Dating can be a minefield of awkward moments, unexpected mishaps, and unforgettable blunders. But sometimes, the worst dates make for the best laughs!
We’ve all been there — navigating the tricky waters of romance, only to end up with a story that’s more “oops” than “aww.” From blind date mishaps to creative loyalty tests, dating disasters are universal. But why cry over spilled wine at dinner when you can laugh about it instead?
We’ve rounded up nine hilarious jokes inspired by dating misadventures. Whether you’re single, taken, or somewhere in between, these punchlines will make your heart skip a beat — this time, from laughter!
A laughing woman | Source: Pexels
The Sunday School Surprise
I was swiping through a dating app and matched with someone who didn’t have a profile picture. Desperate for a change, I decided to take a chance and meet her.
I wasn’t expecting much, maybe someone a little rough around the edges, but when I arrived, I was floored. She was stunning: 5’2″, baby blue eyes, strawberry blonde hair, and all the right curves.
A young blonde woman | Source: Pexels
Impressed, I asked what she did for a living. “I teach Sunday school,” she said.
I’d never dated a Christian girl before, but I was intrigued. On the drive to dinner, I lit a cigarette and asked if she cared for one.
“Oh, heavens no,” she replied, “What would I tell my Sunday school children?”
A couple in a cafe | Source: Pexels
Fair enough, I thought. Some people smoke, some don’t.
At the restaurant, I ordered steak, she got lobster, and I requested the second-most expensive bottle of wine on the menu. When the wine arrived, she declined a glass.
“You don’t drink?” I asked, surprised.
A couple drinking coffee | Source: Pexels
She shook her head. “Oh, heavens no, what would I tell my Sunday school children?”
The dinner and conversation were amazing, but I couldn’t quite figure her out. On the drive home, I passed a cheap motel and figured, why not take a chance?
“Want to get a room and fool around?” I asked nervously.
A motel sign | Source: Pexels
She winked and said, “I thought you’d never ask!”
Surprised, I laughed and teased, “Really? What are you going to tell your Sunday school children about this?”
She grinned mischievously and said, “The same thing I tell them every week: You don’t have to smoke or drink to have a good time!”
A smiling blonde woman | Source: Freepik
The Widow’s Wardrobe Wisdom
Dorothy and Edna, two elderly widows, are talking.
Dorothy says, “That nice George Johnson asked me out for a date. I know you went out with him last week, and I wanted to talk with you about him before I give him my answer.”
Two elderly friends talking | Source: Pexels
Edna replies, “Well, I’ll warn you about what happened last week! George showed up at my apartment punctually at 7 P.M., dressed like such a gentleman in a fine suit, and he brought me such beautiful flowers!
Then he took me downstairs, and what was there but a luxury car… a limousine, uniformed chauffeur and all.
An elegant man | Source: Freepik
“Then he took me out for dinner… a marvelous dinner. Lobster, champagne, dessert, and after-dinner drinks. Then we went to see a show. Let me tell you, Dorothy, I enjoyed it so much I could have just died from pleasure! BUT THEN when we were coming back to my apartment, he turns into an ANIMAL!”
Dorothy exclaims, “Goodness gracious! What do you mean?”
A shocked elderly woman | Source: Pexels
“He tore my expensive dress off!”
“So, I shouldn’t go on a date with him?” Dorothy asks.
“No, I’m just saying… wear an old dress.”
A smiling elderly woman | Source: Pexels
Thomas’ Mom and Dad Dilemma
Thomas, 32, is still single. His friend asks, “Why haven’t you found a wife? Haven’t you met anyone you like?”
Thomas replies, “Oh, I’ve met plenty of wonderful women. But when I introduce them to my mom, she always disapproves.”
Two male friends talking | Source: Pexels
The friend suggests, “Easy fix—find someone just like your mom!”
Months later, they meet again. The friend asks, “So, did you try my advice?”
Thomas sighs, “I found a woman just like my mom. She’s perfect, and my mom adores her.”
“So, what’s the problem?”
A happy couple | Source: Pexels
“My dad can’t stand her.”
Blind Date Backup Plan
I went on a blind date with someone I met on a dating app. Neither of us had profile pictures, but I consider myself quite handsome. Still, I was nervous. What if she wasn’t my type?
A nervous man | Source: Pexels
Thankfully, I found an app called “Mom, Are You OK?” It schedules your phone to ring right after meeting your date. If you like them, you ignore the call. If not, you answer, “Mom? What’s wrong?” and quickly exit.
When I knocked on her door, my worries disappeared. She was absolutely stunning. But before I could say a word, her phone rang.
A happy woman talking on her phone | Source: Pexels
“Mom? What’s wrong? Are you okay?”
The Perfect Catch
A man is dining alone in a fancy restaurant when he notices a stunning redhead at the next table. Though he’s too shy to say hello, he can’t stop glancing her way.
Suddenly, she sneezes, and much to his surprise, a glass eye flies out of its socket, hurtling straight at him. He catches it mid-air with lightning reflexes and hands it back to her.
A man holding a glass eyeball | Source: Midjourney
Embarrassed, she says, “I’m so sorry! Please, let me buy your dinner to make it up to you.”
He joins her, and they have dinner, watch a show, order drinks, and have a deep conversation. At the end of the night, she invites him over, and he stays.
The next morning, she whips up a gourmet breakfast. Amazed, he says, “You’re absolutely perfect. Are you this kind to every guy you meet?”
A smiling man in bed | Source: Pexels
She smiles and replies, “Nope. You just happened to catch my eye.”
The Gym’s Secret Attraction Machine
After a tough breakup, I decided to turn my life around. Step one: Hit the gym to get back in shape and maybe catch the attention of someone special.
At the gym, I asked the trainer, “Which machine here will help me attract the most beautiful women?”
A man talking to a coach in a gym | Source: Pexels
He sized me up, paused, and said, “The ATM outside.”
A Mixed-Up Christmas Surprise
A man decides to buy his new girlfriend a Christmas present. Since they’ve only been dating for three weeks, he wants something thoughtful but not overly personal. He settles on a pair of elegant gloves.
A shopping mall during Christmas | Source: Pexels
To ensure he picks the right style, he asks her younger sister to come along and offer her opinion. The sister points out a chic pair of white gloves at the store, which he purchases. While shopping, the sister also buys herself a pair of panties.
Unbeknownst to them, the cashier accidentally swaps the packages. The man unknowingly ends up with the panties in the gift box instead of the gloves.
Two gift boxes | Source: Pexels
Feeling proud of his choice, he pens a heartfelt note to include with the gift:
My Dearest,
I chose these because I noticed you don’t usually wear any when we go out in the evenings.
If it weren’t for your sister, I’d have picked the longer style with buttons, but she said the shorter ones are easier to take off.
A man writing a note | Source: Pexels
They’re a delicate shade, but the saleswoman assured me they won’t show wear even after being used for three weeks. She even tried them on for me, and they looked fantastic!
I wish I could be there to help you put them on the first time. I’m sure others will handle them before I get the chance to see you again, but that’s okay.
When you take them off, don’t forget to blow inside to keep them fresh. They may feel a little damp after wearing, which is perfectly natural.
A white glove | Source: Freepik
Just think about how many times I’ll kiss them throughout the year. I hope you’ll wear them on Christmas Eve for me.
P.S. The latest trend is to fold them down slightly to let a bit of fur show.
A woman wearing white leather gloves | Source: Midjourney
The $5,000 Test
A man is dating three women and struggling to decide which one he should marry. To make his choice easier, he comes up with a test.
He gives each woman $5,000 and observes what they do with the money.
An envelope with money | Source: Pexels
The first woman spends all the money on herself. She visits an upscale salon for a makeover, buys a new wardrobe, and splurges on accessories. She tells him, “I wanted to look my best for you because I love you.”
The man is impressed.
A woman in a SPA | Source: Pexels
The second woman uses the money to buy him gifts. She gets him a premium set of golf clubs, upgrades his computer, and buys him tailored suits. Handing him the presents, she says, “I spent it all on you because I want to make you happy—I love you.”
Again, the man is impressed.
A shocked man | Source: Pexels
The third woman invests the money in the stock market. After making a significant profit, she returns his $5,000 and places the rest into a joint account. She explains, “I wanted to grow our future together because I love you.”
The man is blown away by her financial savvy.
He thinks long and hard about the women and their choices.
A man deep in thought | Source: Pexels
Finally, he marries the one with the biggest breasts.
Love and Semantics
An elderly couple, both widowed, had been dating for quite some time. After much encouragement from their friends, they finally decided to tie the knot.
One evening, before the wedding, they sat down for dinner to discuss finances, living arrangements, and so forth.
An elderly couple talking | Source: Pexels
Eventually, the gentleman cleared his throat and cautiously broached a sensitive topic: their physical relationship.
“How do you feel about making love?” he asked hesitantly.
The lady thought for a moment, then replied with a gentle smile, “I would like it infrequently.”
A woman with a soft smile | Source: Pexels
The man sat in thoughtful silence, adjusted his glasses, leaned closer, and softly asked, “Is that one word or two?”
Liked these jokes? Here are some more!
Marriage Counseling with a Twist
After 30 years of marriage, a husband and wife sit in front of a therapist. The wife starts in on a long list of grievances: “He doesn’t listen to me, he’s distant, we haven’t been close in ages. I feel neglected, lonely, unloved…”
A couple in therapy | Source: Pexels
She keeps going and going, pouring out years of frustration. Finally, the therapist stands up, walks around his desk, and approaches the wife.
He asks her to stand and proceeds to lean in and give her a long, passionate kiss. The husband looks on in surprise, and the wife? She’s left completely speechless by the intensity of their therapist’s kiss.
A shocked woman | Source: Pexels
The therapist turns to the husband and says, “Your wife needs this at least three times a week if you’re serious about saving your marriage. Can you manage that?”
The husband sits there, thinking for a moment before responding, “Well, sure. I can bring her by on Mondays, Wednesdays, and Fridays.”
A couple in therapy | Source: Pexels
Rich Man Humiliates Boy Shining Shoes in Underpass
“My dog could do a better job with his tongue!” A wealthy man insults a poor boy shining shoes in an underpass and refuses to pay. But fate brings them face-to-face again the very next day, with a surprising twist neither could have expected.
The underground passage echoed with the shuffle of hurried footsteps. Amidst the hustle, 14-year-old Martin sat quietly by the wall, his shoe-shining kit spread before him. His eyes darted hopefully at each passing shoe, praying for a customer…
A teenage boy sitting in an underpass | Source: Midjourney
“Just a handful,” he whispered to himself. “Just a handful today, please.”
As the day wore on, Martin’s stomach growled in protest. The meager breakfast of two bread slices felt like a distant memory. He reached for his water bottle, taking a small sip to quell the hunger pangs.
“You can do this, Martin,” he told himself. “For Mom and Josephine.”
The thought of his paralyzed mother and little sister waiting at home bolstered his courage. He plastered on his best smile, ready to tackle whatever the day would bring.
A sad boy in an underpass | Source: Midjourney
“Shoe shine, sir? Ma’am?” he called out, his voice barely audible above the din of the underpass.
Hours ticked by, but no one stopped. Martin’s hopes began to dwindle, but he refused to give up. As the afternoon sun beat down, he finally allowed himself a moment of respite. Digging into his worn leather bag, he pulled out a small orange, his lunch for the day.
Just as he began to peel it, a pair of dirty brown leather shoes landed in front of him with a heavy thud.
“Hurry up, kid. Clean it. I’m in a rush,” a gruff voice barked.
A brown leather shoe | Source: Pexels
Martin looked up, his heart racing with excitement and trepidation. The man towering above him exuded wealth from head to toe. This could be his chance for a good tip.
“Right away, sir!” Martin said, setting aside his orange and reaching for his supplies.
As he worked on the brown leather shoes, the man’s impatience grew. “What’s taking so long? I don’t have all day!”
A person brushing a brown shoe | Source: Pexels
Martin’s hands trembled slightly, but he focused on giving his best service. “Almost done, sir. I promise it’ll look great.”
The man scoffed. “At your age, I was already making more than my father. I wasn’t shining shoes like some beggar.”
Those words stung poor Martin. It had been three years since a drunk driver had taken his father’s life, leaving their family shattered. The memory of that fateful night still haunted Martin—the screeching tires, the sickening crunch of metal, and the devastating news that followed.
A grave in a cemetery | Source: Pexels
Just months after losing his father, Martin’s world crumbled further when his mother Mariam suffered a stroke, leaving her paralyzed. At just eleven years old, he had shouldered the burden of a provider, sacrificing his childhood to follow in his late father’s footsteps as a shoe shiner.
The memories threatened to overwhelm him, but he pushed them aside. He had a job to finish. He had a family to feed.
“You call this shining?” the man sneered, examining his shoe. “My dog could do a better job with his tongue!”
A wealthy senior man | Source: Freepik
Martin’s cheeks burned with shame. “I’m sorry, sir. I can try again—”
“Forget it,” the man cut him off, pulling out his phone. “Yeah, Sylvester here. Reschedule the meeting to 4. I’ll be late, thanks to this incompetent brat.”
As Sylvester ranted into his phone, Martin’s mind drifted to happier times. He remembered his father’s gentle hands guiding him, teaching him the art of shoe shining.
A distressed teenage boy | Source: Midjourney
“It’s not just about the shine, son,” he’d say. “It’s about dignity. Treat every shoe like it’s the most important one you’ll ever touch.”
“Hey! Are you even listening?” Sylvester’s sharp voice yanked Martin back to reality. “What’s your father doing, sending you out here like this? Too lazy to work himself, huh?”
Martin’s throat tightened. “My father… he passed away, sir.”
Close-up of a sad teenage boy | Source: Midjourney
Sylvester’s eyes narrowed. “Oh, I see. So your mother’s probably moved on with someone else, popping out more kids to send begging, right? Don’t you people have anything better to do?”
Martin’s fists clenched at his sides, but he forced a polite smile. “That’s $7, sir.”
“SEVEN DOLLARS?” Sylvester exploded. “For this pathetic excuse of a shine? I don’t think so, kid.”
Before Martin could react, Sylvester grabbed his shoes and stormed off, leaving Martin empty-handed and heartbroken.
A frustrated senior man | Source: Freepik
“Wait!” he called out, chasing after the man. “Please, sir! I need that money. Please!”
But Sylvester was already in his car, speeding away, leaving poor Martin stranded in a cloud of dust and disappointment.
He slumped against the wall, tears streaming down his face. He looked up at the sky, imagining his father’s face.
“I’m trying, Dad,” he whispered. “I’m really trying.”
His father’s last words echoed in his mind: “Remember, son. Never give up. Each bump is a step closer to your dreams. Remember.”
A sad boy looking up | Source: Midjourney
Wiping his tears, Martin returned to his spot. There was no time for self-pity. No time for tears.
The next morning, Martin was back at his usual spot, setting up his kit with determination. Suddenly, a commotion nearby caught his attention.
“Help! Someone help!” a woman’s frantic voice pierced the air.
Martin rushed towards the sound, his heart pounding.
A startled senior woman covering her mouth | Source: Freepik
A small crowd had gathered around a fancy car, and to his shock, he recognized the man inside. SYLVESTER. The same entitled man who had insulted him.
“He’s choking on an apple!” someone yelled. “The car doors are locked!”
Without hesitation, Martin grabbed a rock from the roadside and smashed the car window. Glass shattered everywhere as he reached in to unlock the door.
“Stand back!” he shouted, pulling Sylvester out onto the pavement.
A car with a broken window | Source: Pixabay
With all his might, Martin delivered several sharp blows to Sylvester’s back. Suddenly, a chunk of apple flew from Sylvester’s mouth, and he gasped for air.
“You… you saved me,” Sylvester wheezed, looking up at Martin with wide, shocked eyes.
Martin helped him to his feet, his own hands shaking. “Are you okay, sir?”
Sylvester nodded, still catching his breath. “I can’t believe it. After how I treated you yesterday… Why did you help me?”
Martin shrugged. “It was the right thing to do.”
A thoughtful senior man holding his glasses | Source: Pexels
Sylvester’s eyes filled with tears. “I’m so sorry, kid. I was horrible to you. Please, let me make it up to you. Name your price. Anything!”
Martin thought for a moment, then looked up. “Just the $7 from yesterday. That’s all I want.”
Sylvester stared at him in disbelief. “But… I could give you so much more. A new start, maybe?”
Martin shook his head. “I don’t need a new start, sir. I just need to take care of my family.”
Side view of a teenage boy | Source: Midjourney
Reluctantly, Sylvester handed over the money. As the crowd dispersed, he lingered, studying Martin’s face. “You’re quite something, kid. What’s your name?”
“Martin, sir.”
Sylvester nodded slowly. “Martin. I won’t forget this… or you.”
As Sylvester walked away to his car, Martin clutched the hard-earned money in his fist. He looked up at the sky again, a small smile beaming on his face.
“I remember, Dad,” he whispered. “I always do.”
A smiling teenage boy looking up | Source: Midjourney
The next morning, Martin was jolted awake by his sister’s excited screams.
“Marty! Marty! Come quick!”
He rushed outside, his mother calling after them in confusion. There, on their doorstep, sat a white bag bulging with cash and a note.
A bag full of cash | Source: Pexels
With trembling hands, Martin read aloud:
“Thanks is a small word for what you did. I know you’d refuse this. But you deserve a happy childhood. Took me just an hour to find your address. The world’s a small place, isn’t it?! Hope we meet again someday, and I hope you’re just the pure heart of gold you are!
— Sylvester.”
Tears of joy and shock filled Martin’s eyes. His sister jumped up and down, and their mother called out from inside, clearly shocked at seeing so much money.
“Martin? What’s going on?” she approached in her wheelchair.
A woman in a wheelchair | Source: Pexels
Martin’s mind raced. This money could change everything: his mother’s treatment, Josephine’s education, and their entire future. But was it right to accept it?
He walked to the small altar in their cottage, grabbing two pieces of paper. On one, he wrote “REMEMBER,” and on the other, “FORGET.” He folded them, shuffling them with his hands.
Lighting a candle before the crucifix, Martin closed his eyes. “Dad,” he whispered, “help me make the right choice.”
A burning wax candle against the backdrop of a cross | Source: Pexels
With a deep breath, he picked up a piece of folded paper and slowly opened it. A small smile lit up his face when he saw the word “REMEMBER.”
In that moment, Martin knew. He would accept the money, not for himself, but for his family. He would remember his father’s lessons, his own struggles, and the kindness that can exist even in the hardest of hearts.
A young boy smiling | Source: Midjourney
“Josephine!” he called out, his voice brewing with emotion. “Go tell Mom we’re going to the doctor today. And then… maybe we’ll stop for ice cream on the way home. Get Mom a new comfy mattress. And lots of groceries for the entire week!”
As Josephine’s delighted squeals filled the air, Martin clutched the note to his chest. He had remembered, and in doing so, he had found a way forward.
Side view of a happy boy | Source: Midjourney
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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