Jess, a waitress at a diner, is used to having her regular customers. But lately, there’s been a new one: a man who leaves her a $100 tip every Sunday without fail. Things escalate when Jess posts a photo of the man online, thanking him for his generosity… only for her entire world to change in an instant.
I’ve worked at Denny’s for two years now, and, like any small diner, we’ve got our regulars. You get used to them, and they become a welcomed part of your day.
A smiling waitress | Source: Midjourney
I have the retired couple who always split a stack of strawberry pancakes, the group of teens who come in after their Sunday soccer games, the mom and toddler who eat chicken and waffles every Wednesday, and the hipster guy who orders the same omelet every Thursday.
But out of everyone, there was one customer who stood out the most.
He wasn’t flashy or loud. In fact, I don’t think he ever said more than ten words to me. It was just his order and, “Have a good day,” when he left. But every Sunday morning, right when we opened, he’d walk in.
An elderly couple sitting in a booth at a diner | Source: Midjourney
He was an older man, always wearing a worn-out plaid shirt, his face lined with age, but his eyes were sharp, like he was looking through you, not at you.
Without fail, he’d sit at the booth by the window. You know, the one that gives you a clear view of the parking lot. He’d stay the entire shift, sipping coffee, ordering a slice of pie, maybe a club sandwich around noon while he looked at the television above.
A man sitting in a diner | Source: Midjourney
And when it came time to leave, he’d hand me the bill, smile gently, and leave a $100 tip.
Every. Single. Time.
I can’t lie, those tips made my week. I’m not rolling in cash, and that extra $100 went toward bills, groceries, and, honestly, sometimes just keeping me sane.
A note on a table | Source: Midjourney
“I don’t understand why he does it, Rose,” I told my friend when we sat down to eat our complimentary meal at the end of the shift.
“Maybe he’s one of those lonely men, Jess,” she said, drowning her fries in ketchup. “Or you remind him of a relative or something.”
“Don’t make it weird,” I laughed, sipping on my chocolate milkshake.
A waitress drinking a chocolate milkshake | Source: Midjourney
But I also never quite understood why he did it. He didn’t seem rich; he was just your average older guy who preferred quiet places like our diner.
After a few months of it happening, I started to wonder: Why?
I mean, was he just insanely generous? Maybe he didn’t have anyone in his life anymore. No family, no close friends… Maybe the diner was his escape from loneliness. I even thought, maybe he saw something in me. And maybe Rose was right; maybe he thought I reminded him of someone he lost.
A close up of a woman | Source: Midjourney
Who knows?
Still, as much as it bugged me, I didn’t ask. It didn’t feel right.
One Sunday morning, though, something hit different. He looked more tired than usual, and he sighed a lot. It was like he had the weight of the world on his shoulders.
I tried to make some small talk, but he wasn’t really having it.
A waitress holding a notebook | Source: Midjourney
“Sir, can I get you anything else?” I asked for the third time that day.
“No, thank you, Jess,” he said, his eyes checking out my nametag to make sure he got my name right.
Eventually, he asked for the bill and left his usual tip. But as he was leaving, I snapped a quick photo of him.
“He’s been coming to the diner because he wanted to be close to you without causing any more damage. That’s him in the picture, Jess.”
A waitress holding her phone | Source: Midjourney
When I got home later that night, I sat in my bed and decided to post the photo online, with a caption about how this man’s generosity had simply brightened my Sundays for months. And how grateful I was for people like him in the world.
It was innocent enough.
Less than ten minutes after I posted it, my phone buzzed. I was already falling asleep, so it shook me awake with a start.
A woman sitting in bed | Source: Midjourney
It was my mom.
I almost didn’t answer. Weekends were the only time I didn’t allow her constant nagging to irritate me. We had a shaky relationship, and I was tired of her trying to micromanage me while not telling me anything about her own life.
But something in my gut told me to pick up.
A woman looking concerned | Source: Midjourney
“Why did you post that?” she asked, her voice shaky, almost panicked.
For once, she caught me off guard.
“What do you mean?” I asked.
“The man in the picture! Oh my goodness, Jessica. That’s your father!”
A shocked older woman talking on the phone | Source: Midjourney
I felt my heart drop like someone had cut the cord holding it in place.
“What? No. It can’t be!” I said, trying to piece it together. My dad? My dad? The same man who left us when I was a baby? The man who walked out on my mom and me like we didn’t matter at all?
No. There was no way. He was long gone, and when he left, my mother had thrown out everything, including photos of him. To me, the man was a ghost.
A shocked woman sitting in bed | Source: Midjourney
“Jess, listen to me,” my mom’s voice was trembling now, and I could hear her pacing through the phone. “He… Dad came back, Jess. A few months ago. He’s been sick. I think it’s cancer. And he asked to see you. I told him to stay away. I didn’t want him to hurt you again. But I did mention that you worked at Denny’s.”
My throat tightened. I didn’t know what to say. Of course, this would happen. Of course, she would be in contact with him and not mention anything to me.
Typical.
An upset woman | Source: Midjourney
“He’s been watching you, Jess,” she continued, barely holding back tears. “He’s been coming to the diner because he wanted to be close to you without causing any more damage. That’s him in the picture, Jess. That’s your dad.”
I hung up without saying anything.
It felt like the world had stopped. I sat in my bed, staring at my phone. This man, this kind, quiet man who had tipped me $100 each time without fail…
A man sitting in a diner | Source: Midjourney
My father?
He’d been sitting in front of me for months, watching, tipping, just waiting.
Tears started spilling down my cheeks before I even realized what was happening.
I thought back to his visits at Denny’s. The way he’d just sit there, sometimes watching me when he thought I wasn’t looking, how he always asked for the booth by the window.
A man sitting in a diner booth | Source: Midjourney
The way he never said much… maybe because he was scared that I’d recognize him. But how could I? I didn’t even know the man.
That $100 tip? It wasn’t just money. It was guilt. It was his way of making up for the years he’d missed with me. All the birthdays, the Christmases, for walking out when I was too young to even understand what a father was supposed to be.
A frowning young woman | Source: Midjourney
But that didn’t fix anything.
How could it?
“I didn’t think you’d want to see me, Jess. And I’m dying. I don’t have time to hurt the people around me. I wanted to watch from afar.”
I spent the week waiting for him to come back to the diner. I wasn’t sure he would show up. My mother probably told him that I knew the truth.
A waitress looking pensive | Source: Midjourney
But on Sunday morning? There he was, like always.
I didn’t even give him time to sit down before I walked up to him.
“Why didn’t you tell me?” I asked.
His eyes softened. He looked older than I remembered, more fragile than I’d noticed before.
A man sitting in a booth at a diner | Source: Midjourney
“I didn’t think you’d want to see me, Jess. And I’m dying. I don’t have time to hurt the people around me. I wanted to watch from afar,” he said.
“You’re my father, and you left me. And now you show up here, what, to tip me out of your guilt? How do you think that’s supposed to make me feel?”
“I didn’t know how else to be near you. I just wanted to see you.”
An upset man sitting in a booth in a diner | Source: Midjourney
I wanted to scream, to yell, to tell him that his money didn’t mean anything. That he couldn’t replace the years he’d abandoned me. But instead, I stood there, trembling.
“I’m sorry, Jess,” he whispered.
There was real regret in his eyes.
But I didn’t know what to say.
“Hey, Jess!” Rose called me, holding menus and nodding toward my group of teenage footballers who had just walked in.
A smiling waitress holding menus | Source: Midjourney
“Coming,” I said.
I turned away from my father.
Later, there was no $100 tip on the table. Just a folded-up napkin with one word:
Sorry.
What would you have done?
A note on a table | Source: Midjourney
If you enjoyed this story, here’s another one for you |
My Cousin Intentionally Sewed My Wedding Dress 2 Sizes Smaller – She Was Shocked When She Saw What I Did with It
When Jess and Michael get engaged, her cousin Sarah decided to sew her wedding dress for her as a gift. But during the final fitting, Jess discovers that the wedding dress is two sizes too small. Will Sarah fix her error, or will Jess have to take things into her own hands?
My cousin Sarah and I have always had a complicated relationship. She’s loud and bubbly, but also the type of person who craves the spotlight. And because of that, our entire family gave her the attention she wanted. It made more sense to shine the spotlight on Sarah, rather than ourselves.
When Michael and I got engaged after being together for four years, my whole family seemed genuinely excited for me.
A couple standing together | Source: Midjourney
Sarah even got all of our girl cousins together, along with my best friends, for a night out. Ending in an Airbnb where we continued the party, because I was the first of us to get engaged.
During that night out, Sarah came up to me, a glass of champagne in her hand.
“Jess! I have a great idea!” she said.
A smiling woman holding a glass of champagne | Source: Midjourney
“What?” I asked. “What do you want to do?”
“I want to make your wedding dress for you!” she exclaimed, swaying to the music as she spoke.
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.
The author and publisher make no claims to the accuracy of events or the portrayal of characters and are not liable for any misinterpretation. This story is provided “as is,” and any opinions expressed are those of the characters and do not reflect the views of the author or publisher.
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