The Perfect First Date in Chicago

It’s all romantical and stuff.

First of all, no, I did not go on a first date while in Chicago. Give me a little credit! I’m married! But having said that, Dear Husband and I did do the things mentioned below, and it was all romantical and stuff. So I had to put it out there as a suggestion, because if someone took me on a first date like this back in the day, I’d have been swept off my feet.

Start off the evening with some authentic Chicago deep dish pizza at some intimate little bistro near the city center. Not only is this the ultimate comfort food, but it takes longer than a regular pizza to cook, so you’ll have more time to talk. (Allow for that extra time in your plan, because you don’t want to be late for the next part of the date. Show this person that you put thought into this, and that you’re logistically coordinated.)

For our deep dish experience, we went to Pizano’s Pizza on Madison Street, right near the Loop. Is it the best pizza Chicago has to offer? I have no clue. But we thought it was fantastic. I’d definitely go there again if given the chance. (Shoot. Now I’m craving deep dish pizza.) Wherever you decide to dine, if they take reservations, make them, because there’s nothing worse than craving something, and showing up only to discover there’s no room or there will be a long wait.

Assuming everything went well on the date so far, you’ve gotten a chance to get to know each other better (because you’ve shown interest by asking questions, of course), and you’ve indulged in comfort food. Your bellies should be all warm and content by now. Let’s assume the ice is officially broken.

Now it’s time to go to phase two of this date. Head over to the Chicago Riverwalk Jetty, between Wells and Franklin Streets. We were able to hop on the Loop and we got there in no time. (I have to say, public transportation is abundant and convenient in Chicago. We took advantage of it every chance we got. We didn’t even bother getting a rental car for this portion of the trip. No need. That, and parking is expensive.)

The Riverwalk is romantic in and of itself, and if you arrive there early, you can take a stroll. But the block I mentioned above is where the magic happens, every evening, 9 months out of the year.

I’m talking about Art on the Mart. This is a vibrant, moving, colorful digital art display that is projected on the 2.5 acre façade of The Mart, which is the building directly across the river from you. Stake out a seat on the benches in this area, or stand if it’s a more heavily attended evening, and you’ll be perfectly positioned to hear the music that is coming from the permanently installed speakers behind you. That music is part of the experience, and it is synchronized with the moving images.

Art on the Mart occurs nightly, 9 months out of the year. And it’s free. You can’t beat that price!

The start times vary with the season, because, of course, the display is best viewed after dark. Check the Art on the Mart website to verify the time before you go, because if you show up late, you might miss something good. This year, the schedule was April 14th through June 7th, 8:30pm to 9:30pm; June 8th to September 13th, 9pm to 10pm; and September 14th through December 30th, 7:30pm to 8:30pm.

If you want to impress your date, you can hit them with some fun facts about Art on the Mart. For example:

  • Through the magic of digital mapping, none of the laser projections shine in any of the building’s 4,262 windows. (I found that fascinating, and I’m sure it’s a huge relief to any employees or visitors who happen to be in the building’s offices, design showrooms, restaurants or retail facilities .)
  • The “palette” used to create and display this art is the size of about 2 American football fields.
  • Art on the Mart hosts the work of a diverse range of artists, and these artists are changed periodically, so you can enjoy different displays if you visit several times throughout the year.
  • The project’s goals are to provide public access to innovative contemporary art for Chicago residents and visitors alike, and to inspire positive community engagement along the river.

While we were there, the artists featured were Yiyun Kang and Charles Atlas. Sadly, that show will be over by the time you read this. Check out some of the videos Dear Husband made, below. And if you are unable to see those, I’ll throw in a few still images, although they really don’t do the work justice. But there’s always the Art in the Mart website, and the beauty of that is that you can see the work of past artists online, from the comfort of your own home, so check it out.

The reason I believe that this would be the perfect first date is that the night will still be young when the event wraps up, and if the date went badly, you can go your separate ways and still have time to chill out before climbing into your lonely bed. But if the date goes well, you will still have time to have more fun with the person you chose to spend the evening with. And in a city like Chicago, the possibilities are endless.

Check it out, y’all. I wrote a book! http://amzn.to/2mlPVh5