Her Billionaire Toy Boy

Chapter 2

The Game was a longstanding tradition of which Sam was not quite proud, but he was not sufficiently embarrassed about it to discontinue, especially given that leaving the game would mean that his opponent—his friend Damien from school—would win.

He couldn’t let someone else win the game.

Not after this long.

The game had started when they were in school and neither Damien nor Sam particularly had much game. They weren’t particularly good at flirting, or speaking, or going to social events, or anything, which might have put them into the favorable proximity of a beautiful woman. However, they both wanted to be. They felt that they needed some sort of higher-stakes ‘gamification’ in order for the dating scene to work. Their competition against each other had provided the only workable motivations. It made sure that they got their work done for school, that their hobbies were flourishing (Damien being a burgeoning screenwriter, Sam already building the business model for what would come to be the most highly-ranked chain of vineyards across the eastern seaboard), and that they stayed on top of their nutrition and worked out regularly.

So, late one night, they started an ongoing competition: The Game.

The Game was simple: The more ladies each of the young men got to go out with them, the better. The one with the most at the end of an unspecified time segment would win. Neither of them specifically knew at what point the game would end. Often they celebrated minor victories at the end of general epochs of time—the winner at the end of college; the winner after a trip abroad; the winner after a summer in the Hamptons or even just the man with the most phone numbers at the end of a party attended in Manhattan.

To make the game more interesting, at one point either Damien or Sam (neither of them could explicitly remember which) decided to add subcategories to the game. It was well known that the best way to add more enjoyment and pizzazz to anything was to increase the amount of granularity. And so there were now sectors in which to focus: which man could get the most girls with red hair, who were still in college once they were slightly out of it, waitresses—the list went on. It wasn’t not a misogynist institution, but neither man was really thinking too much about that aspect of it. They prided themselves on being fun and generous when they did go out with these women. As much as it was a numbers game, they tried not to be too mercurial about it.

Yet it was always there, and it had been none too flattering of a revelation when past girlfriends had found out that they had only been recruited to diversify their boyfriend’s dating portfolio. After a few devastating repetitions of this entirely avoidable tragedy, Damien and Sam looked at each other and made a promise: No one would ever know about the Game. Which, of course, made it completely inevitable that the secret—once it came out—would be even more calamitous. However—again—neither man tended to think too much about it from this point of view.

However—they still texted each other whenever they seemed to be jumping ahead within the game. Sam had walked up to Mira because she was beautiful, yes, and because he needed input as to how to run his bar, yes, and also because she seemed like she would be a wonderful person to speak to and share a glass of his hopefully above-par wine; but, also because he was trailing woefully behind when it came to his perusal of women who were older than him.

Damien had crowed about this just the other day. “Well, Sam, of course, you’re leading the board with college girls,” he said. “They’re inexperienced! They’re young! You represent the older man, a man of power, a man of mystery—a man with money. All you have to do is shower them with gifts and you have their phone number. Nah, man, count me in for older women, any day. They know what they want. They know who they are. They’ve lived a little—they’ve got stories to tell. Trust me.”

Damien’s enthusiastic pursuit of women, only slightly older than himself, was based upon the indisputable fact that he was winning by a very large margin in that particular column of the spreadsheet they kept between them, detailing their exploits within the game.

Whenever Sam looked at this spreadsheet, he felt a little queasy. Was this the best way to be going about meeting women? Was this a particularly respectful way to treat other human beings—reducing them to a number within a cell, within a bantered-over set of columns? Probably not, he admitted to himself. But it was fun, so, that excused things—for a while.

Damien, at least externally, was far less conflicted about the game.

Only a few moments had passed after Sam texted him, immediately after Mira had left the bar, before Damien’s thought bubbles began to appear on Sam’s screen. Then Damien’s words appeared: Congrats, man! Talk later. Currently getting points myself.

Sam wrinkled his nose at Damien’s words. “Getting points myself.” Sam shuddered. But then, he was doing the same thing.

He looked at the ceiling and scratched his neck. He’d thought several times about getting out of the game. But Damien was one of his oldest and closest friends. If nothing else, Damien had tons of dirt on Sam which he could use as leverage—which Sam somehow knew Damien would do if Sam tried to leave, as Damien clearly loved the Game. Plus, he reasoned, it was a good thing, ultimately. Sam treated every woman he dated with generosity and respect, and it certainly got him out of the house more.

He realized that he was just thinking this way to make himself feel better. He frowned and put away his phone. Then he took it out again and looked at the seven digits which made up the phone number which tethered him, however remotely, to the fascinating woman with whom he had spent a few merry hours earlier that evening.

There was the whole business about the points. He couldn’t ignore that. He should call her on that basis alone. If he didn’t, Damien wouldn’t ever let him forget about it. But there was something more—something deeper. Sam shut his eyes and thought about the deep wryness that he’d seen in Mira’s eyes, the world-weary air she carried about her, the way she carried herself with poise and maturity, the way she’d seemed to know and yet simultaneously appreciate the punchline to the jokes he’d tried to make…it had made it feel like they had a shared past which, of course, didn’t exist…