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Lara Shiffman is the most successful Chicago matchmaker you can’t hire.  With dozens of relationships, five marriages and eleven (11!) babies to her credit, Shiffman’s matches are the stuff of legend, fairy tale – or at least a very profitable business.  The irony?  She’s not even a professional.

“My whole life I’ve introduced people, both in business and socially,” says the irrepressible blonde, who runs the strategic consulting firm JKLS PR, with her business partner, Jill Katz (who met her husband through Shiffman). “I do this out of love for my friends, not as a career or for any type of compensation.  I just want my friends to be happy.”

With marquee clients like Barneys New York, Sprinkles Cupcakes, Public Hotel, The Pump Room and W Hotels Chicago, Shiffman has built a thriving business on her uncannily instinctive feel for effective partnerships, both professional and personal. “We bring together like-minded brands all the time that can benefit from cross marketing opportunities, which is exactly what I try to do when I introduce two people I know and love.”

Luckily for them, Shiffman knows and loves a lot of people – she’s a vertiable Gladwell-esque “connector.” Her friends and clients adore her and universally describe her as a sweetheart. “She knows EVERYONE in Chicago” raves one friend.

Cori McFadden, Lara Shiffman and Spiro Tsaparas

“She obviously possess a gift for seeing how two people may be a match. She’s got ‘it’,” says happily matched entrepreneur Spiro Tsaparas, who lives on the Gold Coast with his girlfriend, Corri McFadden, owner of Edrop-off and star of the VH1 reality show House of Consignment.

Tsaparas met Shiffman through a mutual friend while looking for a firm to organize an event.  “I didn’t know at the time that included in the package was a girlfriend,” the construction company CEO jokes.  “At the end of our first meeting she asked me if I was seeing anyone. I said, ‘No, I am single!’ and she said, ‘We have to do something about that!’”

Later on, Shiffman invited him to a party, promising that she had someone special for him to meet.

“Lara grabbed my arm and said, ‘Come with me! I want to introduce you to someone amazing!’ and from that point on Corri and I have been together,” says Tsaparas. “The chemistry was apparent after a few dates; We moved in together just a few months after we met. That was three years ago!”

“To make the perfect match, you need to be a good listener and have a great understanding of what someone is truly looking for in life, a relationship and love,” Shiffman explains.  Her gift, she says, is a “gut feel.”

She doesn’t believe that opposites attract (“similar goals in life are the key to creating and cementing a relationship”), and “people who make the best matches are the ones who truly know themselves and know what it means to be happy.”

“My rationale,” says Shiffman, “is that if I enjoy the company of two individuals, they will probably like each other as well!”

Intriguingly, none of the couples actually asked Shiffman to set them up, and (perhaps unlike “professional” matchmaking), many commented on how “natural” it felt. “That’s what she does with such ease, not just with me, but with others she has ‘matched’ as well,” says Katz.

Shiffman is obviously special.  “It is her innate ability to truly have a sense for the type of person that would be a good match for one another,” says Katz. “I think it’s a gift and she shares it with people she cares about.”

“I love that I’ve been able to make people happy in their lives,” says Shiffman. “Marriage and family are truly the most important things to me. There is nothing better than a loving husband and great kids.”

Shiffman has been the guest of honor at all five weddings she made possible. “Lara even signed the Ketubah [the Jewish marriage license] at our wedding,” writes Katz in an email.

As for Tsaparas and McFadden? The couple is “talking marriage,” and Tsaparas says “Corri has already started buying kids clothes … I must say that I am very excited!”

Will Shiffman be invited to his wedding – which would make her sixth?

“Of course! Lara will be there!”

This article was published in the Feb 2012 issue of Michigan Avenue Magazine

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