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Grandpa Joins a Dating App

When Swiping Right Turns into a Family Affair

By B Pily Published about a year ago 4 min read

It all started on a quiet Sunday afternoon when Grandpa Jo—short for Joseph but definitely not short for mischief—sat on the couch with his ancient reading glasses perched on his nose. I should’ve been suspicious when he asked me, “What’s a ‘dating app,’ and why do people swipe?”

Being the tech-savvy genius of the family, I gave him a quick and very sanitized explanation: “You swipe right if you like someone and left if you don’t.” Grandpa simply nodded, but I caught the twinkle in his eye—the same twinkle that usually meant trouble was brewing.

Two days later, chaos erupted in the Jones family household.

The Profile of a Legend

It was my sister Tina who discovered it first. She burst into the living room holding her phone like it was about to explode.

“Has anyone seen Grandpa’s Tinder profile?!” she yelled.

“What?” Mom dropped her ladle, narrowly missing the spaghetti pot.

“Oh, it’s bad. Really bad,” Tina said, shaking her head while laughing so hard she could barely breathe.

We gathered around her phone to witness the masterpiece Grandpa had created. There he was, front and center: wearing his WWII veteran cap, holding a giant trout, and flexing what could only be described as a bicep from the 1970s.

His bio read:

"Joseph, 82. Love long walks to the fridge, unbeatable at bingo, and looking for a spicy lady to share my Jell-O cups with. Swipe right if you’re tired of immature boys—I’m old but gold.”

Mom clutched her chest. “Oh dear Lord.”

But the pièce de résistance was his “About Me” section:

"Hobbies: Power naps, judging people’s cooking, and watching soap operas like they’re war documentaries. Dealbreakers: People who don’t salt their food and women who think bingo isn’t a sport.”

“I’m deleting this,” Mom announced, reaching for Tina’s phone.

“Too late,” Tina said, smirking. “He already has 32 matches.”

Grandpa’s First Match

Things escalated quickly. By dinner, Grandpa had matched with a woman named Dolores, a 78-year-old widow who described herself as a “retired roller-skating champion with a passion for knitting and rebellion.”

We tried to intervene, but Grandpa wasn’t having it.

“You kids have your fun. Why can’t I?” he said, casually buttering his toast. “Besides, Dolores sounds like a real firecracker. I haven’t been this excited since Nixon resigned!”

“Grandpa, Tinder isn’t a game!” I protested.

He raised an eyebrow. “If it’s not a game, then why is it so much fun?”

The Date to End All Dates

Fast-forward three days. Grandpa had convinced Dolores to meet him at the local diner, and naturally, we couldn’t let him go alone. Not because we didn’t trust him—but because we absolutely didn’t trust him.

Tina, Mom, and I sat two booths away, pretending to read menus while spying on what would go down in family history as the most surreal date of all time.

Grandpa arrived in his finest suit—a tweed ensemble from a time when disco balls were cutting-edge. Dolores was already seated, wearing a sequined blouse that could probably double as a disco ball.

“Dolores, you look like a million bucks, and I mean before inflation!” Grandpa exclaimed.

Dolores giggled. “And you look just like your profile picture—handsome and holding a fish.”

As their conversation flowed, we overheard gems like:

Dolores: “What’s your secret to staying young?”

Grandpa: “Three words: naps, bacon, and grudges.”

Disaster Strikes

The date was going surprisingly well—until Grandpa decided to impress Dolores by demonstrating his “youthful agility.” He attempted a backbend in the middle of the diner.

Spoiler alert: Grandpa cannot do a backbend.

The entire diner froze as he slowly tipped backward like a felled tree. Dolores screamed, “Joseph, no!” as Grandpa landed on the linoleum floor with a thud.

“Did it look cool?” he groaned.

Dolores bent down, laughing so hard she nearly joined him on the floor. “It looked like you were trying to audition for Cirque du Soleil, but forgot you’re 82.”

By the time we helped him up, the entire diner was clapping, and Grandpa had secured a second date.

The Family Intervenes

After the diner debacle, we decided it was time for an intervention. Grandpa, however, was not having it.

“You think you can control me just because I don’t know how to clear my search history?” he snapped.

“That’s literally part of the problem,” I replied.

But Grandpa was on a roll. “I fought in wars, built my own house, and survived four kids under five. If I want to date a roller-skating rebel, I will!”

The Roller Derby Incident

True to his word, Grandpa went on that second date with Dolores. She invited him to her weekly roller derby match—a sport Grandpa grossly underestimated.

He showed up in loafers, thinking he’d cheer politely from the sidelines. Dolores had other plans.

“Joseph, you’re joining my team!” she declared, shoving a helmet on his head.

The next hour was a blur of chaos. Grandpa, wobbly on skates, managed to score a goal but also accidentally knocked over half of Dolores’ team. At one point, he yelled, “This is harder than storming Normandy!”

By the end of the match, Grandpa had a bruised ego, a sprained wrist, and a newfound respect for Dolores’ hobbies.

The Proposal

Three weeks and countless dates later, Grandpa dropped the biggest bombshell yet. At family dinner, he stood up, cleared his throat, and said, “I have an announcement. Dolores and I are getting married.”

Cue collective choking on spaghetti.

“You’ve known her for three weeks!” Mom shrieked.

“And three weeks is all it took for me to realize she’s the love of my life,” Grandpa replied, unfazed. “Besides, when you’re 82, time isn’t exactly on your side.”

Happily Ever After (Kind Of)

The wedding was a small but hilariously chaotic affair. Grandpa wore his WWII cap, Dolores wore roller skates, and their vows included phrases like “till death—or bingo—do us part.”

As they danced awkwardly to Sinatra’s “Fly Me to the Moon,” Grandpa winked at us. “Told you kids Tinder isn’t just a game.”

Final Thoughts

Grandpa’s Tinder adventure taught us two things:

  1. Love can strike at any age.
  2. Never underestimate an 82-year-old with Wi-Fi.

And as for Dolores? She’s the perfect match for Grandpa—bold, funny, and just as unpredictable. Together, they remind us that life is too short not to swipe right on adventure.

ComedySpecialsComedyWritingFamilyFunnyHilariousLaughterComedicTiming

About the Creator

B Pily

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