My dad thought I was unaware of his loneliness. But I noticed. Determined to find my widowed dad a wife, I test potential matches with a simple proposal. Most fail. But at a charity gala, fate steps in…
I always knew my dad, Leo, was lonely.
It was in the way he lingered on old photos of Mom, the softness in his eyes when he saw couples holding hands in the park, the deep sighs he let out at night as he stared into his coffee, as if it held the answers he sought.
He was lonely.
And since he wouldn’t do anything about it, I decided I would.
So, I came up with a plan.
Armed with my special ring—a bottle cap I had bent into a perfect little circle—I took action. Every time we went out, I found the prettiest woman in the room and proposed. At fourteen, most people found it adorable.
“Will you marry my dad?” I’d ask, dropping to one knee with a grin.
Most women laughed. Some crouched down to play along.
“Oh? And what makes your dad so special, little boy?”
“His name is Leo, and he’s kind, funny, and really smart. He takes great care of me. He’s incredibly generous, and he makes the best lasagna. Oh, and he always keeps his promises, especially when they involve ice cream.”
That usually earned me a smile—until the next question came up.
“And what does your amazing dad do?”
“He’s a driver!” I’d say proudly.
That’s when everything changed. They had assumed he was a businessman, a lawyer, maybe even a doctor. But when they heard “driver,” their enthusiasm vanished. Some offered polite nods before walking away. Others forced an awkward laugh before disappearing.
What they didn’t know was that my dad owned a transportation company. He still drove because he loved it—it kept him grounded. But technically, yes, he was a driver.
One woman, the worst of them all, scoffed in my face. I had thought she would be perfect, with her striking red hair that shone like fire. But her personality was anything but warm.
“A driver? Little boy, you think he’s good enough for me?” she sneered, rolling her eyes at Dad’s picture. “Try again, kiddo. I’m sure someone else will be interested in your father. I’m not one of them.”
She turned and walked deeper into the library, as if Dad and I were nothing.
That’s when I knew.
She definitely wasn’t the one.
That night, sitting across from my dad, I watched him stir his soup absentmindedly. He was quiet, lost in thought, his wedding band still on his finger.
I tapped my spoon against the table.
“Dad?”
He looked up, blinking as if pulled from deep within his mind. “Yeah, Cole? You okay?”
“Do you ever think about dating again?”
He stiffened, just for a second, before offering a small smile and returning to his soup.
“I don’t know, Cole. I never really thought about it. Honestly, it never seemed like an option.”
“Why not?”
He sighed, swirling his spoon through the broth.
“Your mom, Cole. She was everything. It’s hard to imagine anyone else, you know? Once you find the greatest love of your life, you’ll understand.”
I swallowed. “Yeah. But Mom wouldn’t want you to be alone, Dad,” I pressed. “Maybe it’s time you thought about it. My music teacher is really nice. She plays the violin instead of the guitar, but I think we can overlook that.”
Dad chuckled, then burst into laughter.
“I’m serious, Dad. Mom wouldn’t want you to be alone.”
He paused, his jaw tightening before he exhaled. “I know.”
For a moment, we sat in silence, the quiet clink of silverware filling the space. Then he looked up, his eyes warm but sad.
“You don’t need to worry about me, kiddo. I’ll be just fine.”
But I did worry. And I wasn’t stopping now.
At the grocery store, I spotted a woman in the produce aisle—pretty, well-dressed, smiling, and picking out a watermelon, my favorite fruit.
While Dad headed to the freezer section, I ran over, dropped to one knee, and held out my bottle-cap ring.
“Will you marry my dad?”
She gasped. “Oh my gosh, that is adorable.”
“His name is Leo, and he’s kind, funny, and really smart. He takes great care of me…”
She laughed, entertained. “That sounds amazing! What does he do?”
“My dad is a driver.”
Her face froze.
“Oh,” she said, straightening. “I… um. Well, good luck with that!” And just like that, she was gone.
Another woman was worse.
“Your dad sounds great, but I’m looking for someone with a little more… stability,” she said with a forced smile.
“He’s the most stable person I know,” I argued, confused.
She patted my shoulder as if I were a naive child and walked away. That’s when I realized—this wasn’t about love. It was about status.
A few weeks later, we attended a charity gala. Dad’s company provided free transportation for foster children, sick veterans, and low-income workers. He was invited as a guest speaker.
While Dad spoke at the podium, I searched the room for potential stepmoms. I thought I spotted someone—the one. She was laughing warmly near the bar. But before I could approach, my stomach dropped.
Across the room, beside Dad, stood her.
The redhead from the library.
She, who had sneered at Dad’s picture and scoffed at the idea of a driver, was now flirting with him.
No way.
I stormed over, grabbed Dad’s sleeve, and tugged.
“Dad, stop. She’s not the one.”
The woman gasped, feigning offense. “Excuse me?”
“Seriously? You don’t remember me from the library? I proposed.”
Dad frowned. “Proposed? Cole, what are you talking about?”
The woman scoffed. “Oh, that? Kid, you made it sound like he was some cab driver. If I had known who he really was…” She turned to Dad, her voice now syrupy sweet. “Leo, had I known you were a man of such… status, I would have answered differently.”
Dad’s face darkened.
Before he could respond, I pointed across the room. “I know who you should be with, Dad.”
Dad followed my gaze and froze. His grip tightened. His expression shifted—confusion, shock… something deeper.
She turned. Her eyes widened, and she laughed—not cruelly, but warmly, like Mom used to.
“You’re the young man advertising your dad?” she teased. “All the ladies are waiting to be approached by you.”
Dad exhaled. “It’s… you.”
Years ago, Dad and Billie had been inseparable. But her father disapproved, thinking Dad was too simple, and they were torn apart. Now, Billie worked with at-risk kids—the same ones Dad’s company helped.
“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.
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.
Source: thecelebritist.com