Leo thought his son, Cole, didn’t notice his loneliness. But Cole did. Determined to find his widowed dad a wife, he devised a simple test. Most women failed. But at a charity gala, fate stepped in…
A Son’s Mission
Dad thought I didn’t notice. But I did.
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 like it could give him the answers he needed.
He was lonely.
And since he wouldn’t do anything about it, I would.
Armed with my special ring—an old bottle cap 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. Being fourteen, most of them found it adorable.
“Will you marry my dad?” I’d ask, dropping to one knee with a grin.
Some 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 great 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.
“And what does your wonder-dad do?”
“He’s a driver!” I’d say proudly.
And just like that, their smiles faded.
They assumed he was a businessman, a lawyer, maybe a doctor. But when they found out he was a driver, their enthusiasm drained like a popped balloon. Some nodded politely and walked away. Others forced an awkward laugh before disappearing.
What they didn’t know was that Dad owned a transportation company. But he still drove because he loved it. He said it kept him grounded. So, yeah—technically, he was a driver.
But one woman, the worst of them all, sneered in my face. I had thought she was perfect with her bright red hair, like fire shining on her head. But I was wrong.
“A driver? Little boy, you think he’s good enough for me?” she scoffed, rolling her eyes at Dad’s picture. “Try again, kiddo. I’m sure someone out there wants to meet your father. I’m not one of them.”
Then she walked away, leaving me stunned.
That night, I sat across from Dad as he stirred his soup absentmindedly. His wedding band still rested on his finger. I tapped my spoon against the table.
“Dad?”
He looked up, blinking like I had pulled him from deep thought.
“Yeah, Cole? You okay?”
“Do you ever think about dating again?” I asked.
Dad stiffened for just a second before giving me a half-smile.
“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, 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.”
That made him pause. His jaw tensed like he was fighting something. Then he finally exhaled. “I know.”
But I wasn’t giving up yet.
Testing the Waters
The next time we went grocery shopping, I spotted a woman in the fresh produce aisle. She seemed perfect. Pretty, well-dressed, and she was buying watermelon—my favorite fruit.
I ran up, 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 the best care of me. He’s generous beyond anything, and—”
She laughed. “That sounds amazing! What does he do?”
“My dad is a driver.”
Her face froze. “Oh… Well, good luck with that!” she said quickly before vanishing.
The next woman was even worse. “Your dad sounds great, but I’m looking for someone with a little more… stability.”
I clenched my fists, finally understanding. This wasn’t about love. It was about status.
Fate Steps In
A few weeks later, Dad and I attended a charity event. His company helps provide free transportation for foster kids, sick veterans, and low-income workers. He had been invited as a guest speaker.
As he stood at the podium, I wandered the room. Then I saw her—the one.
She had a warm smile, a kind presence. But before I could approach, my stomach dropped.
Across the room, standing beside my dad, was her.
The redhead from the library.
She was flirting with him.
No. No way.
I stormed over and grabbed Dad’s sleeve. “Dad, stop. She’s not the one.”
She gasped. “Excuse me?”
“You don’t remember me from the library? I proposed.”
Dad looked confused. “Proposed? Cole, what on earth?”
“Really? You don’t remember me? You don’t remember my dad? The driver.”
Recognition flickered across her face. But instead of looking guilty, she scoffed.
“Oh, that? Please. Kid, you made it sound like he was some cab driver. Had I known who you really were, Leo…” She placed a hand on his arm, her voice suddenly sweet. “Had I known you were a man of such… status, I would have answered differently.”
Dad’s face darkened.
Before he could speak, I pointed. “I know who you should be with, Dad.”
He followed my gaze and froze.
There she was. The warm, kind woman.
His grip on my hand tightened. His expression shifted—confusion, shock, something deeper.
Then she turned, and her eyes landed on him.
And she laughed. Not like the redhead, but warmly—like Mom used to.
“Wait! 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.”
Turns out, they had history.
Her name was Billie. She had loved Dad once, but life pulled them apart. Now, fate had brought them back together.
I grinned. “Guess my job here is done.”
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.
