Over the past two decades, I’ve kept tabs on a series of baffling personal column ads in the Toronto Star. An individual, identified only as JY, placed ads requesting meetups at coffee shops, park benches, the Eaton Centre, St. George subway station and other Toronto locales. One ad proposed marriage. A few quoted popular song lyrics, another referenced a lion that doesn’t bite and some mentioned a grandson. Others discussed an Ottawa training session, snowfall and chirping birds. The recipient of the ad was encouraged to meet at rendezvous points, wearing a green dress and carrying a book. All the ads were intended for a person named Frances, also addressed as Ms. Green, S., Ms. T and Soulmate.
Had I stumbled upon evidence of an unrequited love affair, or something more nefarious, like veiled instructions for drug deals or coded spy ring messages? My imagination ran wild.
Back in 2000, when JY began placing ads, the newspaper’s personal column was lengthy. In the ensuing years, personal ads largely migrated to various social media platforms, but JY never cut ties with the Toronto Star. When all was tallied, after 26 years of placing thousands of ads — occasionally multiple times a week — JY invested tens of thousands of dollars in the endeavour that seemed like a quest for love.
All this time, Frances seldom responded in print to JY’s messages. The few times Frances did respond, she apologized for missing a meetup or to wish JY a happy birthday. Not all her responses were as innocuous. In 2014, Frances placed an ad explaining she’d received a cancer diagnosis and required surgery.
I discovered JY’s missive by chance. For decades, my day has started with reading the newspaper delivered to my front door, front to back, including obituaries and classifieds. After a few years of noticing JY’s name pop up in the personal column, unsure what motivated me, I began clipping and dating the ads.
Then, around 2014, it occurred to me that perhaps more was going on than a plea for unrequited love.
In my search for evidence of a cipher, I enlarged several ads, taped them to the wall of my home office, and fixated on them like a frustrated private investigator scrutinizing crime scene photographs for clues. Surrounded by JY ads, I admittedly became a little obsessive.
When people came over to my home, I asked them to share their best guesses. Some believed the missives concerned illicit drug sales, others suggested a connection to organized crime or a spy ring. A few dismissed them as merely the pleas of a cheating partner.
Then, on Christmas Eve in 2021, my solitary pursuit ended when other curious Star readers placed their own ad hoping to discover JY’s intentions. The intriguing ad addressed to JY stated, “We want to hear your great love story,” and included an email address.
This wasn’t the first time Star readers had attempted to bring JY into the light. A 2007 ad asked, “Hey J.Y. Did Frances show up?” A few years later, a reader placed an ad taunting, “Hey J.Y. Maybe Frances just isn’t into you.”
The Christmas Eve ad placed by long-time friends Sue and Vicki committed to unravelling the mystery. Former coworkers in the mid-2000s, they remained in contact, competing against one another in online Scrabble games. Along the way, the friends realized they both routinely scanned the Star’s personal column for a lark and, unbeknownst to one another, had been following JY’s baffling dispatches for ages.
Twelve days after their ad appeared, JY responded with an ad of his own. He described his motivation as “private and sad,” the knowledge of which would “make you cry all day long.”
Meanwhile, eight or so JY curious Star readers, including myself, also emailed Sue and Vickie.
Since then, about half a dozen strangers, mystified by JY’s antics, have continued to communicate via email, with some threads running pages long. We’ve never met in person. An initially enthusiastic respondent keen to exchange ideas suddenly reversed course and withdrew from the group, claiming, upon reflection, that the topic was too creepy.
During the height of the pandemic, individuals experiencing lockdown were desperate for even a small diversion, and our small group of investigators considered our interest a fun and harmless way to pass the time. Eventually, friendships blossomed remotely as group members discussed old movies, shared likes and interests, and exchanged birthday greetings.
The group decided to pool money to create an additional ad. There was a lot of back-and-forth to nail down the correct wording. I recommended a bad cop approach, suggesting the ad read, “JY, the jig is up. What’s the story?” In the end, the group chose the soft-touch with an ad reading, “I can handle sad. Keep secrets, too.”
JY soon responded with a head-scratching email to the address Sue and Vickie included in their original ad, asking, “Is: Frances = Ms. Green = Sharon?” and ended with “Thank you for solving the above equation.”
By this point, we had gone down many blind alleys attempting to figure out JY’s motives. An element of paranoia crept in when a member suggested the possibility that JY was among us, possibly me, on account of my extensive knowledge that came from following him for so long.
Another theory was floated that a Star classified employee dreamed up JY years ago to fill column space, or that JY and Frances were the same individual.
In recent years, the frequency of ads slowed to a trickle. JY’s appearances in the personal column decreased to the point that in June 2024, a plea appeared for Frances to meet on their usual park bench, imploring, “One last chance from you is needed.” In the ensuing months, JY’s absence left the group’s email thread quiet. That changed on February 14 of this year, twenty months after the previous message, when JY wished Frances a happy Valentine’s Day before going silent again.
Years have passed since Frances responded to JY.
After all this time, the group never settled on a single theory about JY’s intentions, and with the trail now gone cold, I miss the email exchanges with like-minded amateur sleuths desperate to crack the case. It has been rewarding to collaborate with a friendly group of strangers striving to solve this vexing personal column conundrum. Whoever’s behind the JY persona knows how to reach us, ideally without a riddle. Meanwhile, I’ll continue to read the personal column, ready to alert the group if JY resurfaces.
