The Worst First Date Ever

My name is Brent Jacobson, I'm 52 years old, and I've been a traveling salesman for twenty-eight years. I sell industrial cleaning supplies to hotel chains, which means I spend four nights a week in motels that all smell like the same carpet deodorizer. And I'm telling you this up front because the rest of the story won't make sense unless you know one more thing about me.

I'm a virgin. At 52. Yeah.

It's not a sad story, exactly, it's just a small one. When I was 24 I had a thing going with a coworker named Donna. We dated for maybe four months and I got close, closer than I've ever been, and then her company transferred her to Atlanta and she went. I stood in her empty cubicle for about a minute and then I went back to work. After that I just never met anyone. Routes and motels and Sunday laundry, year after year. People ask why I never got married and I usually joke that nobody would put up with my driving playlist. The truth is simpler. Nobody was there.

Anyway. Last October I finally gave in and let my nephew set me up on Tinder. He's 29 and he thought it was hilarious, an old guy on the apps, but honestly it's not bad. You sit in a motel room with a beer and you look at people. Most nights it's like window shopping in a town that's closed.

Then in January, this January, right before the date this story is about, I matched with Gracie. Gracie Petrova, 47, former florist, now a line cook at some restaurant. Her pictures were her holding a huge fish she'd caught, her in a kitchen laughing at something off camera, her with a dog that was clearly not her dog. I swiped right at 11 p.m. in a motel in Davenport and by morning there was a match.

We texted for two weeks. Real texting, back and forth, her telling me about the misery of working a Saturday dinner rush, me telling her about the worst clients in three states. She was funny in a tired way, like someone who laughs because the alternative is throwing a pan. And somewhere in there I got it into my head that this was it. This was the one that was going to happen. I'm not proud of how fast my brain went there, but a guy waits 28 years, his brain gets ideas.

We set the date for a Saturday in late January. Her restaurant, she said, the one she cooked at, because she could watch the kitchen and keep an eye on things. She picked the place. I said sure.

So here's where I mess up, and I want you to follow the chain of events, because every single link in this chain is my fault.

Two days before the date she texted me: "fair warning, saturday is going to be insane, kitchen is slammed, i'll be on the line most of the night." And I read that as her being apologetic, like, sorry, I'll be busy. Fine. Then the next day she texted: "wear something you can relax in, don't dress up, it's casual." Okay, still fine. But then, the night before, she sent the one that broke me: "just order the special when you get there, i'll take care of everything else."

I sat on the edge of that motel bed in Rockford, where I'd been since Monday, and I stared at that message for a solid ten minutes. "Order the special. I'll take care of everything else." And my stupid lonely 52-year-old brain went: that's a code. That's a woman telling a man, in restaurant language, that if he shows up and plays along, she's going to take him home. Or take him in the back, I didn't get that far in the planning. I typed "what special ;)" and deleted it. I typed "got it" and sent that instead, which looking back reads like a man agreeing to a heist.

I didn't sleep much that night. I went to the pharmacy the next morning and bought things. I'm not listing the things. I ironed my good shirt anyway, even though she said casual, because part of me didn't believe her.

Saturday came, and it came down rain like the sky had a grudge. The place was called The Rusty Spoon, in a strip mall between a vape shop and a tax place, and from the parking lot it looked like a diner that had gotten ideas. Neon in the windows, but the neon spelled out something in French. Inside it was loud, every table full, plates clattering, a kitchen that sounded like a drum solo. Rain was lashing the windows so hard the whole strip mall looked underwater.

I got there twenty minutes early because I'm the kind of man who arrives twenty minutes early to everything, including his own disasters. My hands were shaking a little. I stood by the hostess stand like a lost dog until a waitress came over. She looked about 25, hair in a bun that was losing the fight, a pen behind her ear and about six things in her hands.

"You Brent?" she said.

"That's me. Brent Jacobson."

"Gracie said to watch for a guy in a nice shirt. Table for one by the window, she wants you where she can see you." She was already walking, talking over her shoulder. "Fair warning, we're two orders behind all night, Carlos is on a rampage, so if your food takes forty minutes it's not personal."

"Is Gracie, uh, is she here?"

"She's on the line. She's been on the line since four. She said she'd wave when she could." And she dropped a menu at my table and vanished.

I sat down and ordered a whiskey from a passing waiter before I even opened the menu. Double. I never drink doubles, my doctor would have words, but my hands needed something to do and my mouth needed something to taste. The whiskey came in a glass the size of a shot glass, which felt like an insult, and I sipped it anyway and looked around for her.

The kitchen pass was right there in the open, which I guess is a fancy bistro thing. And I could see her. Gracie, dark hair shoved under a bandana, working a sauté station like her arms were on springs. She was shouting something back at a big loud man in whites who was shouting at everybody. She didn't see me, or she saw me and didn't wave, and I couldn't tell which and it was making me crazier.

Then my phone buzzed on the table.

Gracie: "you there yet? order the special. Trust me. I'll take care of everything else."

I looked at it. I looked at the kitchen. She was there, twenty feet away, and she'd sent that while standing at her station. Order the special. I'll take care of everything else. While I could see her. Which meant, in my head, in the code I had invented two days earlier all by myself, that this was on. Tonight. She was telling me to order the special and she was going to take care of everything else, and everything else was me.

I put the phone face down and drank half the whiskey in one go and immediately regretted it because it went down like windshield fluid. I was sweating. In January, in a restaurant by a rainy window, in my ironed shirt, sweating like I'd jogged there. The waitress went by and I grabbed my menu like a shield.

"Hey, uh, miss? Yana?" Her name was on a tag, thank god. "What's the special tonight?"

"Salmon," she said, not slowing down. "It's always salmon on Saturdays, Carlos gets it cheap. You want it or not?"

And here's the part that should have fixed everything, the part where a normal man says yes, salmon, thank you, and enjoys his dinner. Instead I said, "She told me to order it," in this weird low voice, like we were exchanging hostages, and Yana stopped and looked at me like I'd grown a second head.

"Gracie told you to order the salmon special?" she said. "That's it? That's the whole mystery?"

"Yeah. She said she'd take care of everything else."

Yana stood there with her pen up, staring at me, and somewhere behind her a pan caught fire.

"Salmon," I said, to nobody, because Yana was already gone toward the fire. Which turned out to be a small one, a towel too close to a burner, and Carlos the chef put it out with more shouting than skill and the whole dining room applauded like it was planned.

Then Gracie came out.

I knew it was her even before I was sure it was her, if that makes sense. She'd traded the bandana for a headband thing, and she had a dish towel over her shoulder, and she looked nervous, which honestly made me feel better because I'd been nervous alone for forty minutes. She was 47, she'd told me, and she looked it in the good way, like a face that had been somewhere.

"Brent?" she said. "Oh my god, hi. Sorry. I know I said I'd wave, but then Kevin burned a towel and everything went sideways." She sat down across from me like her legs were done for the day. "You ordered yet?"

"I ordered the special. The salmon."

"Good. Trust me on the salmon, Carlos does something weird to it with butter and lemon and it's the only thing on the menu I actually eat."

"I trust you completely," I said, and I meant it in a way she was not going to understand, and she didn't, she just smiled and flagged down Yana for a water and a glass of wine.

So there we were. My first date in twenty-eight years, if you counted Donna, which my brain kept insisting on doing. The last time I'd sat across from a woman at dinner, Reagan was president. Okay, not quite, but it felt like it.

"You look nice," she said. "I like the shirt. I told you casual, but I'm not mad."

"I ironed it. This morning. Which probably tells you too much about me."

"It tells me you care, which is refreshing. Most guys show up in a hoodie looking like they lost a bet." She sipped her wine. "So. How was Rockford? You said you'd be there all week."

"It was fine. Sold a lot of degreaser. Hotel chains go through degreaser like you wouldn't believe."

"Actually I would believe it. I've worked kitchens for six years now. The stuff we use on the flat top could strip a car." She leaned forward a little. "Okay, real question. Why industrial cleaning supplies? Did little Brent dream of degreaser?"

Nobody had ever asked me a real question on a date before. Donna used to ask me questions, but they were more like tests. Gracie's felt like she actually wanted the answer, and it threw me so bad I said the true thing.

"I fell into it. I couldn't afford college, I bounced around odd jobs for a few years, then my uncle knew a guy, and twenty-eight years later here I am. Four nights a week in motels. That's the whole exciting story."

"Four nights a week in motels," she repeated. "That sounds lonely."

"It is," I said. And then, because the whiskey was doing its work, "It's very lonely."

She gave me a look I couldn't read, something soft and a little sad, and then she picked up the menu. "Okay, enough doom. You want to hear the truth about this menu? I'd be open to anything. Anything at all. Whatever you want, I'm open."

And I would like to explain what happened in my head right then, except I can't, because there's nothing dignified to explain. The code I'd invented, the one from the text, I'll take care of everything else, was still running in there. So when a woman I was already convinced wanted me said I'm open to anything, anything at all, whatever you want, my brain did not go to salmon or appetizers or the soup. My brain went straight past the menu, out the door, across the parking lot, and into the motel I had a room in eight miles up the highway.

"Oh," I said. My voice came out strange. "Anything."

"Anything. Even the trout, which I personally think is a mistake, but Carlos loves it so I defend it."

"Right. The trout." I looked at my empty whiskey glass. "And, uh. Afterwards. If I wanted. Something. Else."

"Like what, the ribeye? It's forty dollars and not worth it, I'll be honest with you."

"No, I meant, like." I could feel my ears going red. "Something off menu. Later. You said you'd take care of everything else."

She was looking at me now with a little frown, the kind you get when a customer sends something back for a reason you can't figure out. "Brent, are you okay? You're doing a bit. You're doing a bit where you talk like a fortune cookie."

"I'm not doing a bit."

"Okay, well, whatever this is, just order food and then tell me whatever it is over dinner, because Yana is giving me the look and Carlos needs hands on the line in ten." She stood up, put her hand on my shoulder, quick and warm, and said, "Ten minutes, tops," and went back through the doors.

I sat there with my ears on fire. Ten minutes. That's what she'd said. Like a countdown.

Here is what I did, and I'm not proud of it, but a man at the edge does strange things. I got up, walked past the bathrooms, stood in the