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
Old Woman Brought Son’s Favorite Pastry to His Grave & Found Note Saying ‘Thank You’ upon Her Return – Story of the Day
For Nancy her son Henry was everything, she never imagined her life without him. It had been 23 years since the horrible accident that took Henry’s life. Every year on that day, she took his favorite pie to his grave to honor his memory. But this year, everything was about to change.
For 23 years, Nancy, now 61, never missed a single day on this date. She baked her late son’s favorite pie and took it to his grave every year since.
The pie, a simple yet delicious apple and cinnamon creation, had been Henry’s favorite since childhood.
The scent of apples and cinnamon brought back memories of when Henry was little, running into the kitchen, his eyes lighting up at the sight of the pie.
For illustration purposes only. | Source: Midjourney
It was his favorite dessert, and baking it had become a tradition they both cherished.
Since Henry’s tragic accident at 17, this ritual had been Nancy’s way of keeping his memory alive.
It gave her a sense of connection to him, like she was still doing something special for her boy. Losing him had been the hardest thing she had ever gone through. The pain of that day never left her.
Even though the years had passed, her grief remained, only softened by time and the small comfort this tradition brought her.
For illustration purposes only. | Source: Midjourney
On this particular day, just like every year before, Nancy carefully carried the freshly baked pie to the graveyard.
The weight of the dish felt heavier, as it always did when she walked toward Henry’s resting place. The grave was neat and covered in flowers, a sign of how much he was still loved.
The stone had become smoother over the years, as she had often run her fingers over it, lost in her memories.
Nancy knelt, placing the pie gently on the gravestone. Her heart ached as she began to speak, her voice quiet, as though Henry might somehow hear her.
For illustration purposes only. | Source: Midjourney
“Henry, I hope you’re at peace, my love. I miss you every day. I baked your favorite pie again. Remember how we used to bake it together? You’d always sneak a taste before it was done.”
She smiled, but her eyes were misty with tears. “I wish we could do that one more time.”
The familiar sorrow welled up inside her, but Nancy had learned over the years to push through the tears.
For illustration purposes only. | Source: Midjourney
She wiped her eyes quickly and managed a small smile. After a few more moments of silence, she kissed her fingers and touched the top of the gravestone as she said her quiet goodbye.
Then, with a heavy but comforted heart, she turned and walked away, knowing she’d be back next year, just like always.
The next day, as part of her routine, Nancy made her way back to Henry’s grave to clean up the remains of the pie.
For illustration purposes only. | Source: Midjourney
Usually, by the time she returned, the pie was either untouched or spoiled by the weather, a quiet reminder of her son’s absence.
She had always found it a bittersweet comfort, knowing the pie stayed where she left it as if waiting for him.
But today, as she approached the grave, something felt different. Nancy’s heart skipped a beat when she saw that the plate was clean—completely empty. For a moment, she stood frozen in disbelief.
Then, she noticed something else. Resting on the plate was a small piece of paper, folded in half.
For illustration purposes only. | Source: Midjourney
Nancy’s hands trembled as she picked up the note. Her breath caught in her throat as she unfolded it.
The handwriting was shaky, as though whoever had written it had struggled to form the letters. The simple words read: “Thank you.”
Her heart pounded with confusion and anger.
“Who would take Henry’s pie?” she muttered under her breath, clutching the note tightly. “This was for my son. No one had the right to touch it!”
For illustration purposes only. | Source: Midjourney
Her private ritual, her way of honoring and remembering her son, had been invaded by a stranger.
She felt violated, as if someone had stolen a piece of her grief.
With her emotions swirling—part outrage, part confusion—Nancy left the cemetery, her mind set on finding the person who had taken her son’s pie. She had to know who had done this, and why.
Determined to catch the culprit, Nancy decided she would take matters into her own hands. She couldn’t let someone continue to disturb the way she honored Henry. So, she devised a plan.
For illustration purposes only. | Source: Midjourney
That night, she baked another of Henry’s favorite pies, the same apple and cinnamon recipe she had been making for over two decades.
The next morning, with renewed resolve, she placed the freshly baked pie on Henry’s grave, just like before, but this time she wasn’t leaving.
She found a large oak tree nearby and hid behind it, close enough to see the grave but far enough to not be noticed.
For illustration purposes only. | Source: Midjourney
The warm aroma of the pie drifted through the air, filling the quiet cemetery.
Time passed slowly as Nancy watched and waited, her heart racing in anticipation.
An hour later, she spotted movement. A small figure cautiously approached the grave. Nancy squinted, leaning forward to get a better look.
It wasn’t the greedy thief she had imagined. No, this was something entirely different.
For illustration purposes only. | Source: Midjourney
A young boy, no older than 9, with ragged clothes and dirt smudged on his face, moved toward the pie with hesitant steps.
Nancy’s heart tightened as she watched him. The boy didn’t immediately take the pie.
Instead, he knelt by the grave and reached into his pocket, pulling out a small scrap of paper and a dull pencil. His hand trembled as he carefully scribbled something on the paper, his brow furrowed with concentration.
It was clear the boy struggled with writing, but he took his time, making sure each word was legible.
For illustration purposes only. | Source: Midjourney
Nancy’s heart softened as she saw him write “Thank you” on the paper, just like before. He wasn’t a thief. He wasn’t someone disrespecting Henry’s memory. He was just a hungry child, grateful for the kindness of a pie left behind.
The anger that had once consumed Nancy melted away in an instant. She realized this boy wasn’t stealing; he was surviving. He was in need, and her son’s favorite pie had somehow brought him comfort.
As the boy began to pick up the pie, his small hands shaking, Nancy stepped out from her hiding spot.
For illustration purposes only. | Source: Midjourney
The rustle of leaves under her feet made him freeze, wide-eyed. Startled, he dropped the pie, and it tumbled onto the grass. His face paled, and he backed away, looking terrified.
“I’m sorry, I’m really sorry!” the boy cried, his voice trembling with panic. “I was just so hungry, and the pie was so good. Please don’t be mad.”
Nancy’s heart softened instantly. The sight of him—thin, dirty, and scared—erased any trace of anger she had felt before.
For illustration purposes only. | Source: Midjourney
She knelt beside him, speaking gently, her voice as comforting as she could make it. “It’s alright, sweetheart. I’m not mad at you, Where are your parents?” she said, her tone soothing. The boy stayed silent and shook his head. “What’s your name?” Nancy asked another question understanding that the boy had nowhere to go.
“Jimmy,” he muttered, still avoiding her eyes, ashamed of what he had done.
“Well, Jimmy,” Nancy smiled softly, trying to reassure him, “it’s okay. You don’t have to steal pies. If you’re hungry, all you had to do was ask.”
For illustration purposes only. | Source: Midjourney
Jimmy looked up at her, his lips quivering as he tried to speak. “I didn’t mean to steal,” he said, his voice small and shaky. “I just… I don’t get to eat much, and that pie was the best thing I’ve ever had.”
Nancy’s heart ached for him, her mind flooded with thoughts of how different this boy’s life must be.
The hunger in his eyes reminded her of her own son, Henry, when he would eagerly wait for that first bite of her freshly baked pie.
But Henry never had to worry about where his next meal would come from. Jimmy, on the other hand, looked like he had been living with hunger for a long time.
For illustration purposes only. | Source: Midjourney
“Come with me,” Nancy said after a moment of thought. She stood up and reached out her hand to him. “I’ll bake you a fresh pie, just for you.”
Jimmy’s eyes widened in disbelief, as if he couldn’t trust his own ears. “Really?” he asked, his voice filled with a mix of hope and doubt.
Nancy nodded, her heart filled with a strange but comforting warmth. “Yes, really. You don’t have to be afraid.”
Slowly, Jimmy reached out and took Nancy’s hand.
For illustration purposes only. | Source: Midjourney
She led him back to her home, the boy walking beside her in silence, his eyes darting around as if he wasn’t sure if this was all real. Nancy’s heart swelled with the thought of what she was about to do.
Baking had always been her way of expressing love, and now, after years of baking for a son she could no longer see, she was about to bake for someone who truly needed it.
When they reached her cozy kitchen, Nancy set to work, rolling out the dough, slicing the apples, and adding the perfect amount of cinnamon—just as she had done so many times before.
For illustration purposes only. | Source: Midjourney
Jimmy watched her quietly from the corner of the kitchen, his eyes wide as he followed every move she made.
The smell of the pie began to fill the room, warm and comforting, like a hug from a long-lost friend.
Once the pie was baked, Nancy placed it in front of Jimmy. “Here you go, sweetheart,” she said softly.
“This one’s all for you.”
Jimmy hesitated for a moment, as if he couldn’t believe what was happening. But then he grabbed a slice and took a bite. His face lit up with joy, his eyes sparkling as he chewed.
For illustration purposes only. | Source: Midjourney
“This is the best pie I’ve ever had,” he said, his mouth still full. He ate with such happiness that it brought tears to Nancy’s eyes.
She watched him in silence, thinking about how something as simple as a pie could bring so much comfort to someone.
As Jimmy devoured the warm slices with obvious delight, Nancy couldn’t help but think of Henry.
She had always dreamed of seeing her son eat his favorite pie again, of watching him enjoy it the way he used to when he was a child.
For illustration purposes only. | Source: Midjourney
But now, in some strange and unexpected way, she was sharing it with another boy who needed it just as much.
Watching Jimmy eat, Nancy felt a deep sense of peace wash over her. Perhaps this was how it was meant to be.
Maybe fate had brought Jimmy into her life for a reason. By feeding him, by offering him kindness when he needed it most, she was honoring Henry’s memory in a way she had never imagined.
For the first time in years, Nancy felt that her grief had led her to something beautiful—a connection, a purpose that gave new meaning to her life.
For illustration purposes only. | Source: Midjourney
Maybe, just maybe, this was Henry’s way of sending her a message—that love and kindness should always find their way back to those in need.
Nancy smiled as she watched Jimmy finish the last slice of pie, her heart full of warmth and gratitude.
She had found an unexpected connection in the most unlikely place, and it filled her soul in a way that nothing else had in years.
Tell us what you think about this story, and share it with your friends. It might inspire them and brighten their day.
If you enjoyed this story, read this one: Martha was always quiet and smiling. No matter how hard or small the task, she was always ready to help. One of her colleagues, Chelsea, often took advantage of Martha’s kind nature by asking her to do her work for her. But this time, Chelsea unintentionally did Martha a favor.
This piece is inspired by stories from the everyday lives of our readers and written by a professional writer. Any resemblance to actual names or locations is purely coincidental. All images are for illustration purposes only. Share your story with us; maybe it will change someone’s life.
Leave a Reply