Best Dating and Relationship Experts in Chicago

Best Dating and Relationship Experts in Chicago

Posted By: Kelly Seal Date: 08-16-2019 Comments: 0

In our new series, we’ve shared our choices for the best of the best experts in dating and relationships on both coasts – specifically L.A. and New York. Now, we’re heading to the Midwest, and our next stop is Chicago!

This is a bustling, exciting place for young single professionals, with a lot of options for cool places to meet. (Some people even report finding love on the “L” – an elevated train line that runs downtown). Similar to L.A. however, people don’t like venturing outside of their neighborhoods because of the time it takes to get around on public transit, and they don’t often like going out in bad, windy weather which let’s face it – happens a lot in Chicago. So “cuffing season” is pretty real here in the winter months, but people tend to be more social and have more flings in the summer when the weather heats up.  

As we head into fall, the dating cycle will change again, and people will start to couple up. So why not get serious about your love life now? (Hint: The end of summer is a great time to get a matchmaker, Chicago singles!)  

The city doesn’t disappoint when it comes to matchmaking experts and dating coaches. There are plenty around, but we’ve pulled the best of the best for you – so check them out and see if they’re a match for you! 

Love and Tony McPherson

The powerhouse founders of Love Infinity have been married 35 years and offer up healthy relationship guidance to singles and couples. Frequent guests on local and national TV and radio, Love has an extensive background as a mental health professional and Tony as a clinician with DCFS, as well as an advocate for inner city youth. They have guided people through pain and trauma and taught them how to rebuild trust, how to listen and communicate with each other, and heal from old wounds to move forward into healthy relationships. Incredibly inspiring, they offer private coaching and group events. 

Bela Gandhi 

Bela is the founder of Smart Dating Academy and has been matchmaking and coaching singles for twenty years. She has a team of love experts, but she is at the center of her brand. Steve Harvey has referred to her as “the fairy godmother of dating” thanks to her intuition about people and relationships. Her team offers both remote coaching and a “VIP service” where you meet with a stylist for a photo shoot and create a new online profile in addition to follow-up coaching sessions. Prices aren’t cheap, but they do offer discounts for certain sessions.

Barbie Adler

Her tagline is “finders of keepers.” Barbie is the founder of Selective Search, a “luxury matchmaking company” that uses Fortune 500 executive recruiting techniques to help professional men and women connect. If you are serious about love, you might want to check them out since they have an 87 percent success rate (and have been touted by The Wall Street Journal). But be prepared to work! There’s a six-step process to getting matched which includes in-person evaluations, so it’s important to put your best foot forward – as you would a job search.  

Stefanie Safron 

Founder of matchmaking and coaching service Stef and the City, Stefanie Safron has been dubbed “Chicago’s Introductionista.” She’s been matchmaking for fifteen years, starting out as a contestant coordinator on “The Dating Game” and moving on to work for some top matchmaking companies in the nation. She committed to “innovating the industry” when she noticed what wasn’t being done right, and soon ventured out on her own. She’s the ultimate networker and prides herself on being able to connect the right people face to face—her tagline is “revitalize your social life.” 

Jason Silver

Jason Silver has been dishing out dating advice for ten years, specifically geared toward “ambitious women” who have great careers but not enough success in the dating department. His main focus is on personal transformation, based on his own experience growing up and learning to overcome his own struggles with his weight and meeting women. “”I learned that [meeting the right person] is not just about interests, but about values.” He brings his spiritual awareness into every coaching session to help people not only find the right relationships, but also be the best version of themselves.  

Chicago singles, with these great coaches and experts, what are you waiting for?

Kelly Seal is a freelance writer, dating expert, and author of the book “Date Expectations: A Guide to Changing Your Dating Life and Finding Real Love.” She got her start in the dating industry by hosting speed dating events around southern California and offering advice and encouragement to attendees. She now lives in L.A. and spends her free time hiking in the Santa Monica mountains and blogging at