The names are fake, but the stories are real. For a year now, The Grid has been publishing weekly “Dating Diaries,” which are first-person accounts of a date that went very right, very wrong or very weird. It’s such a simple concept—our diarists tell us what went down and score the date out of 10—but what emerges from the safety of anonymous self-reporting (and a few too-personal follow-up questions from me) is an idea, casually instructive and occasionally profound, of what’s really going on in the dark every day of the week in Toronto.
Who, why and especially how we date becomes an increasingly resonant question in early February, as the scent of cinnamon hearts gets stronger. No matter how settled or single you are, Valentine’s Day demands some amount of reflection on life and love. Toronto is known for being a hard place to date: street-corner come-ons and barstool pick-ups are simply not a big part of the culture. Dating Diaries shows us the horrible, hilarious, sexy, sweet and strange moments that we might be too polite to talk about otherwise.
The worst dates are, obviously, the best. Three of the most-read Diaries on our website are: “Nicole and Edmund,” about a date that devolved into a stalking situation so bad the dater called the police; “Adriana and Paul,” in which our dater was thrown (with her dog!) into a closet when Paul’s mom dropped by unexpectedly; and “Warren and Kathleen,” a particularly epic tale of “she’s just not that into you.” I’m the only one who knows who all the diarists are, and I can attest that they represent a uniquely Torontonian cross-section of communities, interests and backgrounds. (A caveat, though: It’s all too straight, because convincing gay men and women to participate has proven to be nearly impossible. I dunno why. Email me.)
Our readers tell us they love to be privy to the ever-unfolding, overlapping, messily constructed arcs of how two people get together, fall apart and get together again. From formal dinners and drinks to an evening spent crawling through a park zombie-hunting; from awkward handshakes to earth-shattering stranger-sex; from instant repulsion to actual love at first sight, these dates tell us there’s no right or wrong way to do it if it works for you.
In this special Dating Diaries package, you’ll read about four couples we set up on blind dates, dozens of singles’ must-haves and dealbreakers, the top dos and don’ts we’ve learned from the Diaries, best date recommendations, a date-outfit focus group and more. Happy hunting!
Pam, 31, hospitality manager. Looking for: Easy-going, sense of humour, athletic. Deal-breaker: Not liking my friends.
The Toronto Singles Photo Gallery
We put out an open call for single people in Toronto to be part of a special shoot with photographer Geoff Fitzgerald. Perhaps your Mr./Ms. can be found right here?
We hook you up
We sent eight seemingly decent people on four very blind dates at two very charming first-date spots: Lucien Restaurant on Wellington and Salt Wine Bar on Ossington. Then we sat back and waited for…well, anything.
The Dating Diaries Hall of Shame
Here are the 14 most important lessons we gleaned from a year of Dating Diaries.
The Best Places to Meet Other Singles
According to Toronto singles.
DATING DOS AND DON’TS
Do Be a Good Conversationalist
Tips on how to avoid those awkward first-date silences.
Don’t Order the Gorgonzola
We asked Rob Gentile, executive chef of Buca to select the most first date–friendly (and unfriendly) dishes on his menu.
Do Be Safe
Follow these basic first-date safety rules—and they are basic, people. Tell your friends.
Don’t Go to a Comedy Club on a First Date
Seriously—take it from comedian Ennis Esmer.
Do Know What You’re Getting Into
How do you determine which online-dating site is for you? Consult this streamlined guide to the most popular web-based matchmakers.
Do Have An Escape Plan
Don’t worry if your date isn’t going so well—you can always bail using one of these foolproof escape plans
Is this a good date outfit?
Our unattached fashion columnist took to the financial district with a single friend in tow to see which first-date outfits flew with passersby—and which flopped.
