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

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

It wasn’t just the way Dad stared at old photos of Mom for too long.

It was the way his eyes softened whenever we saw couples holding hands in the park. The way he’d sit with a cup of coffee late at night, not drinking it, just… thinking. Like he was asking it for answers.

He missed her. A lot.

And even though he never said it, I knew he felt lonely.

But since he wouldn’t do anything about it, I decided I would.

I was only fourteen. Most people wouldn’t take me seriously. But I had something they didn’t: a plan. And a ring—well, technically it was a bottle cap I had bent into a circle. But hey, it worked.

Whenever we went out—to the store, a café, the park—I picked the nicest-looking woman around and dropped to one knee.

Will you marry my dad?” I’d ask, grinning like a hero from a movie.

Most of them laughed. Some played along.

Oh? What makes your dad so special, little man?” they’d ask.

I always answered with pride.

His name is Leo, and he’s kind, funny, and really smart. He takes great care of me. He’s super generous. And he makes the best lasagna. Plus, he always keeps his promises, especially the ones about ice cream.

That usually got a smile. Until the question that ruined everything.

And what does your wonder-dad do?

He’s a driver!” I’d reply, standing up straighter.

And boom—just like that, everything changed.

Their smiles dropped. Their eyes went dull. Some mumbled something polite before walking away. Others just turned and left.

What they didn’t know was that Dad wasn’t just any driver. He owned the company. He had his own team. He managed drivers, organized routes, did paperwork, and yes—he still drove sometimes because he said it helped him “stay grounded.”

But none of them stayed long enough to learn that.

One woman—the worst of them all—was a redhead I saw at the library.

She looked amazing, like her hair was fire made real. I thought she’d be perfect.

Nope.

A driver?” she sneered, raising an eyebrow. “Little boy, you think he’s good enough for me? Try again, kiddo.

Then she walked away like she hadn’t just crushed my heart and my dad’s chances of happiness.

That night at dinner, Dad sat across from me, barely touching his soup. He stirred it, quiet like always. I noticed he was still wearing his wedding ring.

I tapped my spoon against the table.

Dad?

He blinked, like I’d yanked him back from some deep thought.

Yeah, Cole? Are you okay?

Do you ever think about dating again?” I asked while buttering my roll.

He stiffened a little. Just a little. Then gave a tired smile and went back to his soup.

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 looked into his bowl like it could give him answers.

Your mom, Cole… She was everything. It’s hard to imagine anyone else. Once you find the greatest love of your life, you’ll understand.

I swallowed slowly.

Yeah. But Mom wouldn’t want you to be alone, Dad. And maybe… maybe it’s time to think about it. My music teacher is really nice. She plays the violin instead of the guitar, but I think we can look past that.

Dad chuckled. A real laugh.

I’m serious, Dad. Mom would want you to be happy.

That made him pause. His jaw tightened. Then he let out a slow breath.

I know.

For a long moment, we didn’t say anything. Just the soft clinks of spoons and plates.

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

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

But I did worry.

And I wasn’t giving up.


More Proposals, More Rejections

Next time we were grocery shopping, I spotted a woman in the produce aisle. She had a kind smile, was well-dressed, and was buying a watermelon—my favorite fruit. That had to mean something.

I’m going to the freezer section, son. Potatoes and onions, okay?” Dad said.

I nodded, waited a second, then bolted toward the woman. I dropped to one knee.

Will you marry my dad?

Oh my gosh, that is adorable!” she said.

I gave the usual speech about Dad being amazing.

What does he do?

He’s a driver.

And just like that—her face shut down.

Oh. Well… Good luck with that!

She left without another word.

Then came the next woman. Same story.

Your dad sounds sweet, but I’m looking for someone with more… stability.

He’s the most stable person I know,” I said, confused.

She smiled like I didn’t understand and walked away.

And finally, I realized: this wasn’t about love. It was about status.


The Gala That Changed Everything

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 families. Mom used to send snacks for those same people before she passed.

Dad was a guest speaker.

While he talked at the podium, I wandered around looking for a woman who might become my future stepmom.

And I thought I found her. She was laughing near the bar. Her smile felt warm, like a campfire on a cold night.

But before I could go over—

I saw her.

The redhead.

From the library.

The one who mocked me. Mocked Dad.

And there she was, standing next to him, batting her eyelashes and smiling like nothing ever happened.

No way. No. Nope.

I stormed over and yanked on Dad’s sleeve.

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

She gasped, hand to her chest.

Excuse me?

You don’t remember me? The library? I proposed.

Dad looked confused. “Proposed? Cole? What are you talking about?

The woman scoffed. “I don’t know what you’re talking about.

Really? You don’t remember me? Or him? The driver.

Recognition flickered in her eyes. Then instead of looking guilty, she smirked.

Oh, that? Kid, you made it sound like he was some cab driver. If I’d known who he really was, Leo…” she turned to him, her voice honey-sweet. “I would’ve answered differently.

She touched his arm.

Had I known you were a man of such… status, I would have—

Dad’s face darkened.

Before he could speak, I shouted, “I know who you should be with, Dad!

I pointed.

He followed my finger… and stopped cold.

Standing across the room was a woman with gentle eyes, wearing a soft blue dress. She turned and saw him—and smiled. Her laugh was familiar, comforting.

Wait!” she said to me. “You’re the young man who’s been proposing on your dad’s behalf? The ladies are all watching you.

Dad blinked.

It’s… you.

They had a history. A big one.

Her name was Billie.


A Past Reunited

I knew Billie years ago, Cole,” Dad explained.

They were once in love. But her father didn’t approve. Said my dad wasn’t good enough—too plain.

So they broke apart.

Now, Billie worked with the same kids my dad’s company helped. She was a donor, handled admin, and helped foster kids transition into real life.

I never thought I’d see you again, Billie,” Dad said.

She smiled. “And yet, here we are.

It wasn’t just a chance meeting.

It was fate.


The Best Crab Cakes Ever

Where are you going?” Dad asked me later.

Snack table. I heard the crab cakes are pretty good.

They laughed. Together.

That night, I saw something I hadn’t seen in years—my dad was happy.


Mint Ice Cream and the Truth

Later, we stopped for ice cream.

I had no idea you were proposing to strangers,” Dad laughed.

I just wanted to see who was out there. But they all walked away when I said you were a driver.

You didn’t tell them I owned the company?

You drive! That makes you a driver!

He shook his head, grinning.

Mint choc chip or just chocolate?

Mint, please. So… are you going to see Billie again?

He nodded slowly.

Yeah. But I want her to understand something. Your mom… she was the love of my life. Billie needs to know that before anything else.

I smiled, feeling full—heart, stomach, everything.

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


And somewhere, far away, I think Mom was smiling too.