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A Boss Asked His Employee to Take His Daughter to Prom – But She Told Him, ‘My Dad Didn’t Choose You by Accident. And It Wasn’t for My Sake’

By Mr. Jacklin
November 2, 2026 3 Min Read
0

A Boss Asked His Employee to Take His Daughter to Prom – But She Told Him, ‘My Dad Didn’t Choose You by Accident. And It Wasn’t for My Sake’

I thought my boss was doing his daughter a favor when he asked me to help out. But one strange message on her phone made me realize I’d walked into something I knew nothing about.

“My dad didn’t choose you by accident. And it wasn’t for my sake.”

I stared at Georgia. “What does that mean?”

She glanced toward the prom venue, then back at me. “Brent, my dad’s been watching you for months.”

My stomach tightened.

“What does that mean?”

“Watching me do what?”

“How you handle problems. How you treat people. Whether you lose your temper.”

I frowned and immediately started sweating. “Wait, did I do something wrong? You’d tell me if I did something to make him upset, right?”

“No. That’s the problem.”

Before I could ask another question, her phone buzzed.

“Watching me do what?”

Georgia glanced at the screen and groaned. “It’s Dad.”

She showed me the message.

“Remember our agreement. Don’t make things too easy for him.”

“Georgia, what exactly did I agree to?”

She sighed. “Something my father thinks is brilliant.”

She showed me the message.

***

I’d started working for Sheldon when I was 19.

His company supplied restaurants and grocery stores with food packaging and cleaning products.

I needed that job more than he probably realized.

My mom, Denise, was raising my younger sister, Janelle, alone.

I needed that job.

Money was always tight, so I gave Mom part of every paycheck for groceries, utilities, and whatever Janelle needed for school.

I never showed up late.

I never called out unless I absolutely had to.

And if Sheldon asked me to stay an extra hour, I did.

Within a year, I’d become the employee he trusted with everything from deliveries to closing up at night.

I never showed up late.

Sheldon was a decent boss, but he had strange habits.

He loved asking questions.

“What would you do if a customer refused to pay an invoice?”

“What if two employees wanted the same day off?”

“What if a supplier delivered the wrong order?”

He loved asking questions.

I’d answer, and he’d nod like he was grading an exam.

I assumed he was simply obsessed with running the business well.

Then one Friday afternoon, he called me into his office.

***

“I need a favor, Brent.”

“Sure.”

He hesitated. “My daughter’s prom is tomorrow.”

He called me into his office.

Georgia was 18. I’d seen her around the office a few times, but we barely knew each other.

“The boy she was supposed to go with backed out,” Sheldon continued. “I want you to take her.”

I thought he was joking. “Me?”

“You’re responsible. I trust you.”

Then he added, “Do this for me, and I’ll make it worth your while.”

“I want you to take her.”

I thought about Mom’s broken washing machine and Janelle’s worn-out school shoes.

I knew that if my boss gave me extra money for being his daughter’s date, it would make things a little easier for my mom and sister.

“Okay.”

Sheldon looked relieved.

Almost too relieved.

Sheldon looked relieved.

 

Click here to continue reading PART 2: A Boss Asked His Employee to Take His Daughter to Prom – But She Told Him, ‘My Dad Didn’t Choose You by Accident. And It Wasn’t for My Sake’

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