Boston is a great city, no doubt about it.  But with greatness comes competition, and let’s be real -- there are tons of smart people outdoing each other in anything and everything here.

So you’re struggling to impress your date with something more unique than whatever the person they dated before you was able to whip up. You can’t go too extravagant, that would scare them away, but just because you didn’t attend Harvard Law doesn’t mean you can’t be witty and smart when it comes to winning over their heart.

Time to put on your thinking cap, and if you need a little push along the way -- here are a few fun ideas for you to consider.


Set My Heart Asail


Ahoy, matey! We’ve all had that secret fantasy of dating a sailor at one point or another. Who wouldn’t - Hollywood movies paint them as the perfect gentlemen; with manners unlike anyone else and striking looks like Clark Gable. Whether it’s reality or not, we don’t really care, do we?

Take your date back in time and embark on this Rum and Revelry Sail by Liberty Fleet of Boston, with period actors and musicians entertaining you throughout the night. Watch the Boston Harbor glisten as you sail by with your boo in one hand, and a drink in the other. Be the sailor of your date’s fantasies.

Liberty Fleet of Tall Ships

Freedom Calls


Follow the trail of crumbs *ahem*-- freedom -- follow the trail of freedom as you make stops at local favorites and taste some of Boston’s finest delicacies on this mouth-watering adventure.

This tour will be a fun mix of food, history and exercise. Do you really want to go to a restaurant and stare each other in the eyes awkwardly, when instead you can go on a fun walking tour together? Of course not, so try this on for size instead.

Yummy Walks

I Love Brew


Going to a pub to meet your date is kinda lame. But a fancy wine-and-dine is just not what sparks your flame. So you wonder how to incorporate the relaxed beer scene into your date... Consider this problem solved!

Boston is known for its beer scene, so take it up a notch and instead of hitting up the corner pub -- embark on a beer tour! New England Brewery Tours will make you look sophisticated and adventurous enough, plus you’ll get to enjoy your beloved brew. Two birds, one stone!

New England Brewery Tours

Laugh With Me


Laughing together on a date makes you feel more connected, which in turn, will more likely score you a second one. No seriously, this has been proven by scientists. So it would only make sense to expose the both of you to guaranteed laughter, right?

Take your darling boo to Just Suspects Open Mic Comedy Show, and start connecting.

The rest is up to you -- but this should be a good start.

Just Suspects

En Gard, My Heart!


The art of fighting is a skill every individual should learn. Especially if you’re two individuals trying to navigate your way through the curves of something called dating. Yikes!

Eventually, you’ll become the master of your own game and you’ll hopefully learn what “fighting fair” means. But hold your horses -- you’re not there yet.

In this fencing class, you and your date will learn the sophisticated way to fight. This sport has a regal touch to it, so perhaps after breaking some sweat with your swords, you can go and have a delightful afternoon tea together.

Olympia Fencing Center