Chicago Matchmaker



Our professional matchmakers have been matchmaking Chicagoland singles looking for love since 2009. If you live in places like Near North Side, Near South Side, Lincoln Park, Lakeview, Andersonville, Kenwood, Hyde Park, or Rogers Park its hard to meet your match while you’re just out and about.

Chicago singles beyond the city in places like Bridgeview, Lisle, Northlake, Summit, Midlothian, Matteson, Worth, West Chicago, Crete and Mokena have hired our professional matchmakers and personal coaches to meet the man or woman of their dreams.

Although it might be hard to sometimes to make it out and about in the Windy City there’s no shortage of outstanding singles surrounding you. Online and mobile dating often do more harm than good because they tend to be flooded with bad actors. We prove identity and age, run criminal background checks and personally interview people we represent face-to-face to ensure our clients have a safe and worry-free experience.

Complete our Get Started form or call us toll free at (800) 734-9230 for matchmaking services in Chicago. 



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 and dedicated matchmakers will communicate feedback, troubleshoot issues and guide you into a relationship.

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Heartcoach About Us


Joann Ward has been matchmaking for over 30 years. Her son, Steve Ward followed in her footsteps in 2003. They became internationally known matchmakers as Hosts and Executive Producers of VH1 Tough Love

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Here's How to Suck It Up and Ask Out Your Crush

Tuesday, February 20, 2018


Here's How to Suck It Up and Ask Out Your Crush
Plus first date ideas!

by Marni Eth


Whether you are nursing a breakup or have been single for a while, there is never a bad time to work up the courage to ask out a crush! According to the CEO of Master Matchmakers, Steven Ward, there is nothing wrong with asking out a stranger who has caught your eye. Ward is an expert on love, dating and relationships, whose services also includes coaching. 

Not sure that you are crushing someone? It doesn't have to be someone you know well, he or she could be a coffee shop regular who you are curious about, someone you are always in the elevator with at work or a gym regular on your same schedule. 

Once you establish who you want to go for, the hardest part is that you probably don’t know much about him or her. Even if your crush isn’t wearing a wedding ring, he or she still might be committed. This is why Ward encourages the casual approach for these scenarios: "If you try to cram too much into the ask, you could ruin a perfectly good opportunity."

Here are a few openings that Ward suggests: 
  • I see you here from time-to-time and my curiosity is killing me. You wouldn’t happen to be single by any chance, would you?
  • Each time I run into you I wonder what your deal is. Would you like to grab a drink or bite to eat sometime?
  • I can’t tell if you’re seeing someone, so I just thought I’d ask if you’d like to go out sometime and get to know each other a little better.
If you only know your crush through social media, the same concept works for sliding into the DMs. It’s not creepy if it is something so casual and to the point. If they are interested and single, go for it! 

So what kind of date do you pick when you don’t know him or her so well? "The goal is to be able to chat and get to know each other better. You don’t want to be too distracted doing an activity that could drag out longer than either of you would like." Depending on your preference, keeping the date a quick bite is completely acceptable. 

Ward approves of first dates getting coffee, yogurt, ice cream, cocktails, or meeting for happy hour. If you know your crush likes being active, Ward suggests a walk through a promenade, along a boardwalk, through a street festival, park, or museum. If you are feeling in the mood for a romantic dinner, one of Ward’s top suggestions is picking a spot that is "a well-reviewed, locally renowned restaurant." No matter which option you choose, "just putting thought into where you’re taking someone shows you care."

If all else fails, there is no shame in the matchmaker game. Ward and his team cater to upscale, eligible men and women who don’t like approaching strangers or meeting random people online. 

P.S. It’s real-life confession time! Watch Bravo’s new digital series, Secret Crush, to see what happens when real people reveal their secret crushes — will they fall in love … or fall flat on their faces?

Personal Space is Bravo's home for all things "relationships," from romance to friendships to family to co-workers. Ready for a commitment? Then Like us on Facebook to stay connected to our daily updates.

 

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