Chicago Matchmaker



Chicago singles have been turning to our professional matchmakers to find them love for years. If you live in places like Near North Side, Near South Side, Lincoln Park, Lakeview, Andersonville, Kenwood, Hyde Park, or Rogers Park it might be hard to meet your match while you’re out and about.

The suburbs of Chicago are hot pockets for singles, but randomly meeting them is hard to do. Bridgeview, Lisle, Northlake, Summit, Midlothian, Matteson, Worth, West Chicago, Crete and Mokena are the top ten suburbs for singles in the greater Chicago area. 

Although it might be hard to meet someone in the Windy City there’s no shortage of outstanding singles. Each of our clients are evaluated based on strict criteria. We conduct criminal background checks and meet everyone we represent face-to-face. We do all that we can to ensure that our clients have a safe and worry-free experience.

To find love in the Windy Cindy complete our Get Started form or call us toll free at (800) 734-9230 



keyGet Started


Dating can be tough. With guaranteed matches and date feedback we do whatever it takes to guide you into a relationship.

Complete our Get Started form and you will be contacted to discuss your matchmaking and coaching options.

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 How It Works


Online dating is difficult. We guarantee matches that meet your criteria. Your personal coach will communicate feedback, troubleshoot issues and guide you into a relationship.

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About Us


Joann Ward has over 30 years of experience in the dating service industry. Along with her son, CEO Steve Ward they became internationally known as the Hosts and Executive Producers of VH1 Tough Love

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Check out the latest updates below.


The Simple Secret To Getting 5x More Matches On Dating Apps

Saturday, April 22, 2017 - 3:53 PM

The Simple Secret To Getting 5x More Matches On Dating Apps
While 38 percent of American singles use an online dating app or site to search for dates, a striking one-third of them never actually meet anyone face-to-face. The most common reason cited is the fear of not knowing who will actually be sitting on the other side of the table. Continue Reading


Why is everyone breaking up? It's the annual 'spring clean'

Wednesday, March 29, 2017 - 1:31 PM

Why is everyone breaking up? It's the annual 'spring clean'
The likelihood of divorce climbs in January and February, peaking in March, according to an analysis of Washington state divorce filings published by University of Washington researchers. And breakups, according to Facebook data analysts, tend to spike in the spring and again in the summer -- perhaps the natural counterpoint to the phenomenon known as cuffing season, when singles suddenly settle down. It's a cycle that appears to accelerate in February, a month that happens to include Valentine's Day. Continue Reading


You're Never Going to Be Happily Married, Unless...

Tuesday, March 14, 2017 - 9:49 AM

You're Never Going to Be Happily Married, Unless...
As a matchmaker and dating coach, I classify people into one of two categories. They're either relationship oriented or not. Many people, men and women alike, truly believe they are fit for a relationship. They think they have everything going for them. They're healthy emotionally, physically, spiritually and financially. They want to have a traditional, nuclear family in a two parent household where both of them can grow as individuals and together as one. But there is one key difference between the relationship oriented people out there, and everyone else. Continue Reading


Why Marriage Minded Women Outnumber Marriage Minded Men

Saturday, March 11, 2017 - 6:32 PM

Why Marriage Minded Women Outnumber Marriage Minded Men
I’m hard pressed to find anyone who will disagree that there is a gap between the number of marriage minded women in the US and the number of marriage minded men. But that gap is widening, and widening at an accelerating rate. Here’s why. Continue Reading


Dating trends of Chicago universities analyzed. Do students agree?

Monday, December 05, 2016 - 2:37 AM

Dating trends of Chicago universities analyzed. Do students agree?
Would you believe University of Chicago singles are the most chatty? The hottest singles attend Northwestern? Or that the least assertive daters go to DePaul? They're all true, according to a user analysis by dating app Coffee Meets Bagel, which also looked at Loyola and the University of Illinois at Chicago. Continue Reading

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