Page 6 of The Billionaire Mismatch

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.”