In our first two Dating Diaries issues, we set up readers on blind dates around Toronto. That was fun—so much fun, in fact, that The Hook-Up now runs each week on The Grid’s back page, next to everyone’s favourite bit of voyeurism, our anonymous dating chronicles. There’s plenty to be learned from these stories of getting together (and falling apart), so we asked Kate Carraway, our resident Hook-Up matchmaker and Dating Diary compiler, to distill those lessons into five unassailable truths.
1. You might not know what you want
Everyone who applies to The Hook-Up fills out a questionnaire ranging from job-interview basics to the super-specifics of what they want in a date. As the matchmaker, I have two roles: hook people up based on what they tell me, and then try to find out why their date really worked or really didn’t. And having set up a lot of blind dates—using the metrics that our daters give for age, height, style, and lifestyle, plus must-haves and deal-breakers—I’ve learned that those preferences often don’t apply to how a date actually goes down. Dating is, more than anything else, chemical. What people end up liking and not liking isn’t always what they think they will, so perfect-on-paper hook-ups are as likely to come back with a score of six as they are of 10.
2. Money matters
Though the dates we send our readers on for The Hook-Up are on the house, daters cover any tips so they’ll have something to say about how the bill was handled. A good rule, generally, is that the person who asked is the person who pays. (On a date, going Dutch sucks.) However, straight first dates seem to go way better when men offer to pay. Some women will want to split it anyway, but on the short list of unforgivables, “cheapness” is a big one. It’s never about the money itself. It’s about being smooth in a potentially awkward moment, about generosity over fairness. Nothing sexier.
3. Kill with curiosity
Great first dates are a microcosm for good relationships, with mutual support and respect, and a big part of that is what you say (and don’t say). Daters expect to be asked questions and to be really listened to when they answer. When their dates only talk about themselves, or ask a question and then stop paying attention, it kills the vibe.
4. There are more straight single women than straight single men
This is true of dating in cities in general, of dating in Toronto, and of straight dates in The Hook-Up. In the aggregate, guys are less focused on commitment and can wait longer to get into serious relationships, and when they do, they have more options among women their age and younger.
5. We see you
It’s not just you on a date. It’s you, your date, whomever your date is texting or tweeting in the bathroom, the bartender’s Instagram followers, and the cab driver (and sometimes it’s me and The Grid’s readers, too). Dating has always been simultaneously public and private, but that intersection becomes even more profound as sites like OkCupid and apps like Grindr and Tinder—where you swipe left or right for “hot” or “not”—take over the dating scene. Trying to find love amid all that exposure isn’t for the faint of heart, but the brave and optimistic keep trying—here’s proof.
What it’s like out there
A super-scientific survey of 40 Toronto singles.
Click here for a close-up view of the data below.
We Hook You Up
No matter how clever the algorithm or experienced the yenta, great dates involve an alchemy that’s hard to predict. In that spirit, we recruited a handful of Torontonians, matched each one with two promising candidates, and constructed a chain of first dates. Then we waited for sparks to fly (or fizzle), hoping that one of these pairs would dare to break the chain. (Click the green links below to follow each chain.)
Dating Diaries red flags
Strange behaviour we’ve observed over the past year of Dating Diaries, ranked in order from “run away” to “file a restraining order.”
Albert becomes unreasonably competitive with Anne-Marie during a game of Settlers of Catan.
Ian pulls the “girliest wine coolers known to man out of his backpack” on a beach date with Tamara.
Lynn texts with another guy from OkCupid throughout her evening with Tim.
Chris tells Pippa, “If Rob Ford runs again, I’ll vote for him.”
Mark subjects Dariya to a 30-question get-to-know-you quiz.
Sara tells Leo, “You know, my dad really hates tattoos, but I can’t wait for you to meet him. He’ll love you!”
Aaron picks Kristine up in his “decorated magic clown van” with a “custom horn.”
Martin admits he has some “bad internalized homophobia” on his date with Bill.
This is Daniel’s first date. Ever.
The Dating Diaries Awards
Worst venue choice: Mathias takes Cherise to a cougar bar in a strip mall off the highway.
Weirdest deal-breaker: “He closed his eyes while we were kissing.”
Worst compliment: Ryan invites Christina to cuddle in a fleece blanket, then praises her “thick thighs.”
Best (?) compliment: Sam sees Liz’s breasts for the first time and yells, “These are lovely!”
Most depressing date: Laura dumps David on New Year’s Eve—and was his only ride home to Markham.
Most cheesily romantic date: Vanessa and Niles slow-dance to no music in Cloud Gardens on Valentine’s Day.
Worst view of men: Gabrielle finds them to be “broken, angry, sad, misled, misbehaving opportunists.”
Biggest 180: Alannah on Tom: “He seemed like a self-indulgent hipster brat, and I immediately didn’t like him” to “We’re still together.”
A Year of Dating Diaries: By the Numbers
4.5: Average date rating by men
6.1: Average rating by women
5.7: Average rating for straight dates
6.3: Average rating for queer dates
70: Percentage of daters who met online
53: Percentage of daters who made physical contact
1: Dates that ended in marriage
40: Dates that involved booze
“If you expect your date to end in sweaty nakedness, trade your usual drugstore condoms for Japanese brands like Beyond Seven or Kimono—they’re ultra-thin and fit snugly. And if your date leads a meat-free lifestyle, Glyde condoms are vegan-friendly.”—David Paterson, The Grid’s Sex Detective
SO YOU NEED TO GET DRUNK
“Any martini—like a gin one with a twist—is a classic way to go, and it’s all alcohol. (It would impress me if my date ordered that.) But if you’re really aiming to get drunk, a beer and a whisky on the rocks will do it.”—Megan Jones, Reposado bartender
SO YOU NEED TO SOBER UP
“Pairing alcohol with food and water will decrease the rate of it being absorbed into your stomach. But once the booze is past your belly and into your bloodstream, there’s nothing you can do except give your body time to get rid of it. Better luck (and pacing) next time.”—Denis Grant, U of T professor of pharmacology and toxicology
SO YOU NEED TO EXIT GRACEFULLY FROM A LAME DATE
“Smile, say you had a nice time, and wish the best for the other person. Don’t be rude or disrespectful. Just get through it so you can move on with no problems.”—Muhammad Saeed, Beck taxi driver