Dad thought I didn’t notice.
But I did. Oh, I really did.
It was in the way he stared at old pictures of Mom, his eyes going soft like he was in another world. It was in the way he’d stop and smile quietly when he saw older couples holding hands in the park. And most of all, it was the way he’d sit at the kitchen table late at night, just staring into his coffee, like he was waiting for it to give him answers.
My dad was lonely.
And if he wasn’t going to do anything about it, then I would.
I had a plan.
It wasn’t complicated. It started with a ring — not a real one, of course. Just an old bottle cap I had bent into a perfect little circle. But to me, it was powerful. Magical, even. Because with that ring, I was going to find my dad a wife.
Everywhere we went — the grocery store, the dentist’s office, the bank, you name it — I kept my eyes open. I looked for someone who looked nice, kind, and maybe just a little bit like they believed in happy endings. And once I found her?
I’d get down on one knee, flash my bottle-cap ring, and say the same line every time:
“Will you marry my dad?”
Now, I’m fourteen. Most women thought it was funny or sweet. They’d laugh, sometimes play along.
“Oh? And what makes your dad so special, little Romeo?”
And I’d say, proud as anything:
“His name is Leo. He’s kind, funny, super smart, and he makes the best lasagna in the world. He takes care of me like no one else. He’s generous. And he always keeps his promises — especially the ones that involve ice cream.”
That usually got a few smiles.
But then came the deal-breaker. The question that turned everything upside down.
“So what does your amazing dad do?”
I always answered proudly:
“He’s a driver!”
And just like that… everything changed.
Their smiles? Gone. Their interest? Vanished. Like someone popped a balloon.
Most would nod politely and say something like, “That’s… nice,” before walking away.
What they didn’t know — what I didn’t tell them — was that my dad owns a whole transportation company. He runs the place. But yeah, he still drives sometimes. He says it keeps him grounded. Makes him feel connected to people.
But none of that mattered once they heard the word “driver.”
And the worst one of all? Oh, she was unforgettable.
She had the brightest red hair I’d ever seen. Like her head was on fire — in a cool way. I really thought she was the one. She looked fancy, confident, like someone who belonged in a magazine.
But when I asked her?
She didn’t just say no.
She sneered. Right at me.
“A driver? Little boy, you think he’s good enough for me?” she said, wrinkling her nose. “Try again, kiddo.”
Then she turned and walked away, like I was invisible. Like he was invisible.
That night, I watched my dad stir his soup in silence. He always got quiet when he thought no one was watching. His wedding band still sat on his finger, shining under the kitchen light.
I tapped my spoon on the table.
“Dad?”
He looked up, surprised, like I’d pulled him out of a daydream.
“Yeah, Cole? Everything okay?”
“Do you ever think about dating again?” I asked, ripping a piece of bread.
He froze for a second. Then smiled — but only a little — and looked back down.
“I don’t know, Cole. I haven’t really thought about it. And… it just doesn’t seem like an option.”
“Why not?”
He sighed.
“Because of your mom. She was everything. It’s hard to imagine someone else. One day, when you find the kind of love we had, you’ll understand.”
I swallowed.
“Yeah. But Mom wouldn’t want you to be alone, Dad. I know she wouldn’t. Maybe it’s time.” I smiled. “My music teacher is nice. She plays the violin, not the guitar, but I think we can work with that.”
My dad burst out laughing.
“You’re serious?”
“Very serious.” I nodded. “Mom wouldn’t want you to be sad forever.”
He got quiet again. His face tensed, like he was thinking about something hard.
Then he let out a slow breath.
“I know, son.”
But I could tell — he wasn’t ready.
Still, I wasn’t giving up.
Next time we went to the grocery store, I saw her. By the watermelons. She had a bright smile, nice hair, and she was picking out my favorite fruit. It felt like fate.
“I’m going to the freezers,” Dad said. “Get us some potatoes and onions.”
“Got it!” I said — and dashed away.
I ran right up to the woman, dropped to one knee, and offered my trusty bottle-cap ring.
“Will you marry my dad?”
She laughed.
“Oh my gosh, that is adorable!”
“His name is Leo. He’s kind, funny, smart. Makes the best lasagna and loves ice cream almost as much as I do.”
She smiled big — until she asked:
“And what does he do?”
“He’s a driver.”
Her face froze.
“Oh,” she said. Then she stepped back. “Well, good luck with that!”
She vanished before I could say anything else.
And the next woman?
Even worse.
“Your dad sounds lovely, but I’m looking for someone with more… stability,” she said with a plastic smile.
“He’s the most stable person I know,” I said. But she was already gone.
I was starting to get it.
To a lot of people, love didn’t matter.
Status mattered.
A few weeks later, Dad took me to a charity gala. We were invited because his company helps transport foster kids, sick veterans, and low-income workers. People always thank him, but my mom was part of it, too. She used to bake cookies and pack snacks for the drivers.
Dad was a guest speaker that night, and while he was up at the podium, I wandered the crowd. I scanned the room for “The One.”
And I saw her.
She was standing near the bar, laughing. Her whole presence felt different — soft, warm, genuine.
But just when I was about to head over, I saw someone else.
Her.
The redhead. The one who laughed at me. Who acted like we weren’t good enough.
And now? Now she was next to my dad, smiling like they were old friends.
I stormed over and grabbed his sleeve.
“Dad, stop. She’s not the one. Don’t even talk to her.”
She gasped, putting a hand on her chest.
“Excuse me?”
“You don’t remember me? From the library? I proposed to you!”
Dad looked confused.
“Proposed? Cole? What are you talking about?”
“You really don’t remember? I told you about my dad. You said he wasn’t good enough!”
Recognition flashed in her eyes.
But she didn’t look embarrassed.
She scoffed.
“Oh, that? Please. Kid, you made it sound like he was some cab driver. If I had known he owned the company… Leo,” she purred, turning to my dad, “I would’ve answered differently.”
She reached for his arm. Her voice went soft, sugary.
But Dad’s face turned stone cold.
Before he could say anything, I pointed across the room.
“I know who you should be talking to.”
He turned. His eyes locked onto her.
The woman by the bar.
His hand tightened in mine.
He froze.
And then she turned and saw him.
She smiled. Not like the others. It was real. Warm.
“Wait a minute! Are you the famous son that’s been advertising your dad?” she laughed. “I’ve heard all about you. The ladies were hoping to be next!”
My dad blinked.
Then whispered, like his voice had been lost for years:
“It’s… you.”
Later, he told me everything.
Her name was Billie. They had been young and in love once. But her father thought my dad wasn’t good enough. He made her choose.
So they were torn apart.
Billie never married. She spent her time helping foster kids transition into homes. The very same kids Dad’s company helped.
“I never thought I’d see you again,” Dad told her.
“And yet, here we are,” she said, smiling sadly.
That night wasn’t just about speeches or donations.
It was about second chances.
And for the first time in years, I saw something new on Dad’s face.
Hope.
Later, as we stopped for ice cream, he nudged me.
“So you’ve been proposing to people, huh?”
“Just trying to help,” I said. “A lot of them didn’t like that you’re a driver.”
“You didn’t tell them I owned the company?” he laughed.
“You still drive!” I argued. “That makes you a driver!”
He chuckled. “Mint or chocolate?”
“Mint. Are you going to see Billie again?”
He paused.
“I think so, yeah. But I’ll be honest with her. Your mom was the love of my life. Billie needs to understand that before anything else.”
I nodded.
“I just want you to be happy, Dad.”
He smiled, then put an arm around my shoulders.
“Me too, son. Me too.”
And maybe… just maybe… we were finally on our way.
