Having regular customers is a normal part of the job for diner waitress Jess. But recently, a man has been leaving her a $100 tip every Sunday. After she posts a photo of him online to thank him for his kindness, Jess’s life changes instantly.
After two years at Denny’s, we had our usual regulars, just like any other local diner. You get used to them and even grow to enjoy them.
There’s the elderly couple who always split a stack of strawberry pancakes, the teenagers who come in after their Sunday soccer matches, the woman and her kid who order chicken and waffles every Wednesday, and the hipster guy who eats the same omelet every Thursday.
But one customer stood out from the rest.
He wasn’t loud or flashy. He probably never said more than ten words to me. Just his order and a quick “Have a good day” before he left. He came in every Sunday morning right when we opened.
He was an older man in a worn-out plaid shirt, his face lined with age, but his piercing eyes didn’t look at you—they looked through you.
He always sat in the booth by the window. The one that gave a clear view of the parking lot. He would stay through my whole shift, sipping coffee, ordering a slice of pie, maybe a club sandwich around midday, all while watching TV.
At the end of his visit, he’d hand me the bill, smile, and leave a $100 tip.
Every single time.
Honestly, those tips made my week. I don’t earn much, so that $100 went toward bills, groceries, or sometimes just helped me stay sane.
“I don’t get why he does it, Rose,” I told my coworker as we ate our free meal at the end of our shift.
“Maybe he’s just one of those lonely old guys,” she said, drenching her fries in ketchup. “Or maybe you remind him of someone he lost.”
“Don’t make it weird,” I laughed, sipping my chocolate milkshake.
He kept doing it, and I never truly understood why. There was nothing remarkable about him—just an older man who seemed to enjoy quiet places like our diner.
But after a few months, I started to wonder.
Was he just really generous? Maybe his life felt empty. Maybe he had no family or friends, and the diner helped him feel less alone. Maybe he saw something in me. Maybe Rose was right—maybe I reminded him of someone he once loved.
Who knows?
As much as it nagged at me, I never asked. It didn’t feel right.
But one Sunday morning, something changed. The man looked tired, worn out. He sighed like the weight of the world was on his shoulders.
I tried making small talk, but he wasn’t interested.
“Can I get you anything else, sir?” I asked him three times that day.
“No, thank you, Jess,” he said, reading my name off my nametag just to make sure he got it right.
He asked for the bill and left his usual tip. But that day, I snapped a photo of him as he walked out.
“He came to the diner to be close to you without hurting you. That picture? That’s him, Jess.”
Later that night, once I got home, I posted the picture online with a short caption saying how much this man’s kindness had meant to me over the past few months. I said how thankful I was for him and for kind people like him.
It felt harmless.
But ten minutes later, my phone buzzed. I was nearly asleep and the sound startled me awake.
It was my mom.
I almost didn’t answer. I usually ignored her nagging on weekends. Our relationship was rocky, and I was tired of her trying to control my life without ever sharing hers.
But something made me pick up.
“Why did you post that?” she asked, her voice trembling and panicked.
She caught me off guard.
“What do you mean?” I asked.
“That man in the photo, Jessica. Oh my God… That’s your father!”
My heart dropped like a snapped rope.
“What? No. That can’t be!” I tried to process it. My dad? The man who left us when I was a baby? The man who abandoned my mom and me like we didn’t matter?
No. That couldn’t be. After he left, Mom got rid of everything. All the photos. All the memories. He was a ghost to me.
“Jess, listen to me,” my mom said, her voice trembling. “He… your dad came back, Jess. A few months ago. He’s not well. I think he has cancer. He wanted to see you. I told him to stay away. I was scared he’d hurt you again. But… I told him you work at Denny’s.”
A lump formed in my throat. I didn’t know what to say. Of course this would happen. Of course she talked to him behind my back.
Typical.
“He’s been watching you, Jess,” she said, crying. “He came to the diner to be near you without hurting you. That man in the picture—yes, that’s your father.”
I hung up without saying a word.
Everything stopped. I stared at my phone while sitting in bed. That quiet, kind man who always left me a $100 tip?
My dad?
He had been watching me, tipping me, sitting there every week—right in front of me.
I started crying before I even realized I was crying.
I remembered all his visits. He always sat by the window, quietly observing me when I wasn’t looking.
Maybe he didn’t speak because he was afraid I’d recognize him. But how could I? He was a stranger to me.
That $100? It wasn’t just money. It felt like guilt. Like he was trying to make up for all the time he missed. Every birthday. Every holiday. Every moment he left me alone, too young to understand what a father really was.
But that didn’t help.
How could it?
“Jess, I didn’t think you’d want to see me. I’m dying. I don’t have time left to hurt people. I just wanted to watch from a distance.”
That whole week, I waited for him to come in again. I wasn’t sure if he would. My mom probably told him I knew the truth.
But that Sunday morning? He showed up.
I walked up to him before he could sit.
“Why didn’t you tell me?” I asked.
His eyes softened. He looked older. Frailer.
“Jess, I didn’t think you’d want to see me. I’m dying. I don’t have time to hurt anyone anymore. I just wanted to see you,” he said.
“You left me. And now you’re here to relieve your guilt? How am I supposed to feel about that?”
“How else could I be near you? I just wanted to see you.”
I wanted to scream. To tell him his money meant nothing. That it couldn’t fix the years he missed. But I said nothing. I just stood there, shaking.
“I’m sorry, Jess,” he whispered.
And his eyes showed that he meant it.
I didn’t know what to say.
“Jess!” Rose called out, waving menus as my teen soccer players came through the door.
“I’m coming,” I said.
I turned away from my father.
Later, there was no $100 tip on the table. Just a word written on a folded napkin:
Sorry.
What would you have done?