Sex & Relationships

Dating in the Digital Age: How to Find a Guy in 10 Days

Reluctant dater Chandler Levack explores the rapidly expanding, digitally daunting world of modern dating



Photograph by Jenna Marie Wakani

Five months ago, my boyfriend of two years broke up with me. My heart felt like it had been hit by a truck. We had literally spent New Year’s on a tandem bicycle. My friends suggested that this could be the summer of Chandler. But I did not feel fun or flirty—I was sad and I wanted to eat all of the cheese. While I was enjoying the comfort of mutual spooning, dating had entered a new high-volume, high-speed era in which 20-somethings like me could land five dates a week just by swiping right on their phones. The last time I was single, Tinder didn’t exist. Neither did Lulu, a forum in which women review the dateability of male Facebook friends using hashtags like #WantsKidsYesterday, nor the dozens of other new digital dating tools. Newly single at 27, I needed professional help. And so, in the spirit of total immersion (and ripping off the Band-Aid), I dove off my couch and into the world of modern dating for 10 comfort-zone-destroying days. Here, my diary.

I meet Sofi Papamarko for a coffee. She’s a pal who runs a professional matchmaking company in Toronto called Friend of a Friend. Sofi compares finding a boyfriend to sending out resumés. “It’s like looking for a job,” she says. “You have to hustle. Your friends have to know that you’re single and looking. Be online, even though it sucks. Just remember that you only need one job, and you only need one man. But there’s gonna be millions of almost-hads leading up to it.” In other words, I’m going to have to go on a lot of interviews.

I set up an OkCupid profile under the name “vampiresunday.” (It’s a play on the band Vampire Weekend, which I hope will appeal to indie rockers who own yachts.) I fill out endless questionnaires, telling the algorithm I’m a neurotic writer with thick thighs, ADD and a degree in cinema studies. According to OkCupid, I am “More Independent,” “Less Love-Driven” and “Less Conventionally Moral” than the average user. I fear for my matches. A 31-year-old greets me with a hearty “ahoy!” Many others ask for my favourite taco restaurants and acclaimed cable TV shows. I exchange messages with an arborist who calls himself “eating_almonds.” On his profile he admits to shoplifting Bioré pore strips, which I find oddly attractive. Our inbox repartee is strong at first, but soon fizzles. I vow to widen my search beyond my usual type—quirky, artsy, mad-impoverished—which has only brought me dissatisfaction in the past.

I book an appointment with Toronto dating guru Christine Hart, who runs a service called Living & Loving Authentically. She assigns me homework—write a list of 30 qualities I want in a man. We go over them together: a good sense of humour, champion listening skills, a love of books. The last time I wrote a wish list was in high school. I’m pleased that after a decade of relationship experience, I’m looking for more than just a fan of The Strokes. We determine my must-haves: kindness, compassion and someone who genuinely likes himself. I also want a guy who truly gets my kind of crazy and accepts me for who I am.


Photograph by Jenna Marie Wakani

Over chicken wings at a pub, Christina Walkinshaw, whose excellent Tumblr “My Week on Tinder” chronicles her experiences with over 50 Tinder dates, assures me the app is the best thing ever for single women. “Some girls feel like there’s no one out there, so if they meet a guy they’ll just latch on,” she says. “With Tinder, you could latch on, but you’re probably curious about the 10 other guys who are on your phone.” Christina shows me all the prospects in her inbox: 704 notifications. Her slim fingers initiate three flirty conversations with three potential dates. It’s like watching Chopin play piano. But after meeting 50 guys in person, she’s only ever been on one third date. “There’s no perfect strategy for finding a good boyfriend,” she says. “That’s why you have to try everything.” After a few hours of my own swiping, a man offers to take me to a Jewish deli and “have sex through a sheet”; another tells me I look like Rashida Jones (!). Finally, I message a cute software manager, and we meet for a drink. He looks better than in his pictures. We talk, maybe too much, about our exes. At the end of the evening, he walks me to my bike, and we share a hug. I suggest that we walk his dog sometime. The next day, he texts me dispatches from his cousin’s bat mitzvah: “12-year-olds twerking against the wall here.” We continue texting, but he doesn’t ask me out again. I’ve been put in the digital friend zone.

I go to a movie premiere party, and the director hits on me. I get his number and call, but he seems confused and asks if something is the matter. Nonetheless, we chat for an hour, but I never hear from him again. “Oh no,” Sofi scolds me later. “You never call, you text! Or you flirt on Twitter.” I file this advice away in my “WTF” Rolodex.

I meet Shannon Tebb, who runs her own dating consultation firm, Shanny in the City. Boasting a BA in sociology and anthropology, she claims to be an expert on what men want, which is, apparently, women who sport bright colours, wear their hair down and exude a “cool, funny attitude.” She tells me the best way to flirt is to comment on the situation at hand, which is why it’s easy to pick up at a dog park. I head to one near my house. I don’t have a dog, so I arrive solo, in a bright summer dress and with my hair blown out. I’m worried I come across like the creepy dog voyeur I am. “So where’s your dog?” asks a handsome guy, as I reach down to shake paws with his black lab, Rupert. My anxiety gets the better of me and I leave.

I read Single, Shy, and Looking for Love, a forthcoming book by psychologist Shannon Kolakowski. She recommends that anxious daters initiate contact frequently. After all, she says, the risk is very low: “If the person doesn’t respond positively, you don’t have a lot invested in the relationship, so it shouldn’t be as painful,” she writes. “In fact, with meeting a new person, a more realistic expectation is that it very well may not work out.” I go for a stroll in a buzzy neighbourhood, where I smile and say hello to slick yuppies exiting fancy restaurants and bearded locals walking their dogs. Most people smile and say hi back. Two skateboarders and I chat about our favourite places to hang out in Toronto. I decline when they ask if I want to smoke weed in the KFC parking lot, but I feel like I’m making progress.


Photograph by Jenna Marie Wakani

I dress in my best Zooey Deschanel outfit for a speed-dating event put on by a company called FastLife that promises I have a 90-percent chance of getting at least one match. The venue is a lounge with white couches, mirrored walls and approximately 30 chandeliers. I chug a double gin and tonic as the buzzer sounds and I begin my first of 10 five-minute dates in an hour. I talk to a FedEx manager with a sister who’s a country singer in Nashville, and a schmoozy finance guy whose wildest moment was having sex in a Gap change room. A doctor goes on a bizarre rant about proper language use. Five minutes can last an awfully long time. Afterward, I check “yes” on a physics teacher and a guy who tells me he was so nervous he almost didn’t come tonight. “I was drinking at a bar across the street,” he confesses, “and I told myself that I could either drink here alone or walk across the street and meet somebody great.” I pat him lightly on the arm. It’s a Katherine Heigl romcom moment. The next day, though, I get an email from FastLife saying neither of my choices matched me back.

DAY 9: Yes, And …
I go to an improv comedy class. My comic friend tells me it’s a great way to meet guys. We stand in a circle, repeating our names in silly voices. I don’t meet anyone, but I do get talking to a 17-year-old girl named Spencer who attends an arts high school. We bond over our mutual breakups. Spencer asks me if it gets better. I admit that at 27, relationships are mostly a process of failing upward. She says I should meet her mom, who runs Evolution of a Butterfly, which offers “erotic and holy” workshops for women seeking their inner goddesses. Its website states: “You will learn techniques on how to … create more energy around your sexual chakra.” I go to Patrusha Sarakula’s cozy house for a chakra realignment—or something. She meets me wearing a designer sweatshirt and Frye boots. She has an amazingly calming presence as she tells me, “You already have a partner—you are married to yourself. You’re already in a lifelong commitment with your best lover and your best friend.” She has an exercise in mind she says will help open me up to meeting someone. It’s inspired by Indian mystic Osho (supposedly, Will Smith’s kids also follow his teachings), and it involves compulsively shaking to a song that sounds like a rave remix of shattering glass. I try it and it’s exhausting and frustrating and I hate it so very much. The meditation goes deeper as Patrusha screams, “Shake! Harder! Let it all out!” At last the song is replaced by soothing ocean noises. Patrusha swaddles me in blankets, and I fall asleep. When I wake up, she gives me tea and dried berries. The exercise brought up a lot of feelings—anxiety, joy, fear for my life. Ultimately, it taught me that if you are willing to risk looking like a complete idiot, you can be rewarded with love.

DAY 10: A Guy, IRL
I ditch the speed-dating, the apps and the self-help gurus, and just go to a bar alone. The sex columnist Dan Savage always says that’s still the best way to meet someone. I pop into a few spots but lose my courage and bail: there’s not enough room, the wrong song is playing. Finally, I sit down at a dive bar called Unlovable, and, in the kind of coincidence reserved for romcoms, the very man who played my date in the FLARE photo shoot for this piece walks in. He’s a PhD student with a fondness for pocket squares, and he looks like Joseph Gordon-Levitt. Over beers, we talk about Whit Stillman movies and Chicago architecture. It turns out he lives up the street from me. On the walk home, I think, Hey, that wasn’t painful at all. We hug and part ways, and a few days later, I get an email from him asking me out. After 10 days, I’m not ready to make dating my full-time job, but I feel more open to possibility—I know I can walk into a bar and meet someone cool without collapsing into a pile of nerves. I’ve dipped a toe into the dating pool. The water’s fine.

Dating in the Digital Age: A Tinderella Story