Our 5-Step Guide to Dating in Chicago
Dating in Chicago is Hard, Follow our 5-Step Guide to help you win.
Every city has its own dating vibe, New York City is fast and forward, Los Angeles is all about how you present, but Chicago is a totally different game. You’re not alone if you struggle to understand the subtle difference between each city but that’s where we can help. Understanding how the game is played is the only way to learn how to play the game to your advantage.
Dear Matty,
We agree, of all of our dating experience across the country Chicago Dating is definitely its own unique blend of weird. But here’s what we’ve learned about our Sweet Home Chicago.
Meeting new people is difficult, many Chicagoans have grown up around the city, went away to school, and moved back with two strong groups of friends, high school and college. These large social networks check so many boxes that it comes off as no new friends. Translate this to dating, and you’re looking at people who are interested in the idea of dating but when it comes down to the execution of meeting a new person, they may or may not show up on the date. Why? Because they could be doing literally anything else with any one of their friends that they already know and in all honesty that could be more fun than your date. It’s a risk vs reward toss-up every time. Harsh but true.
It’s flakey, it’s emotional toying, and it’s not ok. But it’s happening and our guess is that you’re running into for the first time. If you’ve ever been out with someone and have enjoyed their company but then they start to cool off and slowly back out of your life? Yeah, that’s going to happen. How about trying to talk to a stranger on the street, or better yet in a bar. Unfortunately, we haven’t heard as many “we met IRL” stories, lately. So then how do you navigate this dating scene in Chicago? Don’t worry, we broke it down for you.
AND, SIWPE RIGHT’s 5 step approach for Dating in Chicago:
Dating in Chicago Step #1 - Get online
There’s nothing outside of the online dating world in Chicago. If you are lucky to have friends setting you up with their friends and co-workers then enjoy it while it lasts. That is an especially slippery road as sometimes those setup dates don’t work out. For everyone else, it’s easier to meet someone on a dating app and honestly, for about 9 months of the year, everyone hibernates and dates through apps anyways. Pro Tip: Don’t make the mistake of cobbling together your dating profile by yourself. Contact our stylists to consult and craft a new dating profile, we take your dating profile pictures and write your dating profile bio.
Dating in Chicago Step #2 - Must love to eat and drink
If you live in Chicago then you already know that you are the number 1 rated restaurant city in the country. Choosing where to make dinner reservations should be one of the biggest FOMO inducing moments of the week. It’s absolutely a #ChicagoProblem but thankfully we have The Infatuation to guide us through our craziest food dreams as well as our best date night dinner ressie suggestions. More than 90% of the dates that happen in Chicago are centered around food and drink, with all the incredible options in Chicago at your fingertips, get on your phone and start booking date night reservations.
Dating in Chicago Step #3 - Respect tradition
Chicagoans are passionate sports fans, traditionalists, and family-oriented friends. We like our traditions and we like people who want to enjoy them with us. If you’re new to Chicago, join in the celebrations. Hang out with our friends and enjoy our sport traditions. Our love for Chicago gets us out of bed, and it’s our loyalty that keeps us here through the winter. We love going to games and shows, apps like Ticketmaster and GameTime work easily for booking date night plans.
Dating in Chicago Step #4 - Join your office sports team or sign up for a comedy class
We are not promoting the idea of dating within your company, but we do think there’s good value in continually meeting and socializing with new people. It keeps your first date dating skills fresh. Plus, every encounter we have on a first date is improvised. If you have the worst first date nerves sign yourself up for an improv comedy class at The Second City. Trust us, if you follow their program you will find yourself with a new sense of confidence in more areas than you expected. Our Founder/CEO Chloé Miller feels it was one of the best decisions that she made. Plus, she’s still in close contact with her improv troupe, Tequila Hammock.
Dating in Chicago Step #5 - Tune into the music scene
Have you ever heard of Chance the Rapper? He’s proof the Chicago music scene is not to be missed. From great dive bars with live performances like the California Clipper or Kingston Mines, to the first class tour stops at Wrigleyfiled or Soldier Field, Chicago is pulsing with shows all over the city. In the summer, we suggest checking out Lollapalooza, Riot Fest, and Windy City Smokeout for a fun music festival experience dropped in the middle of the city, meaning you can Uber back to your bed at the end of the night - heelloooo!.
There you go Matty, don’t forget to report back. We love hearing from you.
- the AND, SWIPE RIGHT team
What do you think? Did we miss something? We want to hear from you, email us with your thoughts, your feedback, and what topics you want to know more about. Reach us at info@andswiperight.com