For countless Chicagoans in the last few decades, the classifieds section of the Chicago Reader was life-changing. Especially in the pre-Internet age, it was the place to go for finding a job, finding an apartment, and finding love. The streams of Seeking ads and Missed Connections set the stage for early platforms like and even the dating apps we use today. There is no shortage of couples nowadays who met on Hinge or Bumble, but a few years ago, it was much more common to meet couples who found each other in the dizzyingly packed print pages of the Reader. I currently manage the recently revived Matches section, and it’s not too late to submit an ad and have a love affair of your own. But in the interest of Reader history, I spent the last few months tracking down some of the success stories, so that we can all celebrate the city’s best 50-year-old matchmaker.

Sally Gilbertson and Brent Carter

Sally Gilbertson fondly remembers trekking into the city from her hometown of Wheaton to pick up a copy of the Reader whenever she could. After graduating from veterinary school in June 2008, she moved to the Gold Coast and tried her hand at dating in the city. Sally used and other online services, but her love of the Reader drew her back to the Men Seeking Women section of Matches. 

“I was immediately drawn to Brent’s ad!” Sally recalls. “The Reader was just starting an online site, and when you signed up they put your ad in the paper for a week. The fee was, I think, $1 to join the Reader Online Dating Classifieds, and I signed up right away to meet this guy. There was a profile you filled out that gave a snapshot of some likes and dislikes—you got to see these once you signed up for online dating. One question was, ‘If you have a pet, it better not be . . .’ to which Brent replied, ‘a Republican.’ I thought that was hilarious and was borderline obsessed with meeting him after that.”

Brent’s Matches ad from March 4, 2010

The pair had a lengthy first date in March 2010 at the Old Town Ale House, and things only got better from there. They moved in together later that year, bonded by their love for Chicago’s food and music scenes. Despite “unfortunately” moving to Saint Charles in 2012 for a job opportunity, Sally and Brent come back whenever possible, especially to teach their eight-year-old to love the city, too.

March 13, 2020, marked the tenth anniversary of their first date. Excited at the prospect of getting married on a Friday the 13th, they decided to plan a courthouse wedding—it was the very last wedding at the Kane County courthouse before the COVID-19 shutdown.

“Now that we have been vaccinated for COVID, we continue to enjoy the city. We love taking the train into the city for a night out—especially for pork skins at the Publican and then on to the Emporium for pinball. In May we went to a White Sox game on the first full-capacity night!”

Roy Schuster and Mary Chris Jaklevic

On August 19, 1994, Ukrainian Village resident Roy Schuster placed a Matches ad. Just three weeks later, on September 9, Mary Chris Jaklevic of Lakeview, newly transplanted from Florida, placed a Matches ad of her own. Each wrote a snail mail response to the other’s ad, and it felt like there was a little bit of fate at play.

Both Matches ads from 1994

The pair enjoyed a first date at P.S. Bangkok on Clark Street and nine months later were engaged in London. After living together for spells in Edgewater, out to Dallas, and back to Lakeview, they now reside in Oak Park with two kids and two dogs. As the Reader celebrates its 50th anniversary, Roy and Mary Chris celebrate their 25th.

Sheri and Josh shortly after they met
A recent photo of the couple

Sheri and Josh Flanders

You can read about the Flanders in “We found love in a Matches place,” a short article from 2020. But since Sheri and Josh met through the Reader and today are both freelancers for the paper, they’re part of the family and we couldn’t resist once again writing about this “full-circle Reader romance,” as Josh called it.

Before she placed a Matches ad, Sheri Flanders was Wicker Park resident Sheri Allender. Around the end of 2005, she placed a Matches ad—one that she doesn’t quite remember, except for the fact that she mentioned an Ayn Rand book in her profile. (Unfortunately, this author tried and failed to track it down.) Rand became a topic of conversation on Sheri’s first date with Josh Flanders; the pair met up to see Lynne Jordan and the Shivers, “a legendary Chicago band,” and it was smooth sailing from there. Sheri moved into Josh’s Evanston apartment, and after spending a few years living in Miami, the couple is back and currently calls Rogers Park home.

An ad Liz placed in 2003

Liz Thomson

A key printed in the Reader to explain the many abbreviations found in Matches ads

Minnesota resident Liz Thomson spent nearly 25 years living in Rogers Park, and they were an avid Matches user from 1996 to 2004. As someone who identifies as bi/queer, Liz remembers being disappointed that they had to choose a category within Matches, but they still loved using the Reader to find dates.

“It seemed like a fun and safe way to meet people. I liked that I had control of who I responded to. I always picked up the Reader on Thursdays . . . I figured that if I liked and read the Reader, then maybe I’d find a potential partner or date who also read it. We could always talk about the Reader, if nothing else.”

For nearly all of their Reader dates, Liz took people to the same Vietnamese restaurant in Uptown. (“It was low-key and inexpensive, since I wasn’t always sure if the other person would pay for me, too.”) Eventually, they found someone who shared their love of Chicago’s arts and culture, and “yes . . . he could tell the difference between Chinese, Korean, Vietnamese, and Japanese. It was very important for me to be with a person who understood that all Asian ethnicities were unique and heterogeneous.” The couple were married for nearly ten years before divorcing, but Liz still fondly remembers the small wedding at the former Hot House in the South Loop, surrounded by contemporary art, friends, and family.

Sheila Quirke and Jeremy Hornik

“On New Year’s Eve, 1995, a guy I was dating invited me to the party he was hosting and I thought I was going as his date. Turns out, he had been dating a few other women, too, and we were all invited! Nope. Wrote the ad soon after,” Sheila Quirke remembers. In her search to find a more committed, monogamous relationship, Sheila turned to the Reader in early 1996. Although her Matches ad—which won Ad of the Week (a regular feature that granted the winner a dozen roses)—garnered many responses, she never followed up with any of the men.

“So that is the text of the ad. I am definitely cringing reading my 1996 ad in 2021. My physical stats?! Yikes! That was the norm back in the day. Shudder.” —Sheila

That April, a friend invited Sheila to an improv show at Cafe Voltaire on Clark Street (now closed). She remembered that one of the men who responded to her ad had said he did improv at the same theater. (“Could it be the darling, funny boy in the pink pants? COULD IT?”) Sheila was too shy to introduce herself in person, but she went home and immediately dug through her notebook where she had recorded the contact information and details about the men who replied to her ad. Sure enough, it had to be Jeremy Hornik who she’d seen that night. She left him a voicemail to see if there was any chance he remembered her and wanted to meet up.

“He called the next day and left a message asking if I was the blonde in the front row he had been vibing with,” Sheila writes. “I was, in fact, the brunette all the way in the back. HA!” 

The pair met for coffee, hit it off, and stayed connected even as Jeremy moved to Amsterdam for six months shortly after. Through consistent e-mails (which they still have printed in a binder) and Sheila’s “awkward, but so lovely” trip to see Jeremy in the Netherlands, they solidified their relationship and moved in together in Ukrainian Village once Jeremy returned to Chicago, and they later settled in West Ridge.

Sheila and Jeremy got married in 2001 and had three kids together, the oldest of which they lost in 2009 from a brain tumor. In 2013, they were looking to adopt, and even got featured in the Reader as “This Week’s Chicagoans.”

B and M

In March 1996, two of B’s friends were trying to convince him to let them place a Matches ad in his name. Frustrated with the dating pool, he begrudgingly agreed, with the caveat that they had to work the word “pterodactyl” into the ad text somehow.

“It was a strange and dorky ad to say the least,” B notes.

However, not only did this keyword make it easier to find the ad amidst the pages and pages of Men Seeking Women ads, but it also worked for B to find love. M was seeing someone else at the time, but they didn’t want to go see Ministry play at the Aragon. She responded to B’s Matches ad, hoping to find a date—and a ride—to the show.

The ad placed by B’s friends in 1996

“I tease her that if she hadn’t needed someone with a car that night, we’d have never met,” B jokes. “Apparently she was also high on NyQuil the night she responded, so that might have had something to do with it.”

 But M liked the dorkiness of the Matches ad and the sound of B’s voice on the outgoing phone message, so she gave him a shot.

 “After we had dinner and went to the club, she realized she had left the tickets at home and we had to go back to get them. Should have been a warning sign of things to come! . . . Anyway, it’s now, um, 25 years later (?!) and we’re still together.”

 B and M got married in 2007 and currently live in Portland, Oregon.

Laura Molzahn and Eric Futran

By the time Old Town resident Laura Molzahn placed a Matches ad in July 2000, she was already well acquainted with the Reader.

“I’d been working at the Reader as an editor and freelance writer for nearly 15 years, and before that (late 70s, early 80s) as a display ad salesperson for three years,” Laura remembers. “The Reader’s original owners had gone to the same college as my first husband and me; he’d started delivering papers on the Northwestern campus in early 1971. Then I started helping him and we graduated to Lincoln Avenue stores, where we heard ‘Hot off the presses!’ about a jillion times each Friday. We made $8 a week.”

Laura, whose first husband passed in 1997, attributes being 50 and having a daughter as to why she didn’t receive a lot of replies to her Matches ad. “All were by voicemail back then. I only responded to one: Eric’s.”

Laura’s Matches ad from 2000

Eric Futran was a widower himself, living in Roscoe Village with his 11-year-old daughter and ten-year-old son. It turned out that he also had a connection to the early days of the Reader, as a photographer with some award-winning front-page shots. The pair likely even crossed paths at some Reader events before going on their first date on Armitage, at a bar near the Old Town School.

“Eric impressed me for three reasons: One, when I mentioned I was hungry, he immediately ordered an app. Two, he told me he’d taken a second shower that day in honor of meeting me. Three, he didn’t ask any intense personal questions, despite our shared widowhood.”

Merging to become a family of five, Laura and Eric got married in 2002, with plenty of Reader friends in attendance.

Kimberly Rachal and David Chase

In early 1994, Lincoln Park resident David Chase put an ad in the Reader classifieds. He was a leasing agent at the time, looking to rent out an art gallery space in River North on a ten-year lease.

David’s classified ad from 1994

Kimberly Rachal, an artist who lived in Edgewater, was seeking more of a temporary art space, one where she could create a two-week show for her art glass—sort of an early version of a pop-up gallery.

She replied to David’s Reader ad and met him for a tour. Kimberly tells me, “I was immediately attracted to him. He was very handsome, very well-dressed.”

David must have felt the spark, too, because he completely disregarded the notion of a ten-year lease and rented to Kimberly. For the two weeks that she worked in the gallery space, she noticed David every time he made his way to and from his upstairs office. “There goes David Chase!” she’d cheekily say to her business partner Nick. She could sense the mutual attraction.

At 5 PM on the last Friday of her exhibit, David walked into the gallery. According to Kimberly, it went a little something like this:

Watch this . . .” she muttered to Nick, before confidently addressing David. “David Chase! Are you here to take me to dinner?”

David: “I am! Are you ready?”

Kimberly: “I am!” She had no idea that David had spent the entire two weeks working up the nerve to ask her out.

They’ve been together ever since, as life partners and business partners. Kimberly and David got married on October 5, 1996—which means they’re another couple celebrating their silver anniversary this month—at the Church of the Epiphany in West Loop. In 2011, that church closed, and Kimberly and David bought the building in 2017 to convert it into the Epiphany Center for the Arts—a new art and event space complete with etched glass windows made by Kimberly’s company all those years ago. 

Searah Deysach and Dawne

In September of 1998, Searah Deysach was a young grad student at SAIC. She lived in Edgewater with her ex and her brother, which provided some fuel for her desire to expand her social circle and find a date. Luckily, her coworkers were prone to examining the Reader Matches and Missed Connections at the office, though few of the ads in the sparse Women Seeking Women category ever stood out to her. Until this one:

Kick-Boxing Babe, SQF, 5’ 4”, 28, tattooed grad-student is sparklingly smart, glitteringly sarcastic, simply fabulous, funny, queer, has good politics, is a touch hard-boiled yet a giver of tender back rubs, an occasional Xenaphile, full time vegetarian. ISO NS lefty queer cutie-pie with a strong personality, 25-30s for articulate romance.

“I liked all the things she mentioned and it felt different than the others I had read,” Searah remembers. “There was nothing about how she looked or how I should look, and I thought for once maybe I would fit the bill. But I was terrified to actually answer it.”

She continues, “Finally, on the last day that her mailbox was open, my best friend/ex/roommate locked me in my room until I had left her a message. I told her that I swore like a sailor and drank a lot and was fat and grew tomatoes in my garden. She called back and I nearly DIED, but we had a long conversation followed by a first date at [vegan restaurant] Amitabul. She drove me home and I gave her some tomatoes from my garden, and she gave me the sweetest little kiss that caused me to drop my keys under her car as I was getting out.”

The original ad—which ended up winning Reader Matches Ad of the Week—was placed by Dawne, a Logan Square resident. After the first date and tomato handoff and perfect kiss, Searah and Dawne continued seeing each other and have now been together for 23 years. They have a kid together and live in Rogers Park.

Patricia Simon and Colleen Fallon

A couple decades ago, placing newspaper ads was one of the main way for lesbians to meet each other outside the gay bar scene. Evanston’s Patricia Simon placed an ad in the Reader in November 1992, hoping to make a connection. Colleen Fallon answered the ad, and after a few phone calls, the pair met up at The Closet, a lesbian bar on N. Broadway.

Patricia remembers Colleen buying her a beer; a performance by Patty Elvis, a female impersonator; a birthday celebration for another bar attendee, including cake; and an overall memorable night ending with the bar’s closing at 2 AM. Despite Colleen’s refusal, Patricia insisted on driving her date home, only to realize she lived about half a block away from The Closet.

Patricia’s Matches ad

Then, Patricia describes, “We shook hands and said goodnight. Yep, we shook hands.”

The couple dated for two years, and then got married on July 5, 1994, but only after swearing to the pastor that they wouldn’t post pictures or communicate in any way about her officiating a queer wedding, for fear that she would be removed from the Presbyterian Church. Twenty years later, on July 5, 2014, the couple got married legally and openly by the same pastor.

They now live together in North Barrington, Illinois.

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