I Wanted to Find a Wife for My Widowed Dad and Tested Them – Only One Passed #8

Leo thinks his son, Cole, doesn’t notice his loneliness, but he does. Determined to find his widowed dad a wife, Cole tests potential matches with a simple proposal. Most fail. But at a charity gala, fate steps in…

Dad thought I didn’t notice.

But I did.

It was the way he lingered on old photos of Mom, the way his eyes softened when he saw happy couples holding hands in the park, the way he sighed at night, staring into his coffee like it could tell him what to do next.

He was lonely.

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

So, I took matters into my own hands.

With my special ring, an old bottle cap I had bent into a perfect little circle, I had a plan.

Every time we went somewhere, I found the prettiest woman in the room and proposed. Now, I’m fourteen, so most of them thought it was adorable.

“Will you marry my dad?” I’d ask, dropping to one knee with a grin.

Most of them laughed loudly. Some crouched down and humored me.

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

“His name is Leo, and he’s kind, funny, and really smart. He takes the best care of me. He’s generous beyond anything. And he makes the best lasagna. Oh, and he always keeps his promises, especially if they involve ice cream.”

That usually got a smile, until the next question, which is where I lost a lot of them.

“And what does your wonder-dad do?”

“He’s a driver!” I’d say proudly.

And that’s when things would change immediately. Of course, they’d assume that he was a fancy businessman, a lawyer, or even a doctor.

But the moment they heard that he was a driver, their smiles faded. Their enthusiasm drained like a popped balloon. Some nodded politely and walked away. Others forced an awkward laugh before disappearing.

What I didn’t tell them was that my dad owned a driving company. But he still drives. He loves it. He says it keeps him grounded, so he takes on shifts during the week in between all the admin. So, yeah, technically, he’s a driver.

But one woman, the worst one of them all, scoffed right in my face. I thought that she would have been perfect with her red hair. It looked like she had fire shining brightly on her head. But it turned out that she was… not so nice.

“A driver? Little boy, you think he’s good enough for me?” she sneered, rolling her eyes at my dad’s picture. “Try again, kiddo. I’m sure there’s someone out there who’s keen to meet your father. I’m not one of them.”

Then she walked away, further into the library, like I was nothing. Like he was nothing.

That’s when I knew.

She definitely wasn’t the one.

That night, I sat across from my dad, the best man I knew, as he stirred his soup absentmindedly.

He was quiet, the way he always got when he thought no one was paying attention. His wedding band was still on his finger.

I tapped my spoon against the table.

“Dad?”

He looked up, blinking like I’d pulled him from somewhere deep inside his mind.

“Yeah, Cole? Are you okay?” he asked.

“Do you ever think about dating again?” I asked, picking up a dinner roll.

My dad stiffened. Just for a second. Then he gave me a half-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 sighed, swirling his spoon in the bowl.

“Your mom, Cole,” he said. “She was everything. It’s hard to imagine anyone else, you know? Once you find the greatest love of your life, you’ll understand, son.”

I swallowed slowly.

“Yeah. But Mom wouldn’t want you to be alone, Dad,” I pushed. “And maybe it’s time you thought about it. My music teacher is really nice. But she likes to play the violin instead of the guitar. I think we can look past that.”

My father looked up and smiled before bursting into laughter.

“I’m serious, Dad. Mom would never want you to be alone.”

That made him pause.

His jaw tensed like he was fighting something, then he finally exhaled.

“I know.”

For a moment, neither of us spoke. The only sound was the quiet clink of silverware.

Then, he looked up, eyes warm but sad.

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

But I did worry. And I wasn’t stopping now.

The next time we went grocery shopping, I spotted a woman near the fresh produce aisle. She seemed perfect.

Pretty, well-dressed, a friendly smile, and she was buying a watermelon, my favorite fruit.

“I’m going to the freezers, son,” Dad said. “You go get us some potatoes and onions.”

I ran up to the woman, dropped to one knee, and held out my bottle-cap ring.

“Will you marry my dad?” I asked.

“Oh my gosh, that is adorable,” she gasped.

“His name is Leo, and he’s kind, funny, and really smart. He takes the best care of me. He’s generous beyond anything, and…”

She laughed out loud.

“That sounds amazing! What does he do?” she asked.

“My dad is a driver.”

Her face froze.

“Oh,” she said quickly, standing up straight. “I… um. Well, good luck with that!”

And just like that, she was gone.

The next woman was even worse.

“Your dad sounds great, but I’m really looking for someone with a little more… stability,” she said, flashing a fake smile.

“He’s the most stable person I know,” I said, not fully understanding what she meant.

She just patted my shoulder like I was some dumb little kid and walked away. I clenched my fists, finally realizing the way of the world.

This wasn’t about love or finding someone to be with, this was all about status.

A few weeks later, my dad took me to a charity event.

We were invited because my dad’s company helps provide free transportation for kids in foster care, sick veterans, and sometimes, low-income workers. He was invited because he’s made a real difference. When my mom was alive, she used to send snacks for those people, too.

He had been invited as a guest speaker, and while he stood at the podium, I wandered around the room, looking for a potential future stepmom.

And for a moment, I thought I saw her. The one.

She was laughing with someone near the bar, her smile warm, her presence different from the others. But before I could go over, my stomach dropped.

Because across the room, standing beside my dad, was her.

The redhead from the library weeks before.

It was the same woman who had laughed at me, who had rolled her eyes at my dad’s picture and grimaced when she found out that he was a driver. The same woman who had treated us like we were beneath her.

And now?

Now she was flirting with him.

No. No way.

I stormed over, grabbed my dad’s sleeve, and yanked his arm.

“Dad, stop. She’s not the one,” I said. “Don’t even waste your time talking to her.”

The woman gasped, putting a hand to her chest like she was so offended.

“Excuse me?”

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

My father looked hopelessly confused.

“Proposed? Cole? What on earth?” he asked, frowning.

“I don’t know what you’re talking about!” the woman said, ignoring my dad.

“Really? You don’t remember me? You don’t remember my dad? The driver.”

She hesitated for a moment before recognition flickered across her face.

Then, instead of looking guilty, she scoffed.

“Oh, that? Please. Kid, you made it sound like he was some cab driver or something. Had I known who you really were, Leo…” she said, turning to Dad. “I would have answered differently.”

Her voice was different now. Smoother. Sweeter. Like she had just discovered something valuable.

She placed a hand on my dad’s arm, her long eyelashes fluttering like she was going to take off.

“I mean, really, Leo. Had I known you were a man of such… status, I would have…”

Dad’s face darkened.

I cut in before he could even open his mouth.

“I know who you should be with, Dad!” I said.

Then, I pointed.

My dad followed my gaze, and he froze. His grip on my hand tightened. His expression shifted.

Confusion. Shock. Something deeper, too.

“Dad?” I frowned, confused.

Then, she turned. Her eyes landed on my dad and widened.

And she laughed. Not in a horrible way like the redhead had laughed, but warmly, like my mother had always laughed.

“Wait! You’re the young man who’s been advertising your dad?” she teased, shaking her head in amusement. “All the ladies are waiting to be approached by you.”

My dad still hadn’t said a word. His mouth opened slightly, but nothing came out.

Finally, he exhaled. “It’s… you.”

I had never seen him look like that, like his entire world had just shifted.

It turns out that there had been a lot more to my dad and the woman.

“I knew Billie years ago, Cole,” he explained.

Back then, they had been inseparable. They had dreams, plans, and promises. But life had other ideas.

And so, they had been forced apart. Now, Billie was at the charity gala because she was a long-time donor, working with at-risk kids, helping them transition out of the foster system. She did a lot of their admin, too. The same kids that my dad’s company helps.

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

“And yet, somehow, here we are,” she said, smiling a little.

She seemed sad. And hopeful, too.

“It’s been decades, Leo,” she said. “I knew that someone named ‘Leo’ was helping the kids, but I didn’t expect it to be you. Until tonight.”

“Well, I guess my job here is done,” I said.

“Where are you going? There’s still a few speeches left before we can leave, son.”

“I’ll be at the snack table,” I said. “I heard that the crab cakes are pretty good.”

They laughed, together.

That night wasn’t just a reunion.

It was the beginning of something new. And for the first time in a long, long time, I saw my dad truly happy.

Later, when Dad and I were getting some ice cream before heading home, he turned to me and smiled.

“I had no idea that you were trying to advertise me,” he laughed. “And proposing to people?”

“I just wanted to see who was out there,” I confessed. “But a lot of people turned away after hearing that you were a driver.”

“So, you didn’t tell them that I was the owner of a transportation company?” my dad chuckled.

“Well, you drive the vehicles!” I exclaimed. “That makes you a driver!”

“Mint choc chip or just plain chocolate ice cream?” he asked me.

“Mint, please. So, are you going to see Billie again?” I asked.

“Cole, relax,” he said, but he was smiling. “I’m going to see her, sure. But we do have a lot of history. And I did love her once. But your mother was the love of my life, so I need Billie to understand that before we even consider anything else.”

I nodded.

“I’m just happy that you’re thinking about it,” I said.

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When Anna’s dad leaves her a beautifully wrapped Christmas gift with strict instructions not to open it until morning, she never expects her scheming stepmother, Melanie, to tear into it first. But Melanie’s greed triggers a chain of events she never saw coming… How about some karma for Christmas?

This work is inspired by real events and people, but it has been fictionalized for creative purposes. Names, characters, and details have been changed to protect privacy and enhance the narrative. Any resemblance to actual persons, living or dead, or actual events is purely coincidental and not intended by the author.

The author and publisher make no claims to the accuracy of events or the portrayal of characters and are not liable for any misinterpretation. This story is provided “as is,” and any opinions expressed are those of the characters and do not reflect the views of the author or publisher.