I Wanted to Find a Wife for My Widowed Dad and Tested Them – Only One Passed

Share this:

Dad Thought I Didn’t Notice. But I Did.

It was in the way he sat quietly at night, holding his coffee like it held answers. The way his eyes softened when we passed couples holding hands in the park. The way he stared at the old photos of Mom, his thumb gently brushing over her smile like he could feel her through the glass.

Yeah. I noticed.

He missed her. He was lonely. And even though he pretended he was fine, I could see through it. He’d smile at me and say, “Everything’s good, buddy,” but the sadness was still there, hidden in his quiet moments.

So I made up my mind.

If he wasn’t going to do anything about it, I would.

I was fourteen and completely serious about my mission: find my dad a wife.

And I had a plan.

I took an old bottle cap and bent it into a perfect circle. It was my special ring—my secret weapon. Every time we went out, I looked for the nicest, prettiest woman in the room, dropped to one knee, and popped the question.

Not for me. For him.

Will you marry my dad?” I’d say with my biggest, brightest grin.

Most of them laughed. Some even crouched down and played along.

“Oh really? And what makes your dad so special, little man?”

I had my answer ready every time. “His name is Leo. He’s kind, really funny, and super smart. He takes great care of me. He makes the best lasagna, and he always keeps his promises—especially if they involve ice cream!”

That usually got a giggle. But then came the question that ruined everything.

“And what does your amazing dad do?”

I’d puff up proudly. “He’s a driver!”

And just like that, their smiles faded.

Some nodded politely and drifted away. Others laughed awkwardly and made up an excuse to leave. They probably imagined he was just some random cab driver. What they didn’t know was that my dad owned the entire transportation company. He just loved to drive, said it kept him grounded.

But they didn’t stick around long enough to find that out.

One woman—probably the worst of the bunch—looked me up and down and scoffed right in my face. She had fire-red hair that shimmered like sunlight, and for a second, I thought she could be the one.

I was wrong.

“A driver? Little boy, you think he’s good enough for me?” she sneered, her nose wrinkling like she smelled something bad. “Try again, kiddo. I’m sure someone out there wants your dad. But it’s not me.”

Then she just turned and walked away into the library like we didn’t matter at all.

That night, I sat across from my dad at the dinner table. He was stirring his soup slowly, eyes staring through the steam like he was somewhere else. His wedding band was still on his finger. He never took it off.

I tapped my spoon gently on the table.

“Dad?”

He looked up, blinking like I’d pulled him out of a dream. “Yeah, Cole? You okay?”

I nodded and bit my lip. “Do you ever think about… dating again?”

He froze. Just for a second. Then smiled halfway and stirred his soup again.

“I don’t know, Cole. I never really thought about it. And if I’m being honest, it never really seemed like an option.”

“Why not?”

He sighed. “Your mom was everything to me. It’s hard to imagine anyone else. When you find the greatest love of your life… you’ll understand.”

I swallowed hard. “But Mom wouldn’t want you to be alone, Dad. Maybe it’s time you think about it. My music teacher’s really nice! She plays violin instead of guitar, but we can overlook that, right?”

He burst out laughing, and for a second, I saw a glimpse of the old Dad. The happy one.

“I’m serious, Dad. Mom wouldn’t want you to be alone.”

He got quiet again, his jaw clenching a little before he exhaled.

“I know.”

Then he looked at me, his eyes soft but sad.

“You don’t need to worry about me, kiddo. I’ll be just fine.”

But I did worry.

And I wasn’t giving up.


The next time we went grocery shopping, I saw her. A woman in the produce aisle with a bright smile, wearing a cute blue dress. She was picking out a watermelon—my favorite fruit. It had to be a sign.

“I’m heading to the freezer section,” Dad said. “Grab some potatoes and onions, alright?”

“Sure!” I said. But I had another plan.

I rushed over, got down on one knee, and held up my bottle cap ring.

“Will you marry my dad?”

She laughed in surprise. “Oh my gosh, that is adorable!”

“His name’s Leo. He’s kind, funny, and smart. He’s generous and makes amazing lasagna!”

She giggled. “Wow! What does he do?”

“He’s a driver!”

Her face froze. “Oh… um, well, good luck with that!” she said, standing up straight and walking away quickly.

Strike one.

A week later, another woman told me, “Your dad sounds great, but I’m really looking for someone with more… stability.”

I didn’t fully get it at first. “He’s the most stable person I know,” I said, confused.

She gave me a tight smile, patted my shoulder like I was a kid playing pretend, and walked off.

I clenched my fists.

This wasn’t about love. Not really. It was about money, jobs, and how people looked on paper.


Then came the charity gala.

My dad’s company was being honored for offering free transportation to foster kids, sick veterans, and people in need. He’d even been invited to give a speech. Mom used to help too—she’d bake cookies and send snacks with him when he did those rides.

While Dad went up to the stage, I wandered around. That’s when I saw her.

A woman laughing near the bar, her smile lighting up the whole room. Something about her just felt… real.

But before I could get to her, I spotted someone else—her.

The redhead from the library.

The woman who’d sneered at my proposal and acted like Dad wasn’t good enough.

Now she was standing next to him, smiling and flirting like she just discovered he was rich or famous.

My chest burned.

I marched straight over and tugged my dad’s sleeve.

“Dad, stop. She’s not the one. Don’t waste your time.”

The woman gasped, clutching her chest like I’d insulted her.

“Excuse me?”

“You don’t remember me from the library? I proposed,” I said.

Dad looked totally lost. “Proposed? Cole, what—?”

“I don’t know what this kid is talking about!” she snapped.

“Really? You don’t remember me? The ring? The ‘driver’?” I stared at her.

Then it hit her. She remembered. But instead of saying sorry, she scoffed.

“Oh, that? Please. Kid, you made it sound like he was some cab driver. Had I known who he really was, well…”

She turned to my dad with a syrupy voice. “Leo, if I had any idea you were such a man of… status… I would have said something else.”

She fluttered her lashes and touched his arm.

I had never seen my dad’s face turn so cold.

“I know who you should be with, Dad!” I said, pointing across the room.

He turned—and froze.

There she was. The woman from earlier.

She noticed us and walked over, smiling.

“You must be the famous son who’s been proposing to strangers for his dad,” she teased. “All the women are waiting to be picked!”

Dad stared. “It’s… you.”

She blinked. “Leo?”

Turns out, they knew each other.

Her name was Billie, and she and Dad had been close—very close—many years ago. They were in love, had plans, dreams. But her father didn’t approve. He thought my dad wasn’t good enough. Too simple.

They had been torn apart.

But now? Here they were again. At the same gala. Helping the same kids.

“I never thought I’d see you again,” my dad said softly.

“And yet, here we are,” Billie replied, her voice warm and full of old memories.


Later that night, we sat on a bench eating ice cream.

Dad smiled at me. “So… you’ve been advertising me?”

I shrugged. “Just wanted to find someone worthy of you. A lot of people turned away when they heard you were a driver.”

He chuckled. “You never told them I owned the company?”

“You drive, so… you’re a driver!” I said proudly.

“Mint chocolate chip or plain chocolate?”

“Mint, always. So… are you going to see Billie again?”

He looked thoughtful. “I think I will. But it’s not simple, Cole. We have history. And I loved your mom deeply. Billie would need to understand that before anything happens.”

I nodded, my chest warm.

“I’m just glad you’re thinking about it.”

And that night, as I watched my dad smile in a way I hadn’t seen in years, I knew something had changed.

Maybe love takes time. Maybe fate just needs a little help.

And maybe… sometimes a bent bottle cap can change everything.