The 6 Elements of a Great Date Night In Chicago 

Two photos of couples enjoying a date night Pickle Haus. One couple high-fiving on the courts. Another couple enjoying drinks at the bar.


When date night rolls around it’s easy to get stuck in the same old routines. Movie? Drinks? Shopping? You’ve done them all before, and while they can be fun in their own way, you’re probably eager to spice up your evening and try something new.  

Living and planning date nights in Chicago can present so many choices that it’s easy to feel overwhelmed about picking the right one. Good news: there are so many opportunities to wow someone you care about with an experience outside the norm.  

But what’s the secret to making sure your date night activity has all the ingredients for a perfect outing? How can you make sure your selection will excite, delight and satisfy your special someone? 

Whether it’s a first date or a special night out with a long-time partner – here are 6 things you can try to make a memorable date night in Chicago truly special!  

  1. Trying Something New 

Can’t remember where you left off during your last Netflix binge together? That’s because the monotony of routine can actually make time together feel less memorable. 

When you’re planning a date night in the Chicago suburbs, you might feel like you have a reliable place and routine that work for you. However, studies show that trying new activities and sharing exciting experiences together leads to greater relationship satisfaction overall.  

Picking up a new sport or introducing your special someone to a game you love is a sure way to share in the thrill of a first-time experience together.  

One of the best things about pickleball is that you can start playing and having in minutes, even if you’ve never picked up a paddle before. It’s a great, low-stakes way to experience something new and create special memories with that special person.  

  1. Exercise – An Instant Mood Booster 

Feeling a little nervous about your date?  

Getting both of your hearts pumping together is scientifically proven to help calm your nerves and actually make you feel more relaxed. When we exercise, our body produces “feel-good” hormones known as endorphins that reduce stress, elevate your mood and help you and date feel great! 

Turn that nervous energy into a warmup activity. Invite your date to stretch with you before your outing. Take turns leading a different stretch and mirroring each other’s favorites. Now you’re both ready to move together!  

Once you enjoy a little exercise on the court, you’ll be loosened up and ready for great conversation – you can keep the date going by transitioning to the bar to chat and enjoy a local beer or some craft cocktails.  

  1. Double your Date for Double the Fun 

Nothing brings people together like a little healthy competition. Whether you and your partner team up to take on another couple OR you get to compete against your crush – the experience of a little rivalry can help boost connection and confidence. 

Pickleball is even more fun when you play doubles, so bringing other friends in on the fun can make the evening even more memorable. If you decide to bring a bigger group, you’ll have time to switch on and off the court and chat with each other in between matches – great for bonding and getting to know one another better. 

And, you have the added benefit of high fives (as Travis Kelce says, the most “electric” thing you can do at an event) when you score a point or hit a great shot. For even more fun, try coming up with team names or offering a friendly wager. Winner buys drinks! 

  1. Eat and Drink  

All that sweat and effort on the court definitely earns you tasty shareable bites afterwards! Enjoy the experience of building something delicious together like going with a couple of fun pizza options, then sampling each others’ favorites. 

Cheers with a crafted cocktail and raise a toast to your date’s best moments on the court – because serving compliments is the best move you can make. 

  1. Keep it Simple. 

The best dates are stress-free. Nobody wants to feel like they’re on a super structured schedule or feel the pressure to be on time for a following dinner reservation. Choose a spot that you can enjoy being together, playing and relaxing for multiple hours. It’s even better if that spot offers entertainment, food and plenty of date night options all in one place, so you can keep conversation and interaction flowing the whole time. 

The best part about a date night at an all-inclusive spot like Pickle Haüs is that your entire date is in one place! Get your game on and share a delicious meal or a few tasty appetizers before snuggling up together with drinks near the cozy firepits. 

  1. Creating a Memory and Finding “Your Place.”  

It might be your first date playing pickleball together but chances are it won’t be your last.  

Whether you get into your groove with a regular double date meetup, sign up for couples’ lessons or even join a league – there are so many ways to keep a regular date night in Chicago on the books week after week. Finding an activity, a space and a community that you both enjoy is the secret to enjoying time together for years to come. 

Ready to come out and play? Book a court and plan your next Chicago date night at Pickle Haus. You bring the date. We’ll help you make the memories!