“Oh gee, thanks, Bash. I’m flattered,” I reply, my tone dripping with sarcasm.
He puts an arm around my shoulders and uses his other hand to clink his glass with mine. “Ash, you’re not going on the list because then I’d have to start avoiding you, and I like you too much for that.”
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.