It’s date night again, but you and your boo thang have done it all. You’ve done all the tours, painted all the things and have seen all the sites together.  You’re tired of the same old activities, tired of the same old routine, and tired of each other (Just joking. We really hope not).

If this sounds like you, and you’re still on your search for an injection of fresh creativity, then look no further. Us good folks at Vimbly have just compiled 6 creative date ideas that you and your date could surprise yourselves with.


A (Glass) Token of Love

glass blowing

Who knew glassblowing could be romantic? There’s something about slaving over a hot kiln together that gets the endorphins flowing. If your date has never taken a glassblowing class before, he/she will be absolutely amazed at the properties of glass before it becomes… glass.

And afterwards, you’ll have an awesome little trinket or two that will stand as a token of your love! Just be sure to build it sturdy. You don’t want it to break!

Find out more Ignite Glass

I Saw Fireworks


It’s not enough that when you surprise your sweetheart with a Segway tour, you’ll both get a thrill from learning a new activity. It gets even better than getting to see fun attractions in your city in a new light, such as The Field Museum and Millennial Park, and learning new stories about them as you go -- this one ends with fireworks.

We trust you’ll know the right time to land that romantic kiss. Just remember -- both hands on the Segway at ALL times!


Find out more City Segway Tours

Two Cliches, One Tour


The Notebook showed you the magic of a romantic boat ride. Every other romcom showed you the magic of basking in the golden glow of the setting sun with your love. Now you can combine the two on this sunset kayak tour of Chicago.

Watch the beautiful city - and more importantly your beautiful date - slowly become a gorgeous silhouette against the backdrop of a sky of liquid gold as you paddle down the river of love (it’s actually the Chicago River, but come on, when you’re having a romantic time on any river it’s a river of love, right?)

Find out more Kayak Chicago

I Like Your Face


Painting classes are such a go-to date idea. By now even you might have a couple paintings that you cobbled together on a date or two. Step your art game up and learn how to draw portraits this time around.

Why would that be different, you ask? Apart from learning how to create an piece of art with entirely different materials, you’ll have a great time trying to draw each other. Especially as the alcohol starts flowing.

Let your love for your partner guide the pencil/charcoal/ink and show your partner how you really seem them on the page (just don’t tell them that if the portrait doesn’t end up looking like them).

Find out more One Strange Bird

Bye Bye Boring Dates


Ah, the theatre. What a sophisticated, classy place to fall in love in the beautiful city of Chicago.  Long, serious dramas are perfect if you’re looking for a place to sit silently next to each other without any chance to converse. Perhaps you’ll leave the date without even knowing your partner at all!  

But fear not, you can attend a show and get to know your date all in one fell swoop.  Don’t sit through a long show with no chance to show off your charm, wit, and downright STUNNING personality.  Instead, attend Bye Bye Liver, a comedic show centered entirely around alcohol, that gives you the chance to participate in the hysterics and win the heart of your date.  

You’ll laugh yourself to tears as you hear story after story of drunken tales, which might just inspire you and your date to continue your night and make some new stories of your own.  


Find out more The Public House Theater

Find Your Soymate


Is that love you smell in the air or is that just raw fish? Well, everyone knows they’re one and the same.

Show your bae how you roll (your sushi, that is) in a sushi making class that shows you have to make a delicious meal from scratch. Side by side, you and your date won’t help but feel sparks when you see what an amazing dinner you can make with each other. Learn to use bamboo mats to make any sushi roll you can dream up, and then share in a spectacular culinary experience as you dine together on your creations.  


Find out more What's Cookin, Chicago?