Two people at a hotel bar in San Francisco.
The woman is in jeans and a white duster jacket. The man arrived first and watched her cross the lobby toward him, which took a moment to recover from. They’ve ordered scotch. The bartender is being rude, which neither of them particularly cares about because they are already deep in a conversation that has nothing to do with why they’re here. Their legs are turned toward each other. Someone laughs but it doesn’t matter who started it. The bar is loud enough that they have to lean in slightly to hear each other.
From the outside, they look like two people who have known each other for a while.
They met forty minutes ago.
At some point the man notices, privately, that the thirty or so minutes they’re spending here is cutting into the time they’ll spend upstairs. He considers this. Then he lets the thought go.
Something in him already understands what he can’t quite articulate yet.
This isn’t cutting into anything. This is the whole point.
More than half of the first-time inquiries I receive ask for a dinner date or longer.
That number tells you something. Men know, whether they’ve done this before or not, that a date is different from an appointment. They want the thing that feels less like a transaction and more like… something else. They just don’t always trust themselves enough to book it.
So oftentimes they default to an hour, sometimes ninety minutes. And it’s always dressed up as a “chemistry check”.
I understand the logic. You’re nervous. You want to minimize risk, especially financial, until you know what you’re walking into. You tell yourself you’ll go longer next time, once you know it’s worth it.
But here’s what that logic costs you.
The man at that San Francisco bar, I’ll call him Chris, because he said I could, had been trying to meet me for months. The timing never lined up. When he reached back out in February, he was determined to make it work. He sponsored the trip to guarantee I’d be there when his schedule opened. And his initial 90 minute request back in September evolved into three hours.
He wrote* afterward that he’d had to mentally pinch himself at the bar because I was focusing my attention entirely on him. That the rude bartender had been a perfect ice breaker, had we needed one. That the conversation went everywhere, college football, sex work, everything in between, and that somewhere in the middle of it he caught himself thinking about how this time at the bar was eating into the time we’d spend upstairs.
And then he stopped that thought because he realized the time over our respective single malt scotches was ENHANCING the time we were about to spend together.
When it was time to leave he made himself get up and not because he wanted to. Instead it was that our agreed-upon time was almost up and he wanted, more than anything, to respect it. He suggested a restaurant because I mentioned I was hungry. Offered a ride to the airport the next morning. I declined. He called it cute.
“There will,” he texted me the next morning, “be a next time.”
A few weeks later, Chris mentioned that a man from a review board had reached out to him after reading the review he wrote (yes, I still allow reviews). Someone considering booking me, who said his review and their correspondence had made him think about adding an hour to his appointment.
I asked Chris what he thought.
He said, “Chemistry is something you can buy. Time to develop chemistry, however…?” Then, after some back and forth messages, “The extra time allows the space required to create the chemistry. And the space is the thing… which is what was hard to articulate.”
Chris is, in my personal opinion, a smart man.
Most first-time clients are nervous whether it’s their first time in general or their first time with that specific provider. While some may see this as a criticism, I think of it as just observational truth. They’ve been thinking about this for weeks, sometimes months, hell… sometimes years. They’ve built it up in their mind. They don’t know what version of themselves is going to walk through the door.
But here’s what I know: the first 20 to 30 minutes of a first meeting are almost always, quietly, about decompression over the drink, the conversation that has nothing to do with why you’re there, the freshening up. The moment when the performance stops and the actual date starts.
With an hour booking, that moment arrives and you’re already a third, or maybe even half of the way through. With three hours, it’s just the beginning.
What becomes available after that moment is not something I can manufacture on a tighter timeline. It’s not that I’m withholding it. It’s that it requires time to exist. Chris said it better than I would, “It’s not just chemistry that sets the tone. It’s the stories and conversational through-lines that continue through the rest of the meeting. After everything else, you already have a foundation to build on.”
A foundation. That stuck with me. And you can’t build one in sixty minutes. You can start one but the structure takes longer than that.
So here’s what I’d say to the man defaulting to the shorter option because it feels like the safer bet:
Book the hour or ninety minutes if that’s what the schedule and the budget allows. I will absolutely show up completely for whatever time you’ve chosen.
But, for our first date, if you can find a way to make the third hour happen, or better yet, the fourth, take it and not as a favor to me. Book it because the version of you that you actually want, the one you’ve been thinking about, the one that doesn’t feel like a transaction, that version needs room to breathe.
The man in Minneapolis who was considering adding that extra hour? He actually added it. Chris had told him to. I suspect he understood, somewhere in the middle of that second hour, exactly what the space was for.
Some things deserve to be savored and arrived at slowly.


You make a solid case for longer bookings here. I typically book 2 hours. I generally don't feel like I have the experience or skills to help co-create that chemistry, which is kind of what brings me here in the first place. I lean towards overdoing it with gifts especially before a first time meeting, but maybe I would be better served just doing a longer booking.
Couldn’t agree more. Three hours is a great first date, and four allows plenty of time for everything, although that may push the budget