Road Trip Dare

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Published 8/20/2026
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I didn't even want to go on this trip. But Leo said we had to, and Leo has a way of making things sound like they were my idea all along.

So there I was, wedged between a suitcase that smelled like his grandmother’s closet and Leo himself, who was already drumming his fingers on his knees before we hit the highway on-ramp. His dad drove. Mr. Castellano kept both hands on the wheel at ten and two, the way people did in driver’s ed videos from the 90s. He hadn’t said a word since we pulled out of the driveway.

Three hours to the coast. Three hours in the back of a sedan that still had that new car smell mixed with coffee and the faint ghost of Leo’s mom’s perfume. I already wanted to crawl out of my skin.

“I’m bored,” Leo announced.

We hadn’t even passed the first exit.

“We’ve been driving for seven minutes,” I said.

“Seven minutes is a lifetime when you’re trapped in a metal box with your own thoughts.” He stretched his legs, kicking the back of his dad’s seat. “Dad, tell us a story.”

Mr. Castellano adjusted the rearview mirror. “I’m driving.”

“You’ve been driving for seven minutes. You can multitask.”

“I cannot multitask. That’s how people die.”

Leo grinned at me. That grin. The one that always meant trouble. He had a gap between his front teeth and a way of looking at you sideways that made you feel like you were in on a joke you hadn’t heard yet.

“Dares,” he said.

“No.”

“Come on. We’re stuck here. What else are we gonna do?”

“Sleep.”

“You can sleep when you’re dead. Live now. Dare now.”

I looked out the window. Strip malls and fast food signs. A tire shop with a giant inflatable man waving his arms in the wind. The world was ugly and flat and I wanted to be anywhere but here.

“Fine,” I said. “But nothing that gets us killed.”

“Killed is boring. Maimed is interesting.”

“Leo.”

“Okay, okay. Simple dares. Truth or dare style, but only dares. No backing out.”

Mr. Castellano cleared his throat. “I’m still in this car.”

“You’re the referee,” Leo said. “You make sure nobody dies.”

“That’s a lot of responsibility for a man who just wants to get to the beach.”

I laughed. I couldn’t help it. Leo’s dad had this way of being funny without trying, like he was always mildly annoyed by everything but not enough to do anything about it.

Leo leaned forward, elbows on the front seats. “Okay. First dare. Simple one. I dare you to tell your mom you love her.”

“I do that all the time.”

“No, you don’t. You say ‘love you’ when she drops you off. That’s not the same. I want you to call her right now and say the full thing. ‘Mom, I love you.’ No context. No reason. Just say it.”

I stared at him. “That’s weird.”

“That’s the point.”

“She’ll think something’s wrong.”

“Something is wrong. You’re trapped in a car with me. That’s an emergency.”

Mr. Castellano snorted. I couldn’t tell if it was a laugh or a cough.

I pulled out my phone. Three bars. I’d lose service soon, once we hit the mountains. I called my mom.

She picked up on the second ring. “You okay?”

“Yeah. I just wanted to say I love you.”

Silence. Then: “Did Leo put you up to this?”

“Yes.”

“Tell him I said he’s a menace.”

“She says you’re a menace,” I said to Leo.

“Tell her I said thank you.”

I relayed it. My mom laughed, that surprised laugh she did when she didn’t expect to find something funny. “Be safe. Don’t let him talk you into anything stupid.”

“Too late,” I said, and hung up.

Leo clapped his hands. “One for one. Good start. My turn.”

“I dare you to sing the national anthem at the top of your lungs until your dad pulls over.”

Leo didn’t hesitate. He took a breath so deep I saw his chest expand against his t-shirt. And then he started singing. Not well. Not even close. He hit every note wrong, on purpose, his voice cracking and soaring like a cat being dragged across a chalkboard. He sang through the first verse, the second, his face red, veins popping in his neck.

Mr. Castellano didn’t pull over. He just turned up the radio.

“Cheater,” Leo wheezed, finally stopping.

“You didn’t say I couldn’t turn up the radio.”

“I implied it.”

“You implied nothing. You sang badly. I protected my ears. That’s called self-preservation.”

Leo slumped back in his seat, grinning. “Fine. New rule. No loopholes.”

“There are always loopholes,” I said.

“Then I’ll close them all.”

We passed a sign for a rest stop. Fifteen miles. The sky was getting gray, clouds stacking up like dirty laundry. Rain coming. I could feel it in the air, that heaviness before a storm.

“My turn again,” I said. “I dare you to make your dad laugh.”

Leo looked at his dad. Mr. Castellano looked back in the rearview mirror, expressionless.

“That’s impossible,” Leo said. “He hasn’t laughed since 2007.”

“I laughed last week,” Mr. Castellano said.

“At a dog falling off a couch. That’s not the same.”

“A laugh is a laugh.”

“No. A laugh at a dog falling off a couch is pity. Real laughter requires surprise. Wit. Timing.”

“So surprise me,” his dad said.

Leo sat up straight. He closed his eyes for a second, thinking. Then he opened them and said, perfectly deadpan, “Why don’t scientists trust atoms?”

“Because they make up everything,” Mr. Castellano said.

“You’ve heard that one.”

“Everyone’s heard that one.”

Leo tried another. “What do you call a fake noodle?”

“An impasta.”

“You’ve heard that one too?”

“It’s a classic.”

“Nothing is a classic. You’re just old.”

Mr. Castellano didn’t laugh. But the corner of his mouth twitched. That was something.

“I’m not laughing,” he said.

“Your face is laughing,” Leo said. “That counts.”

“My face is not laughing. My face is experiencing a mild muscle spasm.”

“That’s the most joy you’ve shown in a decade. I’m calling it a win.”

I watched them. There was something between Leo and his dad, a kind of comfortable war. They loved each other but they’d never say it. They showed it through insults and challenges and refusing to back down. I didn’t have that with my parents. We were nice to each other. We said the right things. But we never pushed. We never dared.

The rain started. Fat drops on the windshield, then more, then a sheet of water that made the world blur. Mr. Castellano slowed down, turned on the wipers. The sound was hypnotic. Swish. Thump. Swish. Thump.

“New dare,” Leo said, quieter now. “I dare you to tell me something you’ve never told anyone.”

The air in the car changed. Even Mr. Castellano seemed to hold his breath.

“That’s not a dare,” I said. “That’s a confession.”

“Same thing. You dare someone to tell the truth. Truth is the hardest thing to say.”

“I don’t have anything.”

“Everyone has something.”

I thought about it. The things I kept locked up. The small shames and the big ones. The way I felt when my parents fought behind closed doors. The way I pretended not to hear. The way I told myself I was fine when I wasn’t.

“I’m scared of the dark,” I said.

Leo tilted his head. “That’s not a secret. Everyone’s scared of the dark.”

“Not like this. Not the normal kind. I mean I can’t sleep without a light on. I mean I check under my bed every night. I’m eighteen years old and I still think something’s waiting in the shadows.”

He didn’t laugh. He didn’t make a joke. He just nodded.

“That’s real,” he said. “That counts.”

“Your turn.”

He looked out the window. The rain was coming harder now, the world smeared and gray. “I’m scared of becoming my dad.”

Mr. Castellano’s hands tightened on the wheel. He didn’t say anything.

“Not because he’s bad,” Leo said quickly. “He’s not. He’s good. He’s too good. He works a job he hates and he never complains. He takes care of everyone and nobody takes care of him. I’m scared I’ll do that. I’m scared I’ll wake up one day and realize I’ve spent my whole life being responsible and I forgot to be alive.”

The silence in the car was thick. Heavy. The kind of silence that means something.

Mr. Castellano pulled into the rest stop. He parked the car but didn’t turn off the engine. The wipers kept going. Swish. Thump. Swish. Thump.

“You won’t become me,” he said, his voice low. “Because you’re already braver than I ever was.”

Leo didn’t respond. He just stared at the rain on the window.

I looked at both of them. The father and the son. Two people who loved each other but couldn’t say it, so they said everything else instead.

And I realized I wasn’t just on a trip to the beach.

I was in the middle of something I didn’t understand yet.

The rain kept falling. The engine kept running. And somewhere ahead, the coast was waiting.



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