The Morning After
Key West New Year's
The morning after New Year’s Eve, Peachtree and I were walking when a man with an accent—Southern, I thought at first—came toward us and said, “Hey, do you happen to have a cell phone? I promise I’m normal. I just lost mine and need to make a call.”
Patrice had noticed a trike locked to the sidewalk with “Chuck’s Hot Dogs” painted on the side and assumed the man walking toward it—freshly out of a parked Durango—was the entrepreneur. I hadn’t noticed the trike, the car, or the man at all until he was suddenly there.
Peachtree stopped and looked at me the way dogs do when they realize their person is about to make a questionable decision.
The man kept talking quickly, like he’d rehearsed this. He had money. He had ID. He wasn’t crazy. He just needed to call his girlfriend. I handed him my phone. Peachtree sighed.
“I see you’re walking,” he said, already matching our pace. “I don’t want to hold you up. I’ll just walk with you.”
That was how the morning changed shape.
He told us his phone had fallen out of his pocket at the Bearded Lady bar the night before. At first we assumed he’d been drunk. It became clear pretty quickly that he hadn’t been—it had just slipped out.
His girlfriend, Jenny, had tracked the phone and the location still said it was there, but no one could find it. He dialed her number and put the phone on speaker, walking beside us like this was the most natural thing in the world.
When Jenny answered, he immediately began explaining airport security.
“Okay, so listen. You go to the TSA line. You show your ID. They take your picture and give it back. You don’t need to show your boarding pass. Then you put all your stuff in the bins. You have PreCheck, so you don’t need to take off your shoes. Then you get your stuff and follow the signs to the gate.”
Jenny sounded about forty and fully capable of navigating an airport. She thanked us for letting him use the phone. He had us say hello so she could thank us personally.
After he hung up, I realized I wasn’t worried anymore.
You can fake a lot of things. You can fake confidence. You can fake paperwork. But you can’t fake the way someone explains airport security to a grown woman just because he’s afraid he won’t be there to walk her through it.
His name was Daryl. He was from Wisconsin but worked in Illinois. He showed us his driver’s license—not because we asked, but because he wanted us to feel comfortable.
He and Jenny were supposed to be in Key West for ten days. He’d booked the hotel starting January 1 instead of December 31. When he arrived, there were no rooms anywhere except one that cost $3,000 a night.
So he took an Uber to the airport and used 40,000 Amex points to rent a Durango.
He parked it near the fire department because parking was free and, apparently, they have a bathroom. They also have a phone—because that’s where he’d called Jenny after realizing his cell was gone. He slept in the back of the Durango.
Before ending the call, he told her he’d pick her up at the airport at three.
“I’ll text you when I land,” she said.
“Well,” he said gently, “that’s great, hon, but I don’t have my phone. I’ll just be there at three, okay?”
He stayed with us for two miles, commenting every ten minutes on how fast we walked.
“Shit,” he said at one point. “You guys do this every day?”
I told him we usually walked three or four miles. My lower back was not impressed by the distinction.
Once he realized we weren’t locals, he turned into a tour guide. He pointed out a fort with a public garden he and Jenny had already visited. He showed us the Waldorf Astoria, like it was proof that something on this trip had gone exactly right.
At the Southernmost Point, he explained that it wasn’t actually the southernmost point right now. They’d moved it temporarily because the ground wasn’t secure. Instead of being ninety miles to Cuba, it was more like ninety-point-two-five. He seemed pleased by the precision.
Eventually he said he was going to get a coffee and Uber back. We said goodbye and stepped into line for photos. When we started walking again, we saw Daryl heading back the other way.
It took a minute to realize he probably couldn’t Uber.
He didn’t have a phone.
Peachtree suggested he get a burner. He wasn’t interested. He wanted to go to the AT&T store after checking the bar again when it opened. The tracking still said the phone was there. Jenny had called it—five rings, then voicemail.
As we walked, it became clear that none of this was dramatic. It was logistical. One missed detail had unraveled an entire vacation.
Daryl lived in Lake County, Illinois. His father had worked for the same company as Peachtree for forty-three years, and his mother had worked there for a time as well. He told us a lot about his father’s job—more than we could keep straight—about contingency plans and who was allowed to be where if something went wrong.
He talked the way people do when they’re trying to make sense of things out loud.
He had a cat named Walter and a rabbit named Albert. Albert ruled the house. Walter was afraid of him, even though Walter had been there first. They stayed away from each other. Albert was six—near the end of a rabbit’s lifespan. Daryl said this plainly, without sentiment.
He told us he’d found a room for $200 a night, but it was a bunk bed with four other people. That’s when he chose the Durango.
Later, he mentioned his return flight was the day before his checkout date. He was paying for a night he couldn’t even stay. He had airline status and hoped they’d let him change it without a fee so he could stay the extra day.
“When Jenny and I travel together,” he said, “everything’s perfect. This time I wasn’t paying as close attention.”
Then he added, almost cheerfully, “I’m glad she wasn’t here for the Durango sleepover.”
Only later did it occur to me that while we’d been laughing our way through one version of the island the night before, Daryl had been living through another. Same place. Same night. Two bars apart.
One of us got a hangover.
One of us got a Durango sleepover.
At least I didn’t lose my phone.



I love this!! It's the little interactions that make everything worthwhile for me!
|He stayed with us for two miles, commenting every ten minutes on how fast we walked.|
I mean, come on? How dedicated can a guy be? I hope whatever they're doing now is pleasant and free of stress.
So good, I loved the recount of this encounter. I feel bad for Daryl, but he's got such a good spirit! Despite his troubles he's just worried about his love. 🥹