“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.