Those words come across your screen, “Hey there, how would you like to meet up on Saturday?” Your heart pounds a little harder, your palms start sweating, and your mind races into a thousand different directions. After you come back down to the real world again and gain the courage to respond to your potential suitor, you are 96% sure that grabbing a drink will be suggested. I mean, the idea of a sober first date is terrifying to some.

It’s an easy way to get to know someone and you have the help of liquid courage to make you loosen up a little and just go with the flow. That’s great and all, but maybe you aren’t a drinker? Maybe you are sick of having the same date over and over? Maybe you aren’t looking for something easy tonight and want to actually give this person a chance? Maybe it’s as simple as you want to do something that doesn’t involve a dim space and a bar stool?

Regardless of your reasoning behind wanting to get away from the bars, there are many options that are laid back enough, yet entertaining enough to break the ice quickly.

Kayaking or SUP

Being outside is a fantastic way to spend the day. It is energizing and the complete opposite of spending the day in a dark bar. Seeing the sights from the water is enough to inspire good conversation. Plus, it secludes you enough to give you quality alone time to get to know someone. Kayak Chicago offers both rentals and guided tours of Chicago’s river and lakefront. Chicago SUP has everything necessary to outfit you for a relaxing paddle on Lake Michigan.

Mini Golf

This is something that everyone can enjoy. A little nostalgia in a date can ease the original awkwardness. Not only is putt-putt entertaining, but the right course can provide enough challenges to inspire some laughs. Novelty Golf and Games provides an outdoor course, along with batting cages, an arcade and a little shack to grab some grub at. Putting Edge provides a surreal experience indoors. Their 18-hole course turns the lights down and kicks on the black lights. The course looks like something straight from Alice In Wonderland. Vibrant colors and funky shapes everywhere.

Go Karts

Go Karting provides a ridiculous amount of fun, with just enough competitiveness to make things interesting. K1 Speed offers one of the best tracks around. Their professionally designed courses and quick karts makes for an aggressively enjoyable time. Their lobby is huge, with couches spread out– and a food court to grab a bite to eat.


It seems like bowling isn’t complete without a pitcher of beer on the table, but let me fill you in on a little secret– it is quite enjoyable completely sober if you choose that route. Taking your time tossing balls down the lane provides enough time to fit in conversation, while being in a fast paced setting. 10 Pin Bowling Lounge combines bowling with high-quality entertainment in the form of state-of-the-art lanes with massive screens to keep your eyes entertained. They serve up some pretty satisfying food as well.


If you want to show off your smarts, your appreciation for paintings that don’t make sense, or indulge in some insight into our world– museums are a sure winner. With plenty of options to choose from, you can find a genre that suits you perfectly. The Art Institute of Chicago covers all genres of art, and may even lead to a little inspiration of your creative side. The Field Museum is perfect for nature lovers and look into the process of the world around us. Shedd Aquarium is enough to blow your mind. Being able to view underwater creatures like you’ve never seen before will suck you in for hours. Plus, it is easy to strike up conversation while an iguana is sticking its tongue out at you. Adler Planetarium is a look into the very mysterious universe. If you are looking for deep conversations about how small we all are and to find out your date’s view on aliens, go here.

Thrift Shopping

To the right people, a date at a thrift store can be a ridiculous amount of fun and hilarity. Make a game out of it. See who can create the most ridiculous outfit for $25 or less, then proceed to wear those clothes to your next destination. Goodwill is close to the heart of the city, and their inventory almost never disappoints.


The zoo always provides easy ways to break the ice. I mean, how can your heart not melt when you see the cute little otter faces. With Lincoln Park Zoo and Brookfield Zoo providing an ample amount of sights, from animals to nature– it would be hard to leave without a smile on your face.

Dance Lessons

Not only are dance lessons fun, but they provide a skill set that you can take with you throughout life. I mean, you need to impress your grandma at her 80th birthday polka party after all. If you can’t dance but you still enjoy the dance floor (like me), this is one of the most fun past times. The last time I did this, my date was more exhausted from laughing at my failed attempts to line dance more than she was of the actual dancing. I’ll chalk that up as a success.

Chicago Dance is more than experienced to take on your dancing endeavors.


This may be somewhat of a cliche date, but there is a reason for it. Food, outdoors and good company– sold. Chicago is full of beautiful parks, which makes this a breeze. Northerly Island is wide open and provides amazing views of the skyline. Maggie Daley Park will also be an amazing location once renovation is complete. Accompanying it with a bike ride would be the icing on the cake.


Fishing actually compliments a picnic very well. Even if you don’t catch any fish, fishing is relaxing. It doesn’t take much effort, and it is a unique way to spend the day. Toss out your line, watch the bobber float and soak up the sun while you indulge in conversation. There are plenty of fishing locations to hope for tight lines at.


Tours are also an easy way to strike up conversation. With the newly bestowed knowledge that is fed to you, it can inspire conversation (and jokes) of your own. There is a tour suited to everyone. Shoreline Sightseeing provides some of the best views of the city from the water, along with dinner cruises. Catch a fireworks cruise to make it real special. Chicago Food Planet takes you around to taste some of the best food in the city. If you can’t have fun while eating, please recheck your priorities. Bobby’s Bike Hike offers both bike and walking tours that range from food experiences, to an insight of Chicago’s gangster past.


A coffee date is probably one of the most relaxed versions of a first date out there. Public setting, no pressure– just conversation, caffeine and pastries. To make it a little more interesting, find a coffee shop that also has live music playing– better yet, bring a board game with you. Uncommon Ground is a prime location for this– plus, organic food.


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