The really all-new dating game

After a recent speed-dating session, Lisa Zimmerman vented on Facebook. “Very awkward conversation for 2½ minutes,” she wrote. “Date ends. He turns to girls at the bar and says loudly, ‘Well, that went terribly.’ ” Zimmerman has to reveal her squeamish dating details online; those are her own rules. Tired of clubs and Match.com, the Ottawa therapist decided to outsource the management of her romantic life to her friends. She designed a game called YentaQuest, after the Yiddish word for “matchmaker.”

She unveiled the game, and its rules, at a launch party in January of last year. Participating friends find her dates, handing out cards pitching the high-spirited, petite brunette to guys in bars, at the office, even in the grocery line. (The targets must be told about the contest.) If Zimmerman scores a date, the “yenta” gets 10 points—bonus points if the date goes well. Win enough points and the player gets a prize, often a free dinner out. At the launch party, her female friends gasped at just one rule: Her threshold for sleeping with someone would be set at eight dates. “The men said, ‘I’d hold out for eight dates if I were really into her,’ ” she says.

The 38-year-old has since gone out with athletes, lawyers, artists and one secret Oxycontin addict (that didn’t go well). She has awarded $300 in prizes. “So many people over the years have said, ‘Oh, I should set you up with so-and-so,’ but they rarely do it,” she says. “It’s amazing what happens when you incentivize something.” She reviews every date on her blog. “Dating the 100 per cent artist type hasn’t worked out, so I’m looking for a dialled-down version,” ran one review. “This guy seemed in the five-to-10 per cent range, which I’m not sure is enough . . . He thought my pink feather dress was weird. I haven’t told him about the inflatable shark head.” Strangers began asking to join her private Facebook group so they could read her funny, self-depracating diary; the group’s original 25 members have grown to about 160.

Single Canadians numbered more than 14 million in 2013. Dissatisfaction with the cold algorithms of online dating has led to a bloom of creative alternatives, such as live onstage dating events, “random dating” apps and projects like this one. “A lot of good ideas come from heartbreak and despair,” Zimmerman says with a smile. Her last major relationship, with a warm and extroverted guy who adored her, spanned six years. One day, in a bedroom of the Montreal home where she grew up, he proposed. “My parents were making this big lobster dinner,” she remembers. “He said, ‘I want to marry you.’ I was like, ‘Oh, yes.’ And there was a pause, and in that pause, you think a million things.” That’s when her newly minted fiancé burst into tears. He’d been sleeping with one of their friends, he told her. Also, he’d been sleeping with prostitutes. The damage to the relationship proved irreparable.

It had been years since Zimmerman had dated. “I don’t really know how dating works,” she says. “I thought maybe other people could do this better.” YentaQuest hasn’t yet found her a match, but it’s had surprising benefits. She feels freed from the single person’s scourge: the feeling of constantly seeking—often, she says, “at the expense of whatever experience you’re in. I’m not at the concert. It’s, ‘Oh, do I talk to him, do I not talk to him? Oh, there’s the band I should be watching.’ ” Her past year has been one of her most carefree. “Now, I see a cute guy at the bar and I don’t talk to him.” The game has even brought her coupled friends into her life a little more.

There are downsides. A few friends felt her critiques of dates were too harsh (the men remain anonymous). And one evening turned disastrous when she realized her date didn’t know he was part of a game. So, lately, Zimmerman has transformed the “reviews” into a relationship blog, which doesn’t rate dates but rather uses them as a starting point for insights about relationships, love and life in general. “I was going to find a boyfriend and then I was going to win at life,” she laughs. She instead has a new avenue of self-expression. “In the fairy tales, there are only two outcomes: happily ever after or alone forever, asleep, enslaved or locked in a tower,” she wrote recently. A game can take more interesting paths.

Editor’s clarification: Yenta actually translates into “old woman” in Yiddish and is used to describe an old, gossipy woman. Shadchan would be the more accurate Yiddish word for matchmaker. Read more on the difference between the two terms here.