In February 2009, the Globe Magazine debuted Dinner with Cupid, a column that aims to match up Boston’s singles, send them out on blind dates at local eateries, and have them report back about what happened. It was one part social experiment, one part schadenfreude for the smug married crowd, and one part journalistic attempt to document that fundamental aspect of the human condition — the quest for love — often left unexamined in the news section.
Ten years, thousands of applicants, and nearly 500 dates later, we’re here to report that, despite superhuman attempts, no happy nuptials have ensued. (At least, we’re still waiting for that wedding invitation.) Like our singles, Cupid has suffered through the indignities of the dating life. We’ve been stood up, ghosted by daters who dined on our dime and were never heard from again, and snookered by those who showed up looking nothing like their profile pictures. Together, Bostonians have borne witness to this human parade of mismatches, swapped insults, and, perhaps most crushing, couples who had a pleasant encounter but reported “no spark.”
But we’ll keep on keeping on. To fete the column’s anniversary, we assembled some of our liveliest former daters on a frigid winter’s night at Assaggio restaurant in the North End for some behind-the-scenes dishing. We asked them to fess up about what really happened during and after their date, how they feel about the Cupid experience, and their ongoing search for modern love. And, we schemed, might romance strike the second time around?
After introductions and a glass of Prosecco, our fearless daters spilled some surprising revelations. What they reported back to us, for instance, may not always have been entirely the truth. One admitted that she wasn’t physically attracted to her match right off the bat but didn’t want to state that harsh reality in the column. Another confessed what readers have often suspected: Her excuse about a subsequent engagement — in this case, a friend’s birthday party — was invented to make for a smoother getaway.
What drew them all to apply in the first place? Some were egged on by family or friends, while others simply never thought they’d be picked. “A little bit of exhibitionism,” says 30-year-old copywriter Barry Epstein. “A little bit my mother. And I wanted to try something new, because nothing else had been working.” (Epstein took heat for asking how much his date paid to rent his apartment — but he maintains the question was prompted because his date bragged about his swimming pool.)
“I wanted to meet someone totally outside my circle, because I always date the same person — and you set me up with the same person!” says Emily Kanzer, 27, who was improbably matched with a handsome man she’d met when he was her Lyft driver.
Despite the questionable results, the small group at the reunion reminisced fondly about the experience. Even after an ill-fated evening with a van-dwelling comedian, singer-songwriter Kayla Mercuri, 24, retains her faith in the blind date concept. After all, she says, “It worked for Meghan Markle and Prince Harry!”
No regrets, confirms Jayme Lee, 28, whose “awkward” encounter flamed out after he crushed his match at three games of pool. “That backfired, much like my dating life,” he quips. “I was like, I got to go, my laundry is in the oven; we do a handshake, awkward hug, and walk away. I didn’t read the article after. . . . Wait, there were comments?”
Indeed. Our singles agreed that one of the most valuable, if a bit painful, aspects of the Cupid experience was the unvarnished public critique of their dating style, whether from what their match said about them in our write-up or from the online community of opinionated commenters. “That was kind of why I went on the date — to find out if they would tell me something that other past dates hadn’t told me before,” says Ashley Slay, whose date described the 29-year-old social worker as “too logical.” She gleaned a valuable life lesson from the experience: Be more open-minded about potential dates. “Maybe he wouldn’t be someone I was physically attracted to, or had things in common with, but let me give it a shot. That’s a philosophy I would take into other dates.”
Lesley McGee, 28, also gained insight after she gave her outing an A- and expressed interest in a second date with her match; he shot her down. “I thought we were vibing!” she says with a laugh. “I interpreted it as this great date, and he was like, ‘She was so cold.’ I brought that to my therapist. I was like, ‘Look at this! I need to be warmer, so people interpret me differently.’”
Our singles agreed that the number one pitfall of modern dating is ghosting — having your love interest vanish without explanation. “There is no accountability anymore. Ghosting is rampant,” says Jayme. “I’ve been ghosted before; I’ve ghosted people before. It’s not a cool thing to do, but it happens because of this swipe culture. Now, if something doesn’t work out, I text and tell them, ‘Hey, it was great meeting you, but I just don’t think this is going to work out.’”
Emily’s aggressive response to ghosting left her fellow daters in awe. “I don’t get ghosted — I don’t allow them to,” she says. “Whenever someone ghosts me, I send them ghost emojis until they reply. Then I say thank you.” Nowadays, the challenge is not just getting a response to texts and calls, Kayla adds. “There is social media: Is he liking my pictures? Are we Snapchatting? It’s another added element. To be honest, I don’t want to add guys I date on social media because it makes it too complex.”
Dating a stranger seems to be a double-edged sword. The benefit, according to our Cupid alumni, is the lack of overlapping social circles and gossiping among friends when a first date crashes and burns. “People would rather go through an app than a mutual friend,” says Ashley. “I’ve gone on a date after talking to someone for half an hour. I don’t put a lot on my profiles. I’ll share what I feel like sharing, and you figure out the rest.”
But that anonymity makes safety a more pressing concern. Our female daters say they have friends monitor their whereabouts during dates through the Find My Phone app, or they give fake names on dating apps to ward off creepers. (Cupid daters learn only their date’s first name beforehand and don’t see a photo — and no contact information is shared unless they choose to do so.) They know how to reverse search a cellphone number or do a Google reverse image search on a profile picture. “The rule in my house [is], if someone is going on an apps date, they tell us where they are going, and if they go back to their house, they text us the address,” says Kathryn Peneyra, one of the rare daters who did go out a few more times with her match.
The risk is real: Women and men they know have had their drinks spiked with roofies. For Emily, the age-old debate of who pays on a first date is filtered through this prism. “It’s really hard to be a woman in the dating world, and [paying] shows an understanding. I’m sitting there like, is this guy going to murder me or whatever? I took a risk meeting you, so you should pay. We are afraid of men. What are you afraid of?”
The answer to that comes swiftly from one of the men.
For all of the drama, these daters have faith that the apps’ algorithms will ultimately pay off. “Everyone in the ’90s just married someone they went to high school with; it was a finite pool and you just picked the one you liked,” says Jen Deahl, whose A-rated date led nowhere though they swapped Snapchats. “Now, it’s unlimited options and you can find someone better, but it takes a bit longer. I don’t mind waiting to meet the right person that I’ll actually have something in common with . . . I think it might be worth it. Check back in a couple of years.”
Our daters say the Boston scene also has its downside, with ambition too often prioritized over romance. “Boston is a cold city for dating,” laments educator Kyle Crosby, who memorably brought a vase of flowers for his date. “You get jaded fast,” says Lydia Zepeda. “People are here for their careers.”
“I don’t go on dates at all,” says Tucker Berk, 27. “I’m trying to get into med school — I spend my days in the library.” His 2015 Cupid match went well, but she turned out to be a college friend’s ex-girlfriend, which made him feel awkward. “My regret was that I never followed up. My grandmother tells me I should text her again. She’s desperate [for me to find a girlfriend] at this point,” he says, laughing. “I hope to get back out into the world. Maybe.”
Josh Roberts, who both works and attends grad school at Northeastern, is also not actively looking for another partner after recently ending a long-term relationship. “My life has been obsessed with finding the right person and getting married,” he says. “My parents had this storybook romance; they’ve been together 53 years. As I’ve gotten older, I realized that is not really what I want. Finally, at 34, I am concentrating more on me; my focus is my career.”
But Ben Raphel, 33, who chatted about his Cupid date with Alex Trebek during his 2017 appearance on Jeopardy! , found that Boston has a better dating pool for career-minded daters in their late 20s and early 30s than Louisville, Kentucky, where he used to live. He met his current live-in girlfriend on JDate a month after his 2016 Cupid pairing.
At the anniversary event, he tried to give the other singles matchmaking guidance, suggesting some offline venues — the gym, Meetup groups, the bar scene. The group found flaws in all of these options. Too potentially awkward. Too desperate. Too noisy.
“They say the right person comes along when you least expect it,” says Lydia, who found that her Cupid date checked her parents’ boxes, not her own. “My friends and I made it our 2019 goal to go to an event every month,” says Kayla. “It’s an excuse to see each other, but also if we happen to fall in love, yay!” Those looking for love need to try harder, Tucker says. “If you’re looking to spend your life with someone, you should really put your time in.”
Perhaps that is why these singles were willing to brave the elements on a January evening and give old-fashioned romance another whirl. If the reunion failed to produce any sparks, the quest will continue. “I want people to approach me in real life,” Lesley says wistfully. “I feel like I look unique enough — just approach me. It hasn’t worked, but that’s the dream.”