Day, if you have someone you care about just let them know, however you think they’d appreciate. Whether that be with a surprise trip to Charleston, a moped in their dorm room or a simple card in the morning, let them know that you love and appreciate them.

Happy planning!



Featured Posts