How can singles find the partner of their dreams, especially in a society that demands instant gratification? In today’s age, many turn to dating apps, but since their user base has plummeted after 2020, and since Bumblegate exploded earlier this year, those apps may no longer be an option for some.

Without the apps, many singles seeking partners have turned to local dating events, speed dating, and even matchmaking.

Traditional matchmaking has been around since the times of the Torah. And for singles looking for the cure to singledom in the modern era, ads for these services can be found on Google and social media. Indeed, a single friend of mine showed me the barrage of Tawkify and Modern Matchmaker ads on her Instagram back in 2023. She tried Tawkify for a year — after paying the $4,000 price tag — and never landed a single match.

But does matchmaking work for some? And if it does, how does it work? When I asked these questions in a Facebook forum, I ran into Ashleigh (Pittsburgh City Paper is withholding her last name for the sake of anonymity). Ashleigh worked as a matchmaker back in 2003. And although it seems as if the dating landscape has changed dramatically since then, it very much has not.

Ashleigh’s story begins with a bucket of junk mailers and hope and ends with frustration and lawsuits.

When she first started at The Right One in Pittsburgh, Ashleigh had to travel to Omaha for training. “It was the most successful branch in the country … run by consummate professionals. There was a reason that they had success. And when I met the people in Omaha, I felt like I could build my career in this industry,” she says.

The Right One was a matchmaking franchise with offices all over the U.S. Back in those days, users were recruited through widespread mailers as well as through signage posted around the area.

Singles at the end of their ropes would find these mailers or billboards and call in, hoping to find their perfect match, according to Ashleigh. “We had people in a sales role to get folks through the door and … get them to enroll,” she tells City Paper. “The sales script said things like, ‘How did you spend last Christmas? Oh, you were alone. Would you also like to die alone?’”

Ashiegh hated the scripts but understood their psychology. “They were doing it because the packages were so expensive. In 2003, it cost $2,000 for only three introductions, and people could put down a sum of as little as $1 (with 21% interest noted in small print). People were often not reading that contract because, again, they were in this highly emotional space where they were afraid of dying alone … It was all highly, highly manipulative,” she says.

Ashleigh’s role was to comb through filing cabinets for dating profiles complete with Polaroid pictures. The profiles included their hobbies, what they were looking for, and details like religion, smoking or non-smoking, and kids or no kids, much like a modern dating app profile. But when it came down to it, most matches didn’t even get down to the fine details.

“The whole thing was sold as personalized matching, but to even get to any matches, we just had to start with three things. Number one, we had to look at the age range. And that got so complicated, because most of the men wanted to date women in their twenties,” she says. “And I was [in my twenties] at the time. So I’d have men in their fifties be like, ‘I’m just really looking for someone like you.’ And I’d have to remind them that they had daughters my age — it was on their profiles. We had hardly any customers in their twenties.”

Then, if Ashleigh could find somebody within the preferred age range, she had to look at smoking, and then distance. “Customers were allowed to say exactly how many miles they were willing to travel,” she recalls. “And this sounds so archaic, but I remember we had a program called Microsoft Streets and Trips, and we would put the addresses into it and be like, Oh no, it’s 29.1 miles. They’ll only go 25. So then I’d have to hop on the phone and ask, ‘Will you travel four extra miles?’”

By the time Ashleigh worked through those initial preferences, the matchmaking service’s file cabinet was down to hardly any people, “so we never got into compatibility, things like hobbies and shared values, once those basics were filtered through, even though we had a very large clientele.”

When clients were matched, they received a slip of paper in the mail that listed the person’s height, eye color, hair color, job title, one or two hobbies, and their phone number. “When you paid $2,000 for three matches, that [slip of paper] counted as a match. And if people didn’t contact each other, it still counted against their tally,” she says.

According to Ashleigh, female clients became upset when their male matches did not make the first move. Unfortunately, these matches still counted. “Our clientele was always so angry. I had to develop my customer service skills very quickly,” she tells CP. However, the contracts were so airtight, people never were able to get any satisfaction out of their anger. “The owner of the company was always in court, being sued left and right, and she always won.”

A WESA article from Sept. 2013 investigated Talar Enterprises, operator of The Right One dating service in Pittsburgh. In 2008, the service changed its name to Two of Us Pittsburgh, and now the company is known as Pittsburgh Singles. The article highlights two court cases with dissatisfied customers and states that there were at least nine lawsuits at that time.

Although The Right One’s Pittsburgh franchise was troubled, Ashleigh learned a lot during her time there. “I always say that I was forced to confront some really ugly truths about humanity that had not been previously known to me, so it was eye-opening in ways that were both overall good for me and painful at the same time,” she tells CP. “From a professional standpoint, it was helpful learning how to deal with angry, distressed people and de-escalate them. I’ve needed that skill in every job I’ve had.”

When asked if there were ever any satisfied customers, Ashleigh’s answer was yes, but … “My childhood pediatrician [found her husband] through the service. There were success stories, but I always felt like that was just … coincidence. It wasn’t because of artful matchmaking.”

Ashleigh is now happily married and working as a professor. I asked her what she believes the future of dating looks like. “I think people need to remove their egos and their ideas about what they deserve, because that’s where the impediment is,” she says. “Often, people look at a person’s height, salary, weight, or whatever and think they’re better than that. My husband is someone I would have overlooked ten years prior, and I would have said, well, he is not exciting enough, or he’s not this or that. I had to be humbled by life to be able to see his value: that he is genuine, funny, and kind. I have a really nice, lovely, easy marriage now, because I did knock myself down a few pegs.”

So, what is the best way to find love? We here at Pittsburgh City Paper are launching a personals column this summer. Do we believe we are the tried and true answer to finding the one? Not exactly. But what if, instead of tooting our horns as the best way to find your perfect match, we simply offer another option for finding a connection? No guarantees.