Leo thinks his son, Cole, doesn’t notice his loneliness, but he does. Determined to find a wife for his widowed father, Cole tests potential partners with a simple proposition. Most fail. But at a charity gala, fate intervenes…
Dad thought I hadn’t noticed.
But I noticed it.
It was the way he lingered over 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 as if it could tell him what to do next.
He was alone.
A man looking at an album | Source: Midjourney
And since he didn’t want to do anything, I had to act.
So I took matters into my own hands.
With my special ring, an old bottle cap that I had bent into a perfect little circle, I had a plan.
Every time we went somewhere, I would find the prettiest woman in the room and propose to her. Since I’m fourteen, most of them thought it was adorable.
A bottle cap ring | Source: Midjourney
“Will you marry my father?” I asked, getting down on one knee with a smile.
Most of them laughed loudly. Some squatted down and made jokes.
“Oh? And what makes your father so special, little boy?”
“His name is Leo, he’s kind, funny, and very smart. He takes the best care of me. He’s endlessly generous. And he makes the best lasagna. Oh, and he always keeps his promises, especially if they involve ice cream.”
A tray of lasagna | Source: Midjourney
This usually got a smile from me, until the next question, and that’s when I lost a lot of them.
“And what does your wonderful dad do?”
“He’s a driver!” I replied proudly.
And that’s where things changed immediately. Of course, they assumed he was a posh businessman, a lawyer, or even a doctor.
A smiling boy | Source: Midjourney
But as soon as they learned he was a driver, their smiles faded. Their enthusiasm vanished. Some nodded politely and walked away. Others forced an embarrassed laugh before disappearing.
What I didn’t tell them is that my dad owned a trucking company. But he still drives. He loves it. He says it keeps him grounded, so he works extra hours during the week, in between all the administrative tasks. So, yes, technically, he’s a driver.
A man sitting in a vehicle | Source: Midjourney
But one woman, the worst of all, laughed right in my face. I thought she would have looked perfect with her red hair. It looked like she had fire shining on her head. But it turned out she wasn’t… so nice.
“A chauffeur? Little boy, you think he’s good enough for me?” she snickered, rolling her eyes at my dad’s picture. “Try again, kiddo. I’m sure there’s someone out there who wants to meet your dad. I’m not one of them.”
Then she walked away, further into the library, as if I were nothing. As if he were nothing.
A woman standing in a library | Source: Midjourney
That’s when I understood.
She definitely wasn’t the one.
A distraught little boy | Source: Midjourney
That evening, I sat across from my father, the best man I knew, as he absentmindedly stirred his soup.
He was silent, as he always was when he thought no one was paying attention to him. His wedding ring was still on his finger.
I banged my spoon against the table.
A bowl of soup | Source: Midjourney
“Dad ?”
He looked up, blinking as if I’d pulled him from somewhere deep in his mind.
“Yes, Cole? Are you okay?” he asked.
“Have you ever thought about dating someone else?” I asked, picking up a roll.
My father stiffened. Just for a second. Then he gave me a half-smile and went back to his soup.
A plate of rolls on a table | Source: Midjourney
“I don’t know, Cole. I’ve never really thought about it. And to be honest, it never seemed like an option.”
“Why not ?”
He sighed, swirling his spoon in the bowl.
“Your mother, 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, my son.”
A man sitting at a table | Source: Midjourney
I swallowed slowly.
“Yes. But Mom wouldn’t want you to be alone, Dad,” I replied. “And maybe it’s time you thought about it. My music teacher is very nice. But she likes playing the violin more than the guitar. I think we can get past that.”
My father looked up and smiled before bursting out laughing.
“I’m serious, Dad. Mom would never have wanted you to be alone.”
This made him think.
A man sitting at a table and laughing | Source: Midjourney
His jaw clenched as if he were fighting something, then he finally exhaled.
“I know.”
For a moment, neither of us spoke. The only sound was the quiet clinking of silverware.
Then he looked up, his eyes warm but sad.
“You don’t need to worry about me, kiddo,” he said. “I’ll be fine, Cole.”
A boy sitting at a table | Source: Midjourney
But I was worried. And I wasn’t going to stop now.
The next time we went grocery shopping, I spotted a woman near the produce aisle. She looked 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.”
A woman standing in a supermarket | Source: Midjourney
I ran to the woman, knelt down, and held out my bottle cap ring.
“Will you marry my father?” I asked.
“Oh my God, that’s adorable,” she exclaimed.
“His name is Leo, he’s kind, funny, and very intelligent. He takes the greatest care of me. He’s generous beyond belief, and…”
She burst out
A boy in a supermarket | Source: Midjourney
“That sounds great! What’s he doing?” she asked.
“My father is a driver.”
His face froze.
“Oh,” she said quickly, sitting up. “I… um. Well, good luck!”
And just like that, she was gone.
A woman in a supermarket | Source: Midjourney
The next woman was even worse.
“Your dad seems great, but I’m really looking for someone with a little more… stability,” she said, putting on a fake smile.
“She’s the most stable person I know,” I said, not quite understanding what she meant.
She simply patted me on the shoulder like I was a silly child and walked away. I clenched my fists, finally understanding that this was the way the world was.
A woman standing in a park | Source: Midjourney
It wasn’t about love or finding someone to live with, it was about status.
A few weeks later, my dad took me to a charity event.
We were invited because my father’s company provides free transportation for foster children, sick veterans, and sometimes low-income workers. He was invited because he made a real difference. When my mother was alive, she would also send snacks for these people.
A charity gala setting | Source: Midjourney
He had been invited as a speaker, and while he stood at the podium, I wandered around the room, looking for a potential future mother-in-law.
And for a moment, I thought I saw her. The right one.
She was laughing with someone near the bar, her smile warm, her presence different from the others. But before I could move forward, my stomach dropped.
A smiling man standing in front of a podium | Source: Midjourney
Because across the room, standing next to my dad, it was her .
The redhead from the library weeks ago.
This was the same woman who had laughed at me, rolled her eyes at my father’s picture and grimaced when she learned he was a chauffeur. The same woman who had treated us as if we were beneath her.
And now ?
A smiling woman | Source: Midjourney
Now she’s flirting with him.
No, no way.
I rushed over, grabbed my father’s sleeve, and pulled his arm.
“Dad, stop. She’s not the one,” I said. “Don’t even waste your time talking to her.”
An upset boy | Source: Midjourney
The woman gasped, putting a hand to her chest as if she was so offended.
“Excuse me ?”
“Seriously? Don’t you remember me from the library? I asked you to marry my father.”
My father looked desperately confused.
“Proposed to me? Cole? What’s this?” he asked, frowning.
“I don’t know what you’re talking about!” the woman said, ignoring my father.
A woman standing with her arms crossed | Source: Midjourney
“Really? You don’t remember me? You don’t remember my dad? The driver.”
She hesitated for a moment before the memory dawned on her face.
Then, instead of looking guilty, she scoffed.
“Oh, that? Please. Kid, you made it look like he was a taxi driver or something. If I’d known who you really were, Leo…” she said, turning to Dad. “I would have answered differently.”
An upset boy | Source: Midjourney
Her voice was different now. Softer. As if she had just discovered something precious.
She placed a hand on my father’s arm, her long eyelashes fluttering as if she were about to fly away.
“I mean, really, Leo. If I had known you were a man of such… status, I would have…”
Dad’s face darkened.
I interrupted him before he could open his mouth.
A redhead at a gala | Source: Midjourney
“I know who you should be with, Dad!” I said.
Then I pointed.
My father followed my gaze and froze. His grip on my hand tightened. His expression changed.
Confusion. Shock. Something deeper too.
“Dad?” I frowned, confused.
Then she turned around. Her eyes fell on my father and widened.
A smiling woman | Source: Midjourney
And she laughed. Not in a horrible way like the redhead had laughed, but warmly, like my mother had always laughed.
“Wait! Are you the young man who advertised for your father?” she teased, shaking her head amusedly. “All the ladies are waiting to be approached by you.”
My father still hadn’t said a word. His mouth opened slightly, but nothing came out.
Finally, he exhaled. “It’s… you.”
A smiling man | Source: Midjourney
I had never seen him like this, as if his whole world had just turned upside down.
It turns out there was a lot more going on between my father and this woman.
“I knew Billie years ago, Cole,” he explains.
At the time, they were inseparable. They had dreams, plans, and promises. But life had other ideas.
A young couple | Source: Midjourney
His father disapproved of my father. He thought Dad wasn’t good enough, too simple, too ordinary.
That’s how they were separated. Billie was at the charity gala because she was a longtime donor. She worked with at-risk children and helped them transition out of the foster care system. She also did a lot of their administration. The same children my father’s company helps.
A woman using a laptop | Source: Midjourney
“I never thought I’d see you again, Billie,” my father said.
“And yet, somehow, here we are,” she said, smiling a little.
She looked sad. And hopeful, too.
“It’s been decades, Leo,” she said. “I knew someone named ‘Leo’ helped children, but I never expected it to be you. Until tonight.”
“Well, I guess my work here is done,” I said.
“Where are you going? There are still a few speeches left before we can leave, son.”
A smiling boy | Source: Midjourney
“I’ll be at the snack table,” I said. “I heard the crab cakes are pretty good.”
They laughed together.
That night was not just a meeting.
It was the beginning of something new. And for the first time in a long, long time, I saw my father truly happy.
A tray of food | Source: Midjourney
Later, as Dad and I went to get ice cream before heading home, he turned to me and smiled.
“I didn’t know you were trying to advertise me,” he said, laughing. “And propose to people?”
“I just wanted to see who wanted you,” I confessed. “But a lot of people turned away after learning you were a driver.”
An ice cream freezer | Source: Midjourney
“So you didn’t tell them I owned a trucking company?” my dad chuckled.
“Well, you’re the one driving the vehicles!” I exclaimed. “That makes you a chauffeur!”
“Mint chip ice cream or just chocolate?” he asked me.
“Mint, please. So, are you going to see Billie again?” I asked back.
A boy holding an ice cream cone | Source: Midjourney
“Cole, relax,” he said, but he was smiling. “I’ll see her, of course. But we have a lot of history. And I loved her once. But your mother was the love of my life, so I need Billie to understand that before I even consider anything else.”
I nodded.
“I’m just glad you thought about it,” I said.
Close-up of a smiling boy | Source: Midjourney
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This work is inspired by real events and people, but has been fictionalized for creative purposes. Names, characters, and details have been changed to protect privacy and enhance the story. Any resemblance to real persons, living or dead, or to actual events is purely coincidental and not intended by the author.
The author and publisher make no claims regarding the accuracy of events or character portrayals and are not responsible for any misinterpretations. This story is provided “as is,” and all opinions expressed are those of the characters and do not reflect the opinions of the author or publisher.
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