Chicago has been the backdrop of many romantic films.  

When Harry literally met Sally, it was in Chicago. Young love blossomed between Ferris and Sloane at Wrigley Field. Julia Roberts’ character almost kisses her best friend days before his wedding on a beautiful, downtown boat tour.

Life isn’t like the movies.

And according to this study, Chicago is one of the worst cities for dating. Like number-133-out-of-150-cities-bad.  

To be fair, Aurora, IL was ranked at number 141.

With February being the month of love and romance, we wanted to find out: Is this really true? Despite what Hollywood has shown us, is Chicago that unlovable when it comes to singles and the dating scene? So, we went to the experts to find out if Chicago can be the backdrop of your next real-life romantic plot. Here’s our Q&A with Anita Chlipala, founder of Relationship Reality 312 therapy practice, and America’s Dating Coach, Patti Feinstein, both based in Chicago.

The Idea Forge: Is Chicago a tough city to find love?

Anita:Yes, because people are looking for ‘someone better’ even though there are only so many eligible singles in a city of this size. If you have problems with someone, it’s easier to think, ‘This wouldn’t be the case with someone else. There’s someone better for me out there.’ Although, I don’t think this just pertains to Chicago, but is a phenomenon seen nationwide.”

Anita Chlipala hosts dating workshops in Chicago throughout the year.  Her next one is in April.

Anita Chlipala hosts dating workshops in Chicago throughout the year. Her next one is in April.

Patti:Chicago is good for dating IF you are from Chicago.  

I think because Chicago is a place where a lot of people come to get their careers off the ground, it’s also a transient city. When you have a transient city, people move and most people from the Midwest, they’ll move here since it’s the biggest city but then they’ll leave and that’s the problem. If it is hard to come here from another city and make friends, then it’s really hard to come here to find love.”

What pros does Chicago have that help us fall in love?

Anita:There are so many opportunities to meet singles. You could probably go out every night of the week with all that Chicago has to offer with networking events, charity events, singles mixers, junior board parties, holiday events (like Valentine’s Day or special bar crawls), sports, food fests, concerts, world-class museums and things don’t have to be expensive! There are free things to do, too.”

patti head shot 2015
Dating coach Patti Feinstein.

What cons does Chicago have that keep us from falling in love?

Patti:The biggest one I can think of —  it is cold! Chicago can be so cold that no one is going outside. In the spring, summer and fall, all of the [sports] leagues are going on and people are walking on the beach with their dogs and are playing volleyball, etc. They are doing things so chance encounters are more frequent. It seems to me that Midwesterners tend to hibernate in the winter when there’s a lack of sunshine and there’s a lack of activity.”

For singles in Chicago, what advice can you give them to not give up hope?

Anita:Give people a chance. Don’t dismiss someone too quickly. I always hear from clients who live in the city, ‘I won’t date people who live in the suburbs.’ But then complain that the people they meet in the city don’t want to settle down. That’s because the singles who are ready to settle down live in the suburbs in their houses! Also with more people dating online and never meeting in person, there’s a block to making connections.  The best way to know if you connect with someone is face-to-face.”

Technology, dating apps, online matching sites – are they helping or hurting relationships?

Anita:For singles, with the growth of dating apps, it can perpetuate the belief that there are so many single people and they’re only a click away, which isn’t necessarily true. Women also wait for the guy to initiate contact online which is a terrible idea because with so many profiles, it’s easy to be missed. Women should definitely reach out if they’re interested. And singles, when you are out and about, put away your phones and take out your earbuds. Technology can be a huge turn-off and make you less approachable.

Patti: I think technology is helping the older people to find long-lasting relationships. We’re talking the 40-plus crowd. This group of people, I believe, have chilled out a little bit, they’re not as uptight and they are willing to put in the work.

So, for all you Chicago singles, don’t pack up and move away in the pursuit of love. Can you find it by Valentine’s Day 2017? Maybe not, says Anita, but it can happen if you make love a priority for 2016, “Dating is work, as I tell my clients. It’s better to put the work in the upfront than to suffer in marriage.”

And Patti says, whether you live in Chicago or Chuathbaluk, Alaska (population: 118), you will find love once you remove your all preconceived notions.  

The people who have been successful in finding love are the people who share the idea of there is no such thing as a good or bad date,” she says. “Love happens when you stay in the moment and have no expectations.”

Remember, this isn’t a movie, but you can start writing your own love story.