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Chapter 1

Chapter 1

I wake to the silence of a city sleeping off a drunk underneath a grey-white blanket of snow. My head pounds and my mouth is dry. I step across my bedroom, through a trail of discarded clothes (just my clothes, mind you) and fill a glass with water.

My jaw aches and a first clear thought emerges through the drilling in my sinuses: what the fuck am I doing with my life?

I review the math: I’m 30, I run my own business, I work too much, I’m single. I tell myself I’m mostly okay with this. It is, like most lies, an equation.

I shuffle to the mirror, take a hard look. Eyes darkened by leftover mascara, puffy skin, face creased with sleep. But still, not bad. Not bad at all. Straight, strawberry blonde hair, Slavic cheekbones. Lithe body toned by gym sessions five days a week. It’s a look plenty of men like. And that, I think, is what matters.

I sit back in bed and check my apps: Instagram, FB, OkCupid. I sip water slowly. I count that in the last year I’ve been on 40 first dates. Most never went beyond a chat over coffee or a drink; a few led to something more. And there is one I push out of my mind the moment it enters.

I tell myself that, in my industry, 40:1 is a decent conversion rate. Of course, that’s before you break down the effort:

40 first dates. One hour each. Plus prep and travel time. And the accumulation of all those back-and-forth messages with unknown men.

I calculate that I’ve spent at least three weeks of my life talking to strangers. I close my eyes and try to call up those conversations. Just one, I think. Just one that matters.

An image from my last date drops down onto my mental screen. We’re queuing for coffee. Steam covers the windows of the café. The girl taking orders makes painful small talk.

Then I forget his name.

I panic.

Me: *thinking* What’s his name, what’s his name? Shit. Should I ask or quickly peek in the app?

Him: Two coffees, please

Waitress: Who’s it for?

Him: Tim

Me: [Thank god]

It’s true that I can talk to just about anyone for an hour, over the course of a date. But three weeks? Three weeks of small talk is a job – one I don’t get paid for. One that has produced no meaningful results in my life.

But what if, like a job, you could outsource it – or at least the parts that another person can reasonably perform? If that sounds strange, consider that I built a successful business in my 20s. And to remain successful I’ve learned to delegate.

I step out onto my balcony and look down. From the 11th floor, men and women are tiny figurines, dabs of colour in a sea of drifting white. Where are you, I think.

I reach for my cigarettes. My hand touches nothing. Three months and counting. Smoked my last one out here, in the dark, huffing it in, really trying to enjoy it. Done. Over. Pack tossed into the trash. Still, my fingers had searched before my mind caught up with them. Fumbled for that familiar shape, closed around absence.

Where are you? Not just where is he – I know where he is; if I shut my eyes I can picture what he’d be doing right about now – but where are you. The one I’ve somehow missed. Oh, it sounds terribly sentimental, terribly maudlin. It’s New Year’s Day: it is acceptable to be maudlin. I will allow myself this.

But how did this happen? Did I stay a moment or an hour or a decade too long at work and miss you in the elevator? Did we pass each other in the street? Perhaps it was something banal. I was looking one way and you the other. I blinked for a second. I looked down at my phone. You squinted and then sneezed. And if you’d looked up, instead, in that infinitesimal moment where you had your eyes shut for just a fraction of a –

How close are we now?

It doesn’t matter. But if you were a match, Tinder would tell me. It would give me your location down to a decimal point on a mile.

It’s interesting how we justify our actions. Sometimes it can be a form of lying, widening the space between ourselves and things we’d rather not face. The lie feels fresh, exciting, and the excitement drowns out whatever other voice is in our head.


I’m looking inside now, through the glass, at the contents of my life. He sat here. He stood there. He paused by the door and –

My eye latches onto the statue on my desk: a Roman bust, blank eyes, androgynous stare. She could be anything, anyone.

Is romance an intangible, or can it benefit from strategy and structure? Can I approach it like a business problem? I haven’t looked at it this way before. I don’t know why not.

After dinner, I cure my hangover with leftover wine. One glass from the bottle left on my counter, then I open another. Sitting on my couch, I surf to craigslist.

Almost unconsciously, as if the idea was lying dormant in my fingers, I’m typing up an ad. I slosh to the bathroom and back, talking out loud in my head. I will admit that I am smiling.

This isn’t about him though.

This is about me.

The Ad

“No, this is not a joke. I’m seriously looking for a person to manage my dating profiles. It is 100% legit and I will ask for up to 7hrs/week for 2 months commitment from the candidate. Working remotely.

I’ll give you full access to my online dating profiles with my real pictures and my real personal information. Your responsibility will be to search for candidates that match the profile, flirt with them online and set up dates. When you find a good fit, I’ll go on a date. If you find a match that leads to meaningful relationship that lasts longer than 2 months, you’ll get a bonus.

If it turns into a real relationship I’ll double the original bonus. 2 months commitment. Toronto-based, flexible work schedule. I will require an in-person or Skype video interview and possibly a police check at my expense (I’m sharing my personal info, no offence)

You – good communication skills, good English, good sense of humour. Suitable for a student, recent graduate or any person interested in the experiment. Preferably a woman.

Before I hit the “Post” button, I stop and listen to the faraway sound of water trickling through the pipes. Somewhere upstairs, a man (I always imagine a man) is showering. The water falls, invisibly, above my head.