Why am I hiding what I do? Ever since I became rich, I’ve used my money and status to get dates. I realize I’ve never been on a date where the woman didn’t know I’m loaded.

Since Ruth has no idea, it feels almost like I can’t tell her. I’m worried it will scare her off.

And here I am telling her about how I bombed out of the whole doctor thing, as if I failed at life and know exactly where she’s coming from. The truth of it is, my business kind of took over, until I was only spending a few minutes a day skimming my study materials. After I had my first million in the bank, I forgot all about being a doctor.

I never really wanted to be a doctor, I just wanted to be rich.

Mission accomplished.

“So what do you do now then?” She asks.

“Business,” I mumble.

Not a lie, but far from the truth.

“Oh,” she says, “Like, what kind—”

The waitress arrives with our food, saving me from having to answer.

As we eat, I wonder why I’m so concerned about being less than honest. The whole reason I sought this woman out was because of a bet.

A sharp feeling hits my gut—not pain exactly, but…

Guilt. Shit, I haven’t felt that in forever. You don’t become a billionaire by feeling sorry for people. Guilt is a liability in my line of work.

So why the hell am I doing this? Winning New York’s Best Couple could easily achieved with the normal kind of woman I sleep with. Is it the bet? Is that why I’m sticking with Ruth even though it’s turning out to be way more work and risk than is wise?

It couldn’t be her, right? I’m not doing this because of her, right? There’s something oddly endearing about her, but nothing that would risk me breaking my steel resolve.

No, it’s just the bet. That’s why I can’t back down. I never back down from a challenge. I’m testing myself, making myself stronger. I probably only felt guilty because I was just thinking about my childhood. It’s not like I’m actually interested in Ruth. Right?

Ruth looks at her phone, and then up at me. “I really need to go. I’m still on the clock.”

Without thinking, I slap a few hundred dollars down onto the table and stand up.

I realize my mistake when Ruth stares wide-eyed at it. “We didn’t even get the bill…”

“You said you needed to go,” I add.

“You’re like... rich, aren’t you?” She says. “Sorry, I know that’s a rude question, but you’ve been really evasive about—”

“I don’t like to talk about money,” I say, sounding much more curt and short than I meant to.

She presses her lips together and looks down. “Sorry, I didn’t mean…”

“It’s fine,” I say, trying to sound more empathetic. “We’re two people, and if we were on an island with nothing, then money wouldn’t be a thing, right?”

“We are on an island,” she says, “Manhattan island. And money is a thing. A thing I don’t have.”

“You get my point though,” I say.

“You’re worried I’m a gold digger?” she asks. “You’re the one that asked me to lunch in the first place.”

I look at her, trying to peer through those thick glasses and really see her eyes. Seeing her stand up to me like this, I realize that I’ve only ever been with spineless women for the last five years.

Guys like Dmitri—and hell, guys like me—we see some beautiful, tall model with perfect teeth and golden blonde hair, and we think she’s confident. She’d have to be, because she can get pretty much any guy she wants, right?

Then a woman like Ruth comes along. Dmitri sees her and thinks she looks like she fell into the bargain bin at a flea market, so she must be a nervous wreck. Okay, she is a bit of a nervous wreck at times, but then there’s moments like this, where she just stands up where any other woman would kneel down.

She’s still looking at me, waiting for me to respond. If only I could really see her eyes.

“Can I take off your glasses?” I ask.

She frowns and backs away. “No.”

“Look,” I say, “I just... I want to see your eyes.”

“These are my eyes,” she says, pushing her glasses up her nose. “Unless you’ve got twelve-thousand dollars for specialized laser…”

She trails off, realizing that twelve grand is literally nothing to me.

“It’s not fair,” she says. “If I take off my glasses, then I can’t see you, but you can see me.”

“Alright,” I say, “It’s too early for that to be fair to you.”

She furrows her brows at me. “I really need to go.”

“Let’s go then,” I say, and we walk out together.

* * *

“You were the only one who showed?” Dmitri asks, laughing.

“Worked in my favor. I got some one-on-one time with her,” I retort.

“So you fucked her already?” He asks, “You’d do anything for a dare man, even her.”

I keep a poker face. Dmitri doesn’t need to know what I’ve done—or in this case, haven’t done with her—as long as I win best couple with her, I win the bet. Whatever happens along the way isn’t his problem.

“She have any weird, freaky fetishes?” he asks.

“Ear biting…” I mumble.

“Vanilla as fuck,” Dmitri says. “I still think you’re crazy. I’d put your chances of winning this bet at... ten percent or less.”

“You realize we never actually set terms,” I say. “If you think I only have a ten percent chance, then the terms should reflect that.”

Dmitri grins and stands up.

We’re waiting for a client to arrive, and he goes to pour each of us another glass of scotch. He puts the glasses down on the table, but neither of us drink. These drinks are to seal the terms of the bet.

“That’s a fair point,” he says. “You thinking money then? Like you only have to pay ten mil if you lose, but you get a hundred mil from me if you win?”

“That would be fair,” I say. “Though certainly a bit dull.”

Even a hundred million dollars wouldn’t make much of a difference to either of us. When you get a certain amount of money, it all becomes somewhat abstract.

“If you lose,” Dmitri says. “Watching you out in public with that freak and then face planting is reward enough for me.”

“You sure?” I ask.

He considers it, then says, “No, it’s not actually. Even if you lose, I assume you’ll at least have gained some publicity with her by then. So when you lose, I want you to dump her publically. Really humiliate her.”

I feel anger flare up inside me. How is it fair for her to suffer because I lose a bet? But I know Dmitri, I can’t squabble over terms this late in.

“If I win,” I say, “then I get to pick the next woman you date. And you promise not to fuck up my image.”

What I mean by that last part is that he doesn’t tell Ruth about the bet. I’m starting to think I should just date her for real, bet or no. The last thing I need is Dmitri coming in after I’ve won and telling her how this all started.

He points a finger at me and gets a big grin on his face. “Ah, you’re a tricky fucker, Eric. You’re hungry to give me a taste of my own medicine, huh?”

I nod. “And publically date, Dmitri. No hiding her away on your yacht.”

“I’d never tarnish the spirit of a bet,” he says. “Let’s drink on it.”

We clink our glasses together, then down the scotch. It tastes good, but another pang of fucking guilt hits my gut at the same time as the alcohol.

What would Ruth think if she knew about this bet? And what will happen if I fulfill the stipulation that I publicly dump her? I shake my head, trying to physically shake the thoughts away, and mostly failing.

“What’s your strategy then?” Dmitri asks. “Even if you get her to agree to some kind of world-class makeover, I don’t think you can cover up what she really is.”

I feel the guilt flare up to anger. Who is Dmitri to talk so much shit about her? She’s my... my what?

I grit my teeth and glare at him.

He cackles. “No plan then, huh?”

I realize he’s wrong though. If Ruth cleaned up a bit, that resolve she’s got, the ability to stand up to people—to stand up for herself—it will play really well with the New York’s Best Couple panel of judges. She’s working hard while studying for the LSAT, from working-class roots, just like me…

“I’ve got a strategy,” I finally say, “A winning one. You peg my chances at only ten percent success rate, but you’re underestimating me.”

“I never underestimate you, bro,” he says. “But I’m sure as hell not underestimating her.”

The anger hits me again, but I swallow it back. All I have to do is prove him wrong by winning. Convincing him now achieves nothing—it’s a waste of my breath.