4. Ashley
FOUR
ASHLEY
I stare at my phone, contemplating the message Sebastian sent earlier.
Sebastian:
Hey Ashley, thanks for everything last night and for considering my proposal. I hope all is good between us. I’ll send the paperwork for Single In The Six to your email today.
It’s succinct, like a period at the end of our brief fling. I suppose this is better than a drawn-out talk about our emotions, but it leaves me feeling like he’d checked a box.
You’re the one who pretended to be asleep. I ignore that thought.
I leave it for an hour and a half, just so he’ll know I’m not in a rush.
Instead of replying, I force myself to focus on work, the way I’ve been distracting myself all morning.
It’s a busy season at the marketing firm where I work, and one of my regular clients is working on a rebrand.
I check some analytics for that portfolio, then respond to a message from my manager about some invoices.
When I reply to Sebastian, it’s as blasé as possible; if he’s going to act like nothing happened, so will I.
We both know this can’t go anywhere. He doesn’t do relationships, and that’s what I’m looking for, even if the work situation wasn’t already a complication.
Still, would it have killed him to act at least a little conflicted about it?
After I request the paperwork, I do some digging on dating influencers, my heart sinking at how many male podcasts focus on getting laid and how few accounts actually discuss finding healthy relationships.
Maybe I have the chance to do something useful here and open a dialogue about dating in this city.
I tell myself that’s what the butterflies in my stomach are about.
That they have nothing to do with Sebastian Rossi.
There are few things I enjoy more than an easy run with my best friend while we get caught up on life.
I meet Laurel outside my building to run five kilometers around the neighborhood.
I like living in midtown with its mix of shops, restaurants, apartment buildings, and older houses that I’ll never be able to afford.
It’s close to the subway line, but not as hectic and crowded as the downtown core.
Laurel and I are bundled up against the late January chill.
She’s wearing earmuffs over her long dark hair and an LED vest that makes her look like an extra from some sci fi movie.
The drivers will certainly see us now. I’ll bet Cal bought the vest since he’s very into safety.
“Stevie didn’t want to come?” she asks. Stevie Choi is the third member of our trio, but her young children make workday outings difficult.
I chuckle, remembering the string of nosey texts Stevie sent me. “She was so mad she had to take the kids to piano lessons. You know she’s been dying for something juicy to happen to me since you’re boring now.”
Stevie and her husband Andy have been happily married for as long as I’ve known them, but she loves living vicariously through me and Laurel.
Her advice in most situations is to go with your heart—or some other part of your anatomy—and think it through later.
Since Laurel has been coupled up for several months now, it’s on me to bring the entertainment that will compete with Stevie’s favorite Korean dramas, and sadly, I’ve been neglectful in that department.
Laurel doesn’t protest being called boring.
We take a selfie and drop it in our group chat before starting at a leisurely pace.
We run the first few blocks mostly in silence, letting go of the stress of the day and adjusting to the cold air.
About halfway through our run, I tell her about Sebastian’s proposal.
She gets indignant, which doesn’t fully surprise me since she’s never really liked him.
They’ve only met a couple of times, but he made the mistake of flirting heavily with her, and she wasn’t into it.
I suspect she thinks he broke my heart back in the day, though I’d never admit to having had romantic feelings for him; any such feelings were a long time ago and are long gone.
Now he’s just a friend who is nice to look at.
However, I don’t plan to look closely at him for a long, long time.
“So he dropped this work collaboration, then got into bed with you? This feels like a ‘me too’ scenario.”
“It’s not like that,” I protest. “I’m the one who suggested he come over, and I initiated everything else. I know you don’t like him, but this was on me.”
She gives me a skeptical glance. “He didn’t have to go along with it.”
“You know it’s hard for men to resist my charms, Laur,” I joke.
“Well, obviously you’re hot as hell and any straight man would want to get with you,” she says in such an emphatic tone that I feel a surge of appreciation for her. “Still, I’d expect him to resist, given you were drinking and he asked you to work with him.”
“I guess so. But we have a history, and it just happened.” There’s not much more to say to justify being this foolish and letting our sex drives take the wheel for either of us.
“Did you hear from him today?”
“He sent a text. We’re working through the paperwork.”
“And you’re still going to do it?”
“Sure, why not? It’s an interesting strategy, and I’d be compensated for doing what I want to do anyway—use the app to meet eligible men. Seems like a win-win.”
We stop at an intersection, and I fiddle with my gloves, unsure about her reaction. Sebastian isn’t a terrible person, but after what happened, I’d lecture me if our situations were reversed.
She frowns. “It doesn’t feel weird, him paying you to go on dates with other guys?”
“It’s the company paying me, not him personally.
I’ll be doing marketing promos and stuff.
It’s not like they’ll tell me who to go out with or how far to go.
If I hate it, I’ll quit.” I’ve done enough contracts that I know to read the fine print.
Sebastian would rue the day he tried to lock me into a contract that left me vulnerable.
“I guess. If you want to.”
Her reluctant tone grates on me. I spent last summer focused on other people’s weddings: between my sister, my cousin, and an old roommate, I paid a fortune celebrating everyone else’s romantic successes.
By the end, I was broke and bloated from all the appetizers.
Why shouldn’t I put my own love life front and center for once?
Why does everyone else get a happy ending?
“Look, Laurel, it’s a bleak landscape out there,” I snap.
“Maybe you’ve forgotten what the dating pool looks like, but it’s getting shallower by the day.
If someone’s going to pay me to meet guys in the hopes that one of them will own more than three shirts and a folding table and wants to go to an actual restaurant before propositioning me, I’m willing to try it out.
We can’t all fall head over heels with the guy we cut off in traffic. ”
I immediately regret my words because she looks surprised, her big green eyes widening. I wanted so badly to talk to Laurel, and now I’m attacking her for voicing an opinion.
“I haven’t forgotten, Ash. It wasn’t that long ago I dated that guy who asked me to cover our whole meal, including the expensive steak he insisted on, because he’d lost a big windfall at the track.”
I snort. I’d forgotten that gem.
“And I didn’t cut Cal off!” she adds emphatically. This is apparently still a sore spot. “He was driving slowly in the left lane. It’s not my fault I’m a better driver than him.”
I’m not sure of her logic, or her driving for that matter, but I let her win this one. “I’m sorry. My head is all over the place today. I shouldn’t have snapped at you.”
“You know I just want what’s best for you,” Laurel says as we round the corner to my building. “You’ve always been the more romantic one, waiting to meet your soulmate in the most unexpected way. But if you feel like this app is the right move for now, then go ahead. I’ll cheer you on.”
She’s not wrong. She’s always been more wary of love, whereas I’m someone who cries over romantic comedies and wants the improbable Hollywood love story. It was easier to believe in romance and letting things happen in their time when everyone in my life wasn’t moving ahead and leaving me behind.
“One good thing is that he wants my feedback, so maybe I can help improve the app.”
“What do you mean? Like troubleshooting features?”
“He didn’t elaborate, but I assume I’ll have some input on their latest features and stuff.
” We discussed this over dinner, but at the time, I was mulling the social media aspect and hadn’t thought about the app instead.
I look over at Laurel, and a kernel of an idea starts to generate, thinking about the experiences we’ve had on dating apps.
She and Cal were both users before they got together, and at one point he asked her for pointers since he was a newbie at online dating after his divorce.
“Ash? You there?”
Lost in thought, I didn’t even realize we were approaching my building. We stop in front of the entrance.
“I was thinking,” I reply. “Remember when Cal asked you about dating apps, and you made a joke about not sending pictures of his junk to women?”
She snickers. “How could I forget that? He never lets me live it down.”
“Poor innocent Cal,” I say, causing her to laugh harder. “Anyway, the point is, he had no idea. I think a lot of men have no idea what it’s like for us, the kind of harassment we deal with on dating sites.”
“Okay, but what does this have to do with you?”
I mull over the idea that’s percolating. “Well, now I have Sebastian’s ear, I can press him to take this more seriously and work on strategies to deal with constant unsolicited sex invites and dodgy photos. To make the experience safer.”
“That would be great,” Laurel replies with enthusiasm. “Especially since the platform’s selling point is its local focus, which means the creep who won’t take no for an answer can see what part of the city I’m in and may live only a few blocks away.”
“Exactly!” The idea of making the platform safer for women sparks something in me. “I don’t know how far Sebastian will let me take this, but I’ll think through how to pitch it to him and his business partner.”
“Great! Keep me posted.” She turns to run the few blocks home but stops and looks back at me. “You know I’m here for you any time, okay? I might have concerns about this, but if you need to vent about this social media stuff, I’m here. I promise not to nag you.”
Ugh, I was hoping we were done with her thoughts on Sebastian. I get that she’s looking out for me and worried I’m going to get burned, but I know him better than she does. I’m not going to let my heart—or my hormones—get attached. I learned my lesson the first time Sebastian and I hooked up.
“I’m good,” I reply. “But I appreciate it.”
I watch her leave, the blue LED vest blinking as she runs down the street.
Miss Midtown Instagram Profile
Image: A thirtysomething white woman in a hot pink wig, pink lipstick, and aviator sunglasses
Bio: I’m just a midtown girl who loves fitness and having fun! I’ll be documenting my dating experiences looking for love on the Single In The Six app.
Mr. Six Instagram Profile
Image: A thirtysomething white male wearing a Toronto Blue Jays cap and Groucho glasses complete with fake nose and mustache.
Bio: Single In The Six affiliate, coffee aficionado, techie, film buff, dog lover, foodie. Watch this space for my wild adventures dating around the city.
Miss Midtown private message:
Since when do you love dogs? Have you ever even had a dog?
Mr. Six:
I like the idea of dogs, okay?
You’re the guy who borrows a friend’s pet to pick up women at the dog park.
I’m not saying I’ve done it, but I’m also not saying I wouldn’t do it.
SHAMELESS.