On Our First Date, She Tells Me All About Her Sugar Daddy

We’re halfway through our second drink when she starts to tell me a story about the time she went on one of those websites where women look for Sugar Daddies and vice-versa — and that she found one in pretty short order who wanted to take her out to a nice dinner at a place in Manhattan that I only knew of from movies.

Even if it were within reason for someone in my tax bracket to go there, I probably wouldn’t have anyway. I’m more the kind of person who, while extremely pretentious, is also tacky and low class. I prefer forcing my shitty local haunts (that’s right, I just said “shitty local haunts,” which I think proves my pretension) on people and insist they’re part of the authentic New York City experience than make a reservation at a place that is going to blow our collective banks for just a few small portions of cuisines I don’t even understand.

Which is why she and I are at a dive bar and she is likely wishing she was somewhere else, maybe even with a Sugar Daddy.

I do not know why she is sharing this story with me.

I guess we segued to it when she asked me if I had traveled anywhere interesting recently and I responded that I had not, and she shares that she made the trek to Las Vegas for a long weekend a couple weeks prior.

“Why?” I ask, taking the bait, intuiting she wants me to ask how it came to be that she had voluntarily gone to that strange city in the desert. Visiting Las Vegas is not like visiting a lot of other places. There’s usually some sort of at least vaguely debaucherous reason, and it’s not the kind of place where you just decide to go hang out for a while unless you’re a gambling addict or some sort of affluent person. Unless you’re going for a conference for like dentists or realtors or some shit. (And that was not the reason, though she was a realtor.)

She had flown to Las Vegas to meet up with this man, the newfound Sugar Daddy, for the weekend who, it turns out, had happened to be there for the week for a tech conference or some shit and had decided to extend his time there with her.

The trip was entirely on his dime, and it was to be their second date.

“Interesting,” I say. “That seems like moving aggressively quick.”

“Well, our first night together went okay, so I was kind of comfortable with it,” she says, then proceeds to tell me all about her first date with a rich man I do not know while we are on our first date.

“He was kind and respectful, not too insistent, didn’t try to take things further than a kiss goodnight before he put me in a car to take me home. So when he proposed it, this trip, a few days later, after a few texts back-and-forth, I thought a lot about it. I was pretty hesitant, but decided I was down.”

I assume before she tells me so that things did not go so well in Nevada. Or at least I’m quite frankly kind of hoping for as much, because if she’s still dating a man with a lot of money and I’m up against that, things probably aren’t looking too great for me. This man is probably posted up comfortably in a penthouse apartment somewhere in Manhattan while I’m living in a railroad apartment with an increasingly daunting rat infestation issue, something I try to forget about nightly while binge-watching garbage via a Netflix account my mom still pays for. And I live in a neighborhood where, just earlier that week, I had to hit the deck alongside several other patrons in my local liquor store when gunshots rang out.

My assumption is correct. Things did not go all that well.

She tells me that upon arrival he took her to a lavish restaurant where they ate, drank and enjoyed each other’s company, got to know each other a little bit better.

(I am still unclear on why her date with a high-rolling dude from a couple weeks ago is what she wants to dominate our first date conversation with, but hey — what am I going to do? I just kind of sit back and listen.)

Eventually they go back to the hotel room. She tells me that things begin to heat up.

(If I was at all capable of or comfortable with confrontation this would be the moment when I would request that we change the subject to something else or suggest that we go our separate ways. I mean, everyone has a romantic past but this dialogue on a first date seems somehow beyond the pale.)

But she will not have sex with him.

“I have a three-date rule,” she explains.

“Did he know about that?”

“Not until I told him. We were on the couch making out and I mentioned that my pants had to stay on.”

“I meant did you tell him before he flew you across the country for a second date?”

“Oh. No. I didn’t.”

“Gotcha.”

“He wasn’t very happy about it.”

“I think he may have had certain expectations — ones that he hadn’t, you know, laid out ahead of time.”

“I think you’re right.”

“He thought you were gonna fuck him, right?”

Not that that’s the right thing to think, that just because you’re throwing money around and stuff a woman should want to have sex with you. I want to be clear about my stance here. All I’m saying is it’s not out of the realm of possibility to figure out that this man was pretty confident, in these circumstances, that he was gonna get laid.

“Yep. Things cooled down pretty quickly after that and we both went to bed.”

When she woke up in the morning he was gone. He’d left a note saying he had an urgent business matter to attend to, but told her to enjoy the room for the weekend and that maybe they could catch up again once they were both back in Manhattan.

She never heard from him again. Or at least not up to the point of us meeting, which has only been a couple weeks. If he did have a serious business matter to attend to, then he might still be tied up. Who’s to tell? I could still be cast aside in favor of this guy if he ends up reaching out. I wouldn’t even be surprised.

She pauses for a moment.

“You don’t think I was in the wrong, not having sex with him, do you? I felt kind of, I guess, used.”

“No, of course not!” I respond, thinking in the back of my head how bizarre it is that someone is on what is supposed to be a date with me and asking my opinion on whether she should have fucked another dude, a Sugar Daddy nonetheless, on their second date, mere moments after we have first met. “If you’re not feeling it, you’re not feeling it. I don’t know much about these arrangements but know they’re not, like, prostitution. I’m glad he wasn’t, like forceful or anything like that. But hey — at the end of it all at least you got a free weekend in Vegas out of the whole thing.”

“Thank you. Though Vegas isn’t a lot of fun on your own. And for the record, I am not a prostitute.”

“You’re…welcome? And that’s — that’s definitely good to know. It’s been a while for me but I’m not in a position where I’m willing to pay for it. Not just yet, anyway.”

“You’re a writer, right?” she asks then.

Finally, a shift to something I could talk about for hours: myself and my so-called career.

“Kind of.”

“I Googled you.”

“I’m trying to be one.”

“I wrote an essay about the whole thing,” she says. “Would you be open to taking a look at it, maybe giving me some notes?”

I tell her my hourly rate and she is unenthused — thought I’d do it for free.

I tell her I’m joking and to send it to me anyway.

I give her some notes.

We never see each other again.

I feel kind of, I guess, used. 

This story was originally published on PS I Love You. Relationships Now.