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Customer Tipped Me $100 Every Sunday—When I Found Out Who He Was, I Cried

By World WideMay 15, 2025No Comments8 Mins Read
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Having regular customers is normal for diner waitress Jess. Recently, a man leaves her $100 every Sunday. After posting a photo of the man online to thank him for his generosity, Jess’s life changes instantly.

After two years at Denny’s, we had regulars like any local diner. You adjust to them and enjoy them.

 

I have the elderly couple who always split a stack of strawberry pancakes, the adolescents who come in after Sunday soccer games, the woman and kid who eat chicken and waffles every Wednesday, and the hipster guy who eats the same omelet every Thursday.

However, one customer stuck out.

He wasn’t garish. He probably never spoke more than ten words to me. Just his order and “Have a good day,” before leaving. He came in every Sunday morning when we opened.

 

He was an old man in a worn-out plaid shirt with a lined face, yet his piercing eyes looked through you, not at you.

He always sat at the window booth. The one that shows the parking lot clearly. He would stay all shift, sipping coffee, ordering pie, and possibly a club sandwich at midday while watching the TV.

 

He gave me the bill, smiled, and left a $100 tip when we left.

All the time.

I swear, those tips made my week. I don’t make much money, so the $100 went toward bills, groceries, and sometimes just staying sane.

 

“I don’t understand why he does it, Rose,” I told my companion as we ate our free supper at shift’s conclusion.

“Maybe he’s one of those lonely men, Jess,” she added, ketchup-drenching her fries. “Or you evoke a relative or something.”

“Don’t make it weird,” I laughed, drinking my chocolate milkshake.

 

He did it for reasons I never understood. He was nothing special—just an older man who liked peaceful places like our diner.

After a few months, I wondered why.

Was he outrageously generous? His life may have been empty. No family or close friends… Maybe the diner helped him avoid loneliness. It was possible he saw something in me. Maybe Rose was right—maybe I reminded him of someone he lost.

 

Who knows?

Though it bothered me, I didn’t inquire. It felt wrong.

However, something changed one Sunday morning. The man looked exhausted and sighed heavily. He felt like he carried the globe.

I tried small chat, but he wasn’t interested.

 

Can I get you anything else, Sir? I inquired three times that day.

“No, thank you, Jess,” he said, checking my nametag to be sure he got it right.

He requested the bill and tipped as usual. However, I took a brief photo of him leaving.

“He came to the diner to be close to you without hurting you. The picture is him, Jess.”

 

 

After getting home that night, I posted the photo online with a statement about how this man’s kindness has brightened my Sundays for months. I appreciated him and others like him.

It seemed harmless.

After posting, my phone buzzed within 10 minutes. Since I was falling asleep, it jolted me awake.

 

 

 

My mother.

I almost didn’t reply. Only on weekends did I ignore her relentless pestering. We had a rocky relationship, and I was weary of her micromanaging me and not informing me about her life.

My instinct prompted me to pick up.

 

 

 

“Why did you post that?” she asked, shaking and panicking.

For once, she surprised me.

“You mean what?” I requested.

Man in photo! Jessica, my goodness. Your father!

 

 

 

My heart sank like a rope was cut.

“What? No. Can’t be!” I tried to figure things out. My dad? My dad? The same man who left us as a baby? The guy who left my mom and me like we didn’t matter?

No. That was impossible. After he left, my mother threw out everything, even his photos. The man was a ghost to me.

 

 

 

“Jess, listen to me,” my mom trembled, pacing through the phone. “He… Dad returned, Jess. A couple months ago. He’s unwell. I suspect cancer. He wanted to see you. Stay away, I said. I feared he would hurt you again. But I said you worked at Denny’s.”

A knot formed in my throat. Not knowing what to say. Naturally, this would happen. Of course, she’d talk to him without telling me.

Typical.

 

 

 

“He’s been watching you, Jess,” she said, crying. “He came to the diner to be close to you without hurting you. Pictured is him, Jess. Yes, your dad.”

Without saying anything, I hung up.

The world seemed to stop. I stared at my phone in bed. This polite, quiet man consistently tipped me $100.

 

 

 

My dad?

He watched, tipped, and waited in front of me for months.

I started crying before I recognized it.

I remembered his Denny’s visits. He always requested the booth by the window and sat there, occasionally watching me while I wasn’t looking.

 

 

 

The lack of communication may have been due to fear of being recognized. How could I? He was unknown to me.

That $100 tip? It went beyond money. I was guilty. He made up for the years he missed me. All the birthdays and Christmases, for leaving while I was too young to grasp fatherhood.

 

 

 

That didn’t help.

How could?

Jess, I didn’t think you’d want to see me. I’m dying. I don’t have time to damage others. I wanted a distance view.”
The week I waited for him in the diner. Whether he would show up was uncertain. Mum probably told him I knew the truth.

 

 

 

But Sunday morning? He was always there.

I approached him without letting him sit down.

“Why didn’t you tell me?” I requested.

Eyes softened. He appeared older and weaker than I remembered.

 

 

 

Jess, I didn’t think you’d want to see me. I’m dying. I don’t have time to damage others. He stated he wanted to watch from afar.

My father, you left me. What, you’re here to relieve my guilt? How should that make me feel?

How else could I be near you? I wanted to see you.”

 

 

 

I wanted to scream and yell that his money meant nothing. It was impossible to replace the years he left me. Instead, I stood trembling.

“I’m sorry, Jess,” he muttered.

His eyes showed regret.

Not knowing what to say.

“Hi, Jess!” Rose called me, holding menus and gesturing to my adolescent footballers who had just entered.

 

 

 

“Coming,” I said.

Turning from my father.

The table had no $100 tip later. One word on a folded napkin:

Sorry.

What would you’ve done?

 

 

 

If you liked this tale, try another.

My Cousin Intentionally Sewed My Wedding Dress 2 Sizes Smaller—She Was Shocked by My Results.
After Jess and Michael were engaged, her cousin Sarah sewed her wedding dress as a gift. Jess discovers the wedding dress is two sizes too small during the last fitting. Will Sarah correct her mistake or must Jess act?

I’ve always had a complex relationship with cousin Sarah. She’s noisy and exuberant and seeks attention. Because of it, our family gave her the attention she wanted. It made more sense to highlight Sarah than ourselves.

After four years together, my family was ecstatic when Michael and I became engaged.

 

 

 

Sarah organized a night out with my best friends and all our lady cousins. Since I got engaged first, we continued the party in an Airbnb.

Sarah approached me with champagne that night out.

“Jess! She said she had a wonderful idea.

 

 

 

“What?” I requested. You want to do what?

“I want to make your wedding dress for you!” she said, swaying to the music.

Inspired by true events and people, this work is fictionalized for creativity. To preserve privacy and enrich the story, names, characters, and facts were changed. Any resemblance to real people, events, or places is unintentional.

The author and publisher neither guarantee event authenticity nor character characterization and are not liable for misinterpretation. While this work is presented “as is,” the characters’ viewpoints do not reflect those of the author or publisher.

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