14 Valentine’s Day Date Ideas

14 valentine's day date ideas for that someone special and your bestie


Valentine’s Day is just around the corner once again! Whether you’re single or in a relationship, Valentine’s Day should be a wonderful day full of love! I always looked forward to crafting and exchanging Valentines with my friends, the chocolatey sweet treats and the general feeling of love in the air. When I was younger, the boxes of themed Valentines you could buy at the drug store were so much fun to pick out each year, but I loved making my own as well!

Sometimes I like to get creative. When I first started dating my now boyfriend back in college, I wanted to give him something special but didn’t have a lot of money. You can’t exactly give a guy a bouquet of flowers, so I decided to make a special kind of “bouquet” for him. I bought a terracotta pot and some wooden dowels at the hardware store. I filled the pot up with some dried moss from a flower store, and then I hot glued some of his favorite “things” to the top of each dowel. Some examples were fun-sized bars of his favorite candy, tiny bottles of his favorite whiskey, the chapstick he loves (and is always losing), and even a few cigars. Then I stuck all the dowels in the moss, and dressed it up with some stenciling on the terracotta pot and a ribbon around the “stems” of the “flowers.” It was a huge hit – I wish I still had a picture of it – maybe I will recreate it next year!

As much as I love giving (and receiving) Valentine’s day gifts, this year, I’m more focused on having a fun experience with the ones I love. Memories last forever, so it’s always a good idea to create fun new memories together. Whether you want to spend time with that someone special or with your best girlfriends, here’s a list of some of my favorite Valentine’s Day date ideas.


With that someone special:

  1. Restaurant crawl – it’s always fun to make a dinner reservation at a swanky restaurant, but we love sitting at the bar. We can be closer side by side at the bar, and we love the more casual experience. Besides, if you don’t have a dinner reservation by now, it might be hard to get one for Valentine’s Day! You will usually still be able to score a seat at the bar though! Try bouncing around to a few different restaurants and ordering an appetizer or small plate at each one. It’ll be so much fun to try a few different things together, and you can knock more restaurants off your list. It’s best to head downtown where you’ll be in walking distance from lots of options. In Boston, our favorites for this are: Eastern Standard, Island Creek Oyster Bar, Barcelona, Eataly, Earls, Tiger Mama, Hojoko.
  2. Cook dinner at home – it’s always so much more cozy and intimate at home. Plus, no matter what, the food you cook together will always taste better than at any restaurant. Look up recipes together and then go out to shop for the ingredients. We love tag teaming a delicious gourmet meal, and sampling along the way. This is one of our favorite things to do on special occasions, like anniversaries, and regular days as well.
  3. Couples massages – honestly, nothing beats this. If you want to really treat each other, book a couples massage! Spending time together and taking the time to relax and rejuvenate yourself is like killing two birds with one stone!
  4. Pack a romantic picnic – if you are lucky enough to live in a warm climate, pack a delicious cheese spread, a baguette and some jam or tapenade and head to a local park. If you, like us, live in Boston or another chilly locale, you can still pack a picnic. Just take a drive to watch the sunset from the warmth of your car, where you can still enjoy your picnic.
  5. Take a cooking class – again, we just love cooking together! Why not try something really out of your comfort zone and have a professional teach you something new! The best part is that you’ll take these newfound cooking skills (I recently learned how to julienne at a class) home and put them to good use for your next homemade feast. Sur la Table has lots of fun Valentine’s class options.
  6. Tour a chocolate factory – Valentine’s Day is basically synonymous with chocolate, right? Well, why not tour a chocolate factory and snag some tasty treats along the way. You can book a tour of the Taza chocolate factory here. Trust me, you’ll want to take home some quality chocolate goodies home with you for snacking later.
  7. Take a staycation in your city – a mini vacation without having to travel at all! Book a night in a favorite hotel for a little getaway. Dine at a local restaurant and then grab a drink at the hotel bar. You can even treat yourself to room service in the morning – nothing beats breakfast in bed. My favorites for this are the Charles Hotel and the Revere Hotel.

With your besties:

  1. Book a spa day – you don’t have to be in a relationship to get a couples massage. My sister and I have actually gotten them together! Either way, you can schedule massages and facials for the same time and enjoy the rejuvenating treatments together.
  2. Get manicures together – continue the spa day and pamper yourselves, together! Or, if Valentine’s Day falls on a busy weekday, like it does this year, book an after work appointment with your bestie.
  3. Go on a shopping spree – who doesn’t thrive on a little retail therapy? You’ve most likely got an event coming up for which you need a dress, so grab your bestie and shop ’til you drop! Or, better yet, raid each other’s closets! Something you’re ready to get rid of just might be a new statement piece for your bestie.
  4. Have a bestie brunch – no one said you have to celebrate Valentine’s Day on the 14th. Make a reservation with the girls for this weekend and head out for bloody marys and mimosas in honor of the holiday of love.
  5. Go out to dinner – book a reservation at a restaurant you both love. Long before my bestie and I had boyfriends, we had a standing Valentine’s Day dinner date at Max Brenner’s chocolate factory. You might think it’s lame, but we loved it! Funnily enough we even signed the lease for our first college apartment together one Valentine’s Day after our Max Brenner date. So, we definitely have special memories of this tradition.
  6. Make a DIY hot cocoa bar – invite your favorite ladies over to sip something warm and chocolatey. Check out this post for all the details on how to put together the prettiest hot chocolate bar, with lots of yummy treats for accompaniment.
  7. Go out for thai ice cream rolls – because there’s no shame in spending V-Day getting that perfect, insta-worthy shot. No one but your bestie will understand better, so grab her and head to the newest trendy spot to enjoy something sweet and capture the moment.


14 valentine's day date ideas for that someone special and your bestie

How will you be spending Valentine’s Day this year? Whatever you do, be sure to have fun and spread a little love!

Happy Valentine’s Day!

xo -L

The Lilac Press

Say Hello!