I Skipped Medicine and Lived Under a Leaking Roof to Send My Grandson $200 Every Month – Then I Found Out He Owned a Vacation Home and I Taught Him a Lesson

For years, I sacrificed comfort and health to help the grandson I raised, believing he was barely getting by. But one birthday call with his son revealed an unexpected truth I never saw coming.

My name's Jackie, and I'm 80 years old. I've lived in the same house in a small town for over five decades, and the roof has leaked since I took on the role of guardian for my grandson. It remained that way because I wasn't living for myself; I'd made a promise to my late daughter.

I used to call my house "cozy," but now it's just cold and broken. Still, I stayed put, not as if I had a choice. For years, I told myself that all the little things I went without were worth it because I was living for my grandson, Dylan.

He was my late daughter Molly's only child. She died when she was only 35, and Lord, I don't think I've drawn a deep breath since the day we buried her.

I raised Dylan from the time he was 13 and still remember how tightly he clutched onto my coat at her funeral. How small he looked, even though he was already almost taller than me.

From that moment on, I made him a promise, not out loud or for show. But it was one I repeated every morning while standing at the kitchen sink: "I'll carry you as far as I can, Dylan. I'll carry you as long as I breathe."

And I did, even when it hurt and no matter the cost.

That boy became my reason to keep going.

So I worked hard.

I only had one major skill, sewing. So, I sewed and sold everything I could just so my grandson could have it better. My work included making shirts, socks, and turning old linens into baby bibs.

I also made blouses, which I hawked at flea markets and church sales along with the other items for a few dollars each.

So much time was spent on that old sewing machine that I became quite good at fixing buttons and darning holes. When my fingers grew stiff and ached from arthritis, I wrapped them and continued.

The truth was, I didn't have much, but I always made sure Dylan had what he needed.

By the time he started staying on his own, with roommates, he'd still call me, saying, "Grandma, can you send a little for rent this month?" or "Grandma, we're short on groceries. Just a hundred would help."

He always sounded so tired and worn down on the phone, like he carried the weight of the world on his shoulders. I imagined him with sunken eyes, trying to keep his young family afloat.

That picture in my head made it easier to open my wallet, even when I knew I couldn't afford to.

Even after he married Jenny, the calls continued. More, in fact.

When he said the student loans were suffocating them, I sent more. His requests multiplied when the baby, little Leo, came.

"The baby's teething," or "We had to buy a formula."

"Diapers are so expensive now," as if they were ever cheap.

He also still called me about rent, and every time he did, I always found a way.

I sold my wedding ring, then my mother's gold locket.

I told myself it didn't matter, that things are just things, and people are what count.

Month after month, I sent Dylan two, sometimes three hundred dollars, no matter how tight things got. I know it doesn't sound like much to some, but when you live off Social Security, it's a small fortune. More than once, I skipped my blood pressure medication because he needed "a little extra this month."

Then came the winter of my 79th year. My house was so cold that I wore two sweaters, long johns, and gloves to bed.

One morning, I woke up with a thin layer of frost on the inside of the window. I got pneumonia not long after and spent four days in the hospital!

But that's not all.

When I returned to my cold, drafty home, the ceiling above the kitchen table had collapsed. I didn't have the strength or money to fix it. I put a tarp over it and moved the table to the corner, while eyeing the peeling walls from damp winters.

But I never said a word to Dylan. I didn't want to make him feel guilty, and I told myself it didn't matter, as long as my family was safe and warm. I figured that if I didn't tell him, he wouldn't worry.

And then came my great-grandson's fourth birthday.

I couldn't travel anymore; my legs were too weak, and I got dizzy. So I called to sing him "Happy Birthday" instead.

"Happy birthday, sweetheart!" I said when I was done, trying to keep my voice bright.

"Grandma!" he squealed, his voice lighting up. "When are you coming to our house by the sea?"

I froze, thinking I must've misheard. My hearing's not great these days.

"Your what, honey?"

"Our house by the sea! It's so big, Grandma! Daddy says we live here now, not by the little house anymore. That's just for when 'some people' come. Like when you came last time! But we don't go there. Daddy says this one is better 'cause it has a pool and—oh! Daddy's here! Here, talk to him!"

I gripped the armrest of my chair. I was sitting in my frigid living room with cracked plaster on my cold kitchen wall while a teacup balanced on my lap.

The word "big" kept echoing in my mind.

My sewing machine sat in the corner, silent for once, as I pondered the new information about the house by the sea.

Then Dylan came on, smooth as always.

"Hey, Grandma. How are you feeling?"

I lied about how well I was doing and asked how work was going, how Jenny was, and what Leo was into these days. He told me all the right things, even laughed a little, like everything was normal.

I pressed my lips together, forcing down the heat burning in my throat. For years, I had scraped by, skipping medicine, rationing heat, and sometimes even food just to keep him afloat when he called, crying about poverty.

My back ached from patching leaks with buckets, my hands stiff from the cold of winters spent under a roof that groaned with every storm. All the while, Dylan was raising his family in a house by the ocean, with a pool, no less!

The realization hit like a slap: if they could afford such a place, why did he keep calling, swearing they were barely surviving?! Why did he keep begging me to send what little I had left?!

Still, I continued playing dumb. I asked about the "small place" I had visited last. Dylan kept the story going with perfect ease, never once faltering or giving anything away for me to latch onto.

Then, at the end, just before we hung up, and almost casually, as though it were nothing at all, he said, "Oh, and if you could send a bit extra this month, that'd be great. Leo's birthday party was a bit over budget."

That's when something in me cracked, not like glass, but like old wood under too much weight.

My voice was steady, firm, as if I had rehearsed every word.

"I'm not sending any more money, Dylan."

There was a pause, then that familiar whine crept in.

"Grandma, what are you talking about? We just need a little help this month, and—"

"No. I'm not sending another cent. You've got a beach house with a pool. And you've been lying to me."

Silence.

I pressed on.

"I've covered your last two loans. I have the bank receipts. If you don't pay me back, I'll file for elder financial abuse. And don't think I won't."

"Grandma—wait, I didn't mean—"

"You want to make it right?" I cut him off. "Come fix my roof. You bring Leo with you, 'cause I miss him. You do this, or I'll go to the police."

He didn't speak for almost a full minute.

"I'll be there next week," he said at last.

When Dylan pulled into my driveway with a rental truck and his wife in tow, he looked like he hadn't slept in days. I stood on the porch, arms crossed, wrapped in my quilted coat.

Jenny didn't meet my eyes. I wasn't sure if she knew what her husband had been doing. She left Leo behind and returned to the hotel down the road while Dylan and two of his buddies set up ladders and pulled out roofing supplies.

My grandson worked for five days straight.

I smiled as I watched him hammer, sweating and swearing under his breath. And every evening, I spent time with Leo. We made cookies, played cards, stitched together a tiny pillow for his toy dinosaur, and laughed until my sides hurt.

One evening, after a dinner of tomato soup and grilled cheese, Dylan sat quietly on the living room couch. He looked older than his 32 years, weighed down not by poverty but by shame.

"Why did you do it, Dylan?" I finally asked the question that had been weighing on me. "Why lie to me and treat me this way?"

He rubbed his forehead and sighed.

"I don't know. I guess... I got used to it. You always helped. And when things were good, I figured it didn't hurt to keep receiving the help. Even two hundred dollars is money, easy money. But maybe... maybe I should've been kinder. Maybe then you'd still trust me."

I looked him in the eye.

"Trust isn't something you can buy back. You broke it."

He nodded slowly, with no arguments this time.

The next morning, he left quietly. The roof didn't leak anymore. The new shingles looked out of place against the rest of the weathered house, but I didn't mind. They reminded me of a hard lesson, finally learned.

Now I see Leo more often. Dylan brings him by once a month, always with a new story and a fresh box of pastries from the bakery downtown. He never asks for money anymore, and I never offer.

Last week, for the first time in decades, I bought myself a new coat. It's bright red, warm, and not secondhand.

Because sometimes, the best revenge isn't shouting, suing, or even cutting someone off. It's standing tall, demanding respect, setting boundaries, and finally choosing to live for yourself.

When Dylan handed me a birthday card this year, he didn't put a check inside. Just a note written in his shaky handwriting. It said:

"Thanks for loving me when I didn't deserve it."

I folded it and slipped it in my drawer, right below the envelope and the little pillow Leo and I made together.

If this story resonated with you, here's another one: When a woman's stepsister demanded a custom cake from their grandmother, no one expected her to try to return it half-eaten for a refund.

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.