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“Matchmaker, matchmaker…”

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Chicago Jewish cupids help their friends find love 


Tracey and Todd tying the knot
Photo credit: Artisan Events, Inc.

Happily ever after

Once upon a time in a land called Chicago, a mutual friend fixed Brooke and Sean up on a blind date. While the two did not fall in love, they became dear friends. Years later, Brooke fixed Sean up with a woman named Cynthia. They fell in love and married. Meanwhile, Brooke met another man named Mike. They, too, fell in love and got married this past summer. And, everyone lived happily ever after.

A Needle in a Haystack

There’s an old Jewish saying that ever since creating the world, God has been making matches, a task more difficult than parting the Red Sea. Every so often special people – like Brooke Mandrea from the story above – assist in the tough task of matchmaking. Brooke is one of the special people who excel at helping singles find their happily-ever-after. She is not a professional matchmaker; she’s simply a champion of love who strives to help others find their shiduchs (matches) out of the goodness of her heart. “It’s considered a great act of chesed, or kindness,” said Rabbi Asher Lopatin, spiritual leader of Anshe Sholom B’nai Israel Congregation in Lakeview. “One of the ultimate acts of kindness is to try to find people someone who will love them and give them companionship.”

In her years of matchmaking, Brooke, who lives in Wicker Park, has set up a whopping seven marriages and even more unmarried couples. Finding one’s match, according to Brooke, is like “finding a needle in a haystack, and if I’m able to be that connection, it’s a mitzvah.” When matching couples, she searches for a meaningful connection between two people. “I never do it where it’s like, ‘Oh, she has a pulse and he has a pulse…” she said. “There has to be something more than they both like line dancing. There have to be shared values, morals or world outlooks.”

She sometimes brainstorms couples in the swimming pool. While she’s swimming laps she’ll envision two people that just seem meant to be, such as Cynthia and Sean Pierce, of West Lakeview, who have been married for three years. Brooke, herself, had been fixed up with Sean on a blind date many years ago. Then, Brooke and Cynthia met years later while volunteering at the Jewish United Fund’s Uptown Cafe.


The happy couple, Cynthia and Sean

“I thought, ‘Oh my God, this is Sean’s other half,’” Brooke said. When she approached Sean about the fix-up, his initial response was, “Not interested.” He was wary because Brooke had set him up on a couple of failed blind dates in the past. Yet, the matchmaker persevered. “I called him repeatedly,” Brooke said, “and told him that the only way to get me to shut up is to go out with her once.”

Six months later, Brooke pointed them out to each other at a music program one Friday night at their synagogue, but there was one catch. Cynthia was on a date with someone else. ‘Sean, I want you to meet her,’ Brooke told him. ‘She’s on a date, but who cares about that?’ The following month – with Cynthia’s date no longer in the picture – Brooke introduced Sean to her at synagogue. On their first date, Cynthia and Sean had a lively political discussion over sushi. In November of 2005, they married, and Brooke signed the ketubah (marriage contract) at their wedding.


Cynthia and Sean on their wedding day
Photo credit: Jason Lazarus


Matchmaker and friend Brooke signing the ketubah at Cynthia and Sean’s wedding

Brooke comes from a family of matchmakers. Her sister, Allison Leviton, has tied Brooke, with seven marriages to her credit. Their mother, Joyce Leviton Asher, passed down to them the shiduch talent because she has set up, as she puts it, “too many couples to count.”

Brooke tries to fix up couples that otherwise would be unlikely to cross paths. She has paired a woman who teaches in the northern suburbs with a downtown trader as well as a couple in their 70s who both frequented the Lyric Opera, but on separate days, and who both audited classes at Northwestern University, but on different campuses. “When else would these couples have met?” Brooke asked.

Todd Fine wondered how he would have met his bride, Tracey Fine, if not for their friend Jennifer Elvey, because he didn’t frequent Jewish social events as Tracey did. Jennifer, of Wilmette, had been trying to introduce her friend Todd, from her gym, to her close friend Tracey for a while. Jennifer had thought the two might hit it off because – among other similarities – they shared a common interest in martial arts and had similar, low-key socializing styles. In 2005, Jennifer attended the Young Leadership Division’s Purim Party at a Chicago nightclub with Tracey, hoping that Todd might attend the party too. She didn’t tell Tracey or Todd that the other might be there, because she wasn’t sure that Todd would come and she didn’t want to make them nervous.

Sure enough, he was there that night and Jennifer introduced them. “I still remember the spark between them. It was amazing,” Jennifer said. Tracey and Todd talked throughout the evening and, at the end of the party, Todd offered Tracey a ride home. “I typically would never accept a ride home from a guy that I met at a bar,” said Tracey. “I literally was like, ‘Are you sure you’re not a murderer?’ Because he was Jen’s friend though, I considered it.”

On their first date, Todd picked Nacional 27 because he knew that Tracey loved Latin food and music. “We made our best attempts to salsa dance together, but we weren’t very good,” Tracey said. Their clumsy dancing didn’t hamper their relationship though. In fact, the couple married in June of 2007. They were so grateful to Jennifer that, at the wedding, Jennifer signed their ketubah. Tracey and Todd, who live in Wicker Park, are expecting twins in March.

Jennifer fixed up a second Chicago Jewish couple, who married in November. “I definitely think that two of the best things I’ve done in my whole life have been introducing these people to each other,” said Jennifer, who herself will stroll down the aisle in June. “It’s just a great feeling to sit at these people’s weddings and know that I played a small role in it.”

Although singles in the religious Jewish community often rely on professional matchmaking, Debbie Wengrow, a West Rogers Park religious Jew, strives to match people in her spare time – and isn’t paid for it. Debbie meets with a group of approximately 10 religious Jewish women on a monthly basis to brainstorm potential mates. Through word of mouth, they gather names of religious Jewish singles looking to be set up. They interview candidates and match people according to religiosity and personality. “[Matchmaking] is not up to us – God has a plan, but we still need people to try to help out,” she said. In four years, Debbie has set up four married couples; the entire group of women is responsible for some 10 marriages to date. They offer their service for free, and similar groups meet in cities throughout the country.

Making Room at the Shabbat Table

In the traditional way of matchmaking, a third party sets two single people up to meet a blind date to see if the sparks fly. Another way to match people is to arrange social gatherings for a bunch of friends and – with a little luck and beshert (destiny) – who knows which pairs might emerge? Michelle Lawner Whitesman has introduced more than five couples in her hometown of Kansas City and in her adopted home of Chicago. Dating back to her sweet sixteen in Kansas, couples have been meeting one another at her parties. Three years ago, she introduced a couple at her March Madness get-together.

In an age of impersonal internet dating, what’s the harm in a set-up by a friend? asks Michelle. “It makes it more personal when a friend who knows you well thinks of people for you,” she said. “The more people you have looking for someone for you, the greater the chance you have of meeting the right person.”


Michelle Lawner Whitesman and Jennifer Elvey, close friends, act as matchmakers for their friends

Michelle found her own match – Louie – whom she married in November. Their union has energized them to help their friends find love. “When you’re happy, you want those around you to find love and be happy,” she said. “My husband also set up a couple who married last year. He has taken on looking for matches for our friends too. Now it’s like a tag team effort.”

Michelle and Louie frequently invite their friends for Shabbat dinner at their new home in downtown Chicago. While their motivation for Shabbat is about forging community and celebrating a Jewish ritual, if two of their friends should happen to meet, that would be the icing on the cake.

Another popular Shabbat dinner table in the city is at the Lakeview home of Rabbi Lopatin and his wife, Rachel Tessler Lopatin. They, too, invite people, often singles, to their home just about every Friday night as a way to share Shabbat and build community – and perhaps create some love stories along the way. “Sometimes, people meet at our table and then meet again at a Federation event or shul or running in the park and say, ‘Oh, I met you at the Lopatins,’” said Rachel, who also does matchmaking for the Jewish singles site “Saw You at Sinai.” “We try to widen the pool for people to meet each other. I don’t know that we have any great insight as to who would be good for whom, but it’s more that we hope [to increase the odds] that people can meet each other.”

As far as she knows, three marriages have resulted from introductions at their Shabbat table, plus Rachel introduced another couple at synagogue. Rachel sometimes wakes up in the middle of the night thinking about a potential pairing. Her thought process focuses on personality, observance level and future goals. “I’m motivated by this mitzvah,” she said. “It’s painful to hear that people want something and are having a hard time getting that. If I can be helpful in that, I want to be.”

Six Degrees

And in the game of Jewish six degrees – or fewer – of separation that makes this story come full circle, Rachel was the matchmaker who fixed up Brooke on that date with Sean, who later married Brooke’s friend Cynthia. “If it hadn’t been for Rachel introducing Sean to Brooke,” Cynthia said, “then the two of us wouldn’t be together.”

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