Olivia
Some people might say that walking into a wine bar in the heart of Boston in polka-dot pajama shorts and flip-flops is socially unacceptable. And those people are probably right.
They’re your lifeline and your better judgement.
They aren’t wearing the rose-colored glasses that tell you John from marketing is a good guy just because he’s a vegan. For all you know, John is running a puppy mill.
So when Sadie, who has most likely been crying at the bar for thirty minutes or more, rushes over to me, I pull her into my arms to comfort her.
I think the direness of the situation is clear.
“I hate him,” she blubbers.
And with that, everyone who was staring looks away and goes back to their own conversations. Because if there is anything people understand, it’s a date gone miserably wrong.
“I know, I know,” I tell her as I guide her back to the bar.
Her glass is empty, and her breath tells me why. That’s alright though. She’s probably staying the night with me anyway.
Sadie is a very put-together woman, always dressed to the nines, hair done in the morning, makeup routine that takes longer than it takes me to do my taxes.
Wailing at a wine bar with mascara streaks on her cheeks is not a Sadie-approved thing to allow, which tells me this wasn’t just a date gone wrong; it was a disaster.
“Chardonnay, please,” I tell the bartender.
“Two glasses?” he asks.
“The bottle,” I say, and he nods.
Then I turn back to my friend who is blowing her nose in a small square napkin meant to be a coaster.
Yes. This is an emergency.
“I hate him,” she says again, setting a snotty, wadded-up napkin on the bar top.
I snag it and shove it in my purse because it’s starting to give other people at the bar the ick.
“I thought you loved him,” I say softly. Is it the right thing to say? Probably not. But I have to start somewhere.
“I thought I loved him too, but he used me and now I hate him,” she mutters, reaching for her glass as soon as the bartender fills it.
“I’m just going to let you be in charge of this,” he says, setting the bottle in front of me.
“Okay, so you don’t love him after all,” I say.
“Nope. I could never love him. Not after what he did to me,” she says coldly as she takes a sip. Make that chug. I look back at the bartender and mouth the word water and he nods.
“Alright, sweetie. I know you told me about this guy before. But I’m going to need a little more context,” I softly explain. “What is his name?”
“Luca,” she says the word as if it tastes like a Warhead candy.
“And you work with Luca, right?” I ask.
Sadie snorts out her response. “He’s my boss,” she says, and the conversation takes a hard left turn.
Because it’s one thing to get involved with a co-worker. But going out with your boss? That’s a whole other kind of problem.
Unmatched Dating 101- Rule #10: Keep the professional, professional and the personal, personal.
In other words, don’t date people you work with.
And more than that? Never date people you work for.
Not if you value your job or your reputation.
Not that I would personally mind if Sadie got a new job.
Spoiler alert–she works at Realr.
Yes, you heard that right. My best friend works for the enemy. She’s also an avid dating app participant, which honestly gives me an advantage.
Between her working there and being very active in the industry, I have a front-row seat to the shit show, which supplies me with endless hours of podcast content. Not of her experiences specifically (that would break girl code), just generally speaking.
Because most dates that start with a digital connection end just like this.
A girl sitting at a wine bar with an entire tube of CoverGirl Lash Blast dried up on her cheeks.
“Your boss…” I echo as calmly as I can. “Okay. That makes it…interesting. So, because I don’t know this Luca–”
“Don’t say his name,” she cries as fresh tears fill her eyes.
“I don’t know your boss; just tell me where he is now? Because no offense, Sadie, but you’re making the man seem like a certified psycho and I want to make sure he’s not sitting outside in a blacked-out car waiting for us to leave so he can follow us home and shove us in his trunk.”
“Oh, he’s long gone,” she says.
“Okay…” I nod. “That’s good, right?”
“No, it’s not good!” she blurts out.
Also, just for context, Sadie isn’t always this unhinged. That’s how I know something truly unspeakable happened on her date with the CEO of Realr. That and we really need to switch fully to water, I think.
“Because he left without taking me with him.”
“I don’t follow…” I tell her.
“We have been flirting for weeks. Weeks, Livv! Ever since I was promoted to a job in design for Realr. I’ve been sitting in on meetings and going to company lunches. He even called me into his office several times to talk privately,” she says with a look.
“Privately about…?” I ask.
“Work things. But he was also very…personable with me. And I took that as a sign that he felt the same way I do,” she says. “But clearly, I was wrong.”
“I mean, you weren’t entirely wrong,” I tell her gently, clasping my hand over hers. “He asked you out, didn’t he?”
“Technically, I asked him out…” she says.
“Oh,” I say, keeping a smile.
Sigh. Alright.
Unmatched Dating 101- Rule #24: If a man is interested, he’ll ask you out.
Now I know this is 2026. I know women are allowed to make the first move. Heck, I’m all for it. But when it comes to the first date, if a man is interested, he will make an effort. Plain and simple.
Unless he’s a socially anxious, low-self-esteem guy who shakes in his boots when a girl so much as walks past him.
But come on.
We’re talking about a billionaire CEO of a dating app company, for fuck’s sake.
If I had to guess, this man is not lacking in the ego department.
“Okay,” I say. “Just tell me exactly what happened.”
Sadie takes a breath and lets it out slowly. “So we went to Antonio’s.”
“The Italian Bistro down the road. Good choice. Go on.”
“And it went great. The food was good, the date was fun. I mean, as fun as it could be, considering he is kind of a grump.”
Grumpy, oh God.
Piece of advice. A little freebie. Forget the romance tropes. They’re fun to read, but they never work out for the benefit of the FMC in real life. Not enemies to lovers, not friends to lovers, never just one bed, and definitely not grumpy to sunshine. Say it with me–opposites do not attract.
“So the waiter asked if we wanted another round,” she goes on. “And he said, no.”
“Okay…”
“I assumed he was just ready to get out of there, you know what I mean?” she asks. “Turns out he was just ready to get out of there period. He walked me to my car, and I told him to call me, and he left. No kiss, no nothing. So I came here.”
“Okay. Well, that’s not the worst-case scenario,” I say. “Maybe he just wasn’t sure how far to let things go. You know, since you work for him.”
“That’s not the end of the story,” she says, and I stop. “He did call me.”
“Already?” I ask. This is a plot twist I was not expecting. “To ask you out again?”
“No. To fire me.”
“What?” I nearly choke.
“He fired me,” she says, and my jaw hits the bar top.
“For what reason?” I demand.
People are staring again, but now it’s at me. But I don’t really care. This is crazy.
“He said I had the wrong idea about our professional relationship, and it was making things messy and inappropriate. And he fired me.”
“He can’t do that,” I say. “Can he?”
“He did,” she says, reaching for her wineglass again.
Meanwhile, I grab the bottle and refill mine nearly to the brim. Fuck it, we’ll take an Uber.
“I can’t believe it,” she sighs shakily, but I just spit out a laugh.
“I can. He’s the CEO of a dating app. If I had to guess, he’s a total fuckboy. Thinks he runs the romance world and meanwhile, he’s the king of ghosts. No. The king of catfish.”
This is my cue to intervene. I am reeling.
No pun intended. Because this is what my podcast is all about.
People putting themselves out there only to get hurt.
Only to not understand what they did wrong.
It’s one thing to lead a person on and then ghost them.
It’s another to lead them on and fire them.
This is a step too far. And considering Sadie has been my friend since high school, it just got personal.
“You know what?” she asks. “Fuck it. Fuck him. I’m over him. I hated that job anyway.”
“You loved that job,” I say, and she shrugs.
“But yes. Fuck him. And you know what? You dodged a bullet. Not entirely, I mean it’s a flesh wound for sure.
But he showed you his true colors almost immediately.
That’s better than finding how he’s an asshole weeks or even months down the line.
Leave the hurt feelings in the dust and move onto anger.
Anger drives you towards healing, as long as you don’t dwell in it for too long, of course. ”
Sadie sighs again. “I am so done with dating apps. And men. And men on dating apps. I can finally see why you hate them so much. It’s such a scam. That all men like him are. Scammers. They deserve to be alone the rest of their lives.”
“They deserve revenge,” I mutter as I take a sip of my wine.
Then I stop, frozen with my glass pressed to my lips.
Slowly, my mouth creeps into a smirk, and at the same time, an idea creeps into my head.
“Catfish…” I say.
“What?” Sadie asks.
“He’s a catfish. Acting like he’s one thing and then it turns out he’s something else entirely.”
“Yeah, I think we already established that,” she says, nursing her water.
“You know what happens to catfish in the Unmatched dating world?” I ask her and Sadie just blinks. “They get caught.”
“Okay, now I’m the one not following. What are you proposing?”
“You want to get even, don’t you?” I ask.
“I mean…I’d love to see him get beat at his own game,” she admits.
“Exactly! And what better way to do that than catfish him?” I ask.
“I know I sound crazy. And I know this sounds like something I would never do. But this man isn’t just a Realr date that wined, dined and dumped you.
He was your boss. He made the personal professional.
Which loops back to making it personal.”
“Okay… I’ve had a lot of wine,” Sadie says. “You’re going to have to dumb this down a bit.”
“He’s the CEO of Realr!” I blurt out. “Which means not only does he pull shit like this. He runs the industry that supports other people doing shit like this! Because of him, it’s never going to stop. Unless he is stopped.”
“So, what do you think we should do?” Her frown slowly turns into a smile.
“We catfish him. We set him up on a date. And just when he’s about to pull his usual stunts, we turn the gun. Beat him at his own game. Embarrass him. Defame him. The only obstacle is going to be finding a woman who will agree to do it,” I say, taking another sip.
“What about you?” Sadie asks, and I just stare at her.
“Me?” I laugh.
“Yeah! Think about it. You know the situation. You know all about the dating world. And no one would ever suspect,” she says.
And while I don’t love the idea…it’s not a bad idea.
“How would we execute it, though?” I ask. “It’s not like I’m just going to run into him somewhere.”
But Sadie holds up her phone and wiggles it, the Realr app on the screen.
“No,” I say. Then I narrow my eyes and grab the phone. It’s showcasing Luca’s profile. “Wait…is that him?” I ask.
“Yep. Hot, right?”
That is not even the word for him.
The man…is not hot.
Hot is what you call the captain of a rugby team. Hot is the lead singer and guitar player of your favorite band. Hot is the tattooed, dreamy-eyed ER nurse who makes scrubs look like the next best thing in male stripper attire.
This man is not hot…he’s gorgeous.
Olive skin. A smirk that hints at the possibility of dimples if he ever allowed himself to fully smile.
A dark brow that implies he rarely does fully smile.
A sharp nose. Sharper jawline. And perfectly groomed yet still completely tousle-able hair that is the chef’s kiss combination of dark salt and pepper.
“He’s alright,” I say while resisting the urge to fan myself. I take a sip of water instead to bring my internal temperature down. “Are you sure my making a Realr profile is the only way to go?”
“It’s the most efficient,” she says. “If you want to beat him at the game, Livv, you’re going to have to actually play the game.”
I sigh, biting my lip in hesitation. But unfortunately, she’s not wrong. So I stop biting my lips, and I bite the bullet.
“Alright, let’s do it. I never thought I’d say this, but…let’s make a dating app profile.”