1. Sebastian
ONE
SEBASTIAN
The cold January air stings my face as I race up Yonge Street from the subway to meet Ashley, late due to transit delays.
I’m already on edge, when I hit a red light.
Tapping my foot anxiously, I check my phone in case she’s called it off.
I don’t know what she’ll say to my business proposal or whether it’s going to muddy the waters of a decade-long friendship, but I channel the illusion of confidence as I reach the restaurant door.
Ashley is waiting by the hostess, put together like she just stepped out of a magazine.
It’s been a year at least since the last time we met for drinks, but it feels like no time has passed when her blue eyes catch mine.
Her blond hair is down and windblown, and her cheeks are pink from the cold air.
I have to take a moment and remind myself we can’t go down that road again.
“Bash! It’s great to see you!” She pulls me into a hug. She smells like a concoction of tropical fruits—probably some fancy shampoo, but it makes it seem like she teleported here from the beach to this cold Toronto evening. I pull away to avoid lingering.
“I keep telling you, no one calls me Bash anymore.” I shake my head, even though I don’t mind her using my old nickname.
“Whatever,” she smirks as we make our way to a table near the back.
I found this new place serving fancy-looking overpriced cocktails, so I figure she’ll like it. I pull out her seat and she raises her eyebrows. I may not be a gentleman in any way that matters, but at least I know how to treat a date, or in this case a woman who agreed to have dinner with me.
We order our drinks and do all the catch-up things, even though with social media we’re mostly aware of major events.
I knew her older sister got married last summer, but I ask about it anyway, thinking that she’ll at least enjoy griping about maid of honor duties, but she seems uncharacteristically subdued.
“How’s Laurel?” I try to recall when I last met up with Ashley’s best friend. We’ve only crossed paths a couple of times. Mostly I remember that she’s a hot brunette, and I’m fairly certain she doesn’t like me. “Are you two still causing trouble?”
Ashley breaks into a smile that looks a little forced. I file that away. “She’s great! She’s madly in love now. They’ve been dating for a while, but still in the honeymoon phase.”
“Good for her, I guess.” She knows my thoughts about long-term relationships. “Do you like him?”
“Cal’s great for her. They’re so happy,” she says, a hint of something wistful in her voice, and I notice she didn’t really answer the question. “But what’s up with you?”
“Oh, you know me. Not dating anyone, not madly in love, none of that. My mom is doing well. She’s been single for a few years, and I think she’s happier now than with my stepdad Raymond, but I still worry about her.
” I can see Ash trying to figure out what the right response is to this, so I add, “She likes being able to do her own thing.” Raymond was nice enough, but my mom seems to enjoy being on her own now, not tied down by kids or a husband who was very particular.
“Well, as long as Liz is happy. How are Penny and Curtis?”
“They’re good. Curtis moved out recently so it’s harder to keep track of what he’s up to these days.”
I’m surprised Ashley manages to keep all my family relations straight.
Apart from two half siblings on my mom’s side, I’ve got a much younger sister from my dad’s third marriage.
That relationship didn’t last long, but Sarah and I stay in touch, usually to compare notes on the exploits of our mostly absent father on the brief occasions when he drops into our lives.
Our family updates are interrupted by the arrival of our drinks. I order a few appetizers to split.
“Cheers. Here’s to old friends.” I lift my glass, hoping to distract her from whatever seems to be dragging her down.
“Old friends,” she repeats and flashes me a smile that finally feels genuine. “It’s been way too long.”
We look each other in the eye before taking a drink, then I watch her down a third of her pomegranate mojito but resist the urge to comment.
“So, what’s this business prospect you wanted to talk about?” she asks as she puts the glass down. I guess we’re getting down to brass tacks right away then.
I clear my throat. “It’s about my dating app, Single In The Six.
” I launched the app with my friend Seth a year ago, a reference to one of Toronto’s nicknames, The Six.
The idea was to stand out in the sea of dating apps by being hyper local, allowing users to filter by neighborhood, while those based outside the Greater Toronto Area could indicate when they’re in town temporarily.
I pause, but Ashley gestures for me to go on.
“We’ve had some success in our first year, but now Seth and I want to improve our marketing game. We both agree we haven’t done enough with our social media team.”
Ashley nods. “Yeah, your content is good, but it gets a bit repetitive, and I don’t think you’re pushing the local angle enough.
” She’s in her element, drawing on her experience working in marketing for the last ten years.
I can see the wheels turning. “If you’re looking for a social media plan, that’s in my wheelhouse.
But you said your idea was non-traditional, so I’m guessing there’s something else you’re after. ”
She’s staring at me intently like she’s trying to read my mind. Maybe she can. She’s always been one of the few people who saw past all my BS.
“Seth suggested working with influencers, but we weren’t sure how that could be leveraged because we want to balance promotion with user privacy.
Then I had the idea of people who would create somewhat incognito social media accounts to share some of their experiences, which we could then share on our main accounts.
” My voice rises with excitement as I continue.
“It doesn’t need to be all sunshine and rainbows; even the odd bad date story can generate publicity.
The stories should be anonymized enough so they aren’t identifiable. ”
Ashley is so intrigued, she keeps sucking on her straw even though her drink is empty.
I catch the waiter’s eye and gesture for another round.
“So what would the expectation be for your influencers? A set number of dates per week? A payment per date? What happens if they find true love and don’t want to keep going?
” As always, her focus goes immediately to logistics.
“We’d iron that out in our contracts,” I say.
“Hopefully we can recruit people with different goals. Someone looking for true love provides a different perspective than a person looking for, er, shorter term companionship. A mix would show we’re versatile.
I’ve also offered to post on a new account, so we will have my perspective as a user as well. ”
“I like it. It’s creative, and everyone likes a good love story. Or a bad love story.” She chuckles wryly, leaving me wondering if she’s been having more of the latter recently. “So where am I in this? Did you want my input in your plan? I can take a look.”
I try to arrange my features into my best puppy dog expression, one that is appropriately pleading and slightly pathetic. “Or maybe …”
Her eyes widen. “No.”
I give her a small smile. “You’d be perfect, Ash.”
She raises an eyebrow. “Why, exactly?”
The fact that she hasn’t completely shut me down seems like a good development.
I start ticking off points with my fingers.
“First, you know about social media and marketing. Don’t pretend you aren’t an ace at that; I saw the content you produced for that fitness app, and the vegan donut chain too.
Second, you have a drama background, so you can perform and know how to separate yourself from your character.
Third, you’re funny. Whenever we talked about dating back in the day, you always managed to make the bad stories funny and the good ones not saccharine or boring.
You know how to toe the line between a good news story and a vomit-inducingly gushy one. ”
I have only vague recollections of Ashley’s actual boyfriends over the years.
There was one serious guy, but we weren’t keeping in touch then; things got a bit weird after my dad’s wedding.
However, I still remember some of her brief flames in university because she regaled our friend group with stories of dates gone horribly wrong.
“Remember Baywatch Dude?” I ask, thinking back on one particular guy who claimed to be a lifeguard—this was never verified—and who invited her back to his room, which was decorated from floor to ceiling with posters of the cast of Baywatch.
“Or that guy who wouldn’t stop bragging about winning a hotdog eating contest? ”
She laughs. “But Sebastian, he ate fourteen hot dogs. Why wouldn’t I be impressed?”
“Fourth, you’re already an app user. I think you’ll enjoy the chance to make the experience better for everyone.”
She’s looking at me like she’s not sure what to say, but we’re temporarily saved by the arrival of fried calamari, a hummus platter, and a caprese salad. She frowns in concentration like when she would assess complicated assignments back in university, so I keep my focus on my plate while we eat.
After we’ve made a dent in the calamari, she breaks the silence. “The first question is how you’re proposing to keep us anonymous. I need to keep working in marketing, and some of my clients won’t want that kind of association.”
I’ve thought this through. “You’d have a lot of flexibility with that.
You could use props like big sunglasses, or fancy hats, or whatever works for you.
” Ashley perks up like her inner theater kid is getting excited.
“You can anonymize your dates by giving them pseudonyms and removing any identifying details.”
She takes a big sip of her drink, then slams it down decisively. “Okay, I’m in.”
“What?” I expected more questions, more pushback. She’s never been someone who jumps into decisions without a list of pros and cons.
“I said I’m in.”
I laugh, though it comes out awkwardly. “I expected to work harder to convince you.”
She shrugs, and I catch a flash of sadness in her eyes, but then she smiles. “I’m thirty-two. My sister is married. My best friend has gotten all domestic. It’s time to focus on finding the right person, and it seems like a win-win if I get compensated while I’m looking.”
That sounds a little depressing to me and not like my old friend who used to make me watch ridiculous rom-coms back in our dorms, convinced she’d meet a handsome stranger in the most unexpected of places. But it’s not like I have much experience looking for true love.
“Okay then, we’re in,” I reply before she changes her mind. “I’ll email you some paperwork to get started.”
“I’ll drink to that,” she says, then realizes her second mojito is almost empty. “Should we get another round?”
I’m only a few sips into my drink. “It’s a weeknight, Ash. Are you sure?”
She smirks at me. “When did you get soft, Rossi?”
Forty-five minutes and one round later, we’re standing outside in the cold. Ashley’s cheeks are flushed, though it might be the alcohol. I should head back to the subway, but we’re both making awkward small talk instead.
I glance at the time on my phone. “Well, it’s been great, Ash—”
“Come over,” she interrupts, then her ocean-blue eyes widen as though she didn’t expect to say that. “Just for a drink. It’s not late. I live a few blocks from here, and we could have a nightcap.”
I blink. “I can’t believe I’m the voice of reason, but we’ve had a few drinks already. I’m not sure I need more alcohol.”
“C’mon, for old time’s sake,” she replies.
I should say no for a million reasons. Because it’s a weeknight.
Because I’m in my thirties and I can’t handle this many rounds and recover by morning.
Because I know where this could lead since we’ve gone there before, and now that we’re also working together, it would be an even worse decision.
Because Seth will kill me if I screw this up.
But she gazes at me with this slightly sad look in her eyes, and all the good reasons fly out of my mind.
“Of course, Ash. I’ll come over for one drink.”
We’re halfway through round two of Ashley’s homemade mojitos when I start to realize something dangerous is happening.
We started out on opposite ends of the couch, but somewhere between laughing for an absurdly long time over some reminiscences and Ashley getting up for napkins when the rum spilled, she has migrated practically onto my lap.
I put my hand on her knee, intending to move her gently off my thigh, but my brain gets locked on a memory and I’m frozen.
Ten years ago, as the dancing wound down at my dad’s wedding. I was staring sullenly into my drink, wondering why I’d bothered coming when my father had barely registered my presence, when Ashley slid a hand on my knee. “Want to get out of here?”
The rest is a haze. We went back to my hotel room intending to get wasted, but instead we lay on the bed talking, me spilling my guts about the fickleness of my father’s love. Somehow we ended up between the sheets, giving way to an attraction we’d been ignoring for four years.
“Why are you staring at the wall like that?” Ashley asks, dragging me back to the present.
I force out a laugh. “No reason. Just recalibrating.” I glance over to catch her rolling her eyes.
“You try to act like you’re so cool all the time, but you’re still a huge nerd.”
Not many people see the tech nerd in me, especially not women. It makes me feel warm inside that she still knows me like this. That despite our stupid decision ten years ago that made everything awkward, we got our friendship back on track.
Don’t fuck this up, Sebastian.
She slides even closer, laughing at herself, then runs her fingers through my hair and looks appraisingly at me. “You definitely don’t look like a school nerd.”
I lean in. “I’ve got everyone fooled then.”
“Not me,” Ashley whispers, her breath sending a shiver down my spine.
“Not you.”
I will myself to pull back, remembering the year or more of cordial, wooden conversations that followed the morning after the wedding.
I didn’t think I’d promised anything to her, but it felt like I had.
I’d let her see me at my most vulnerable, then shoved her away and slammed that door for good measure.
She said it was fine, that we were fine, but I could tell by her face that some small part of her thought things would be different afterward.
I should get up and leave.
“Bash, you’ve got something on your lips,” she says, moving her face even closer, and that’s when my resolve dies.