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
Disguised as a Cleaner, a Journalist Faces the Unexpected When a Millionaire Recognizes Her Pendant – Story of the Day
Laura believed that her writing could change the world. But reality turned out differently, and her boss pushed her to dig up dirt on famous people. Desperate to save her job, she disguises herself as a cleaner to get compromising details on a millionaire. However, she uncovers a life-changing truth in the process.
The office hummed with the familiar sounds of keyboards clicking, phones ringing, and the occasional burst of laughter from a distant corner.
Laura sat at her desk, papers scattered around her, but her focus was elsewhere.
Her thoughts were interrupted when Reggie, the editor-in-chief, stepped out of his office.
His eyes scanned the room until they landed on her. He looked tired—more tired than usual—and his face carried the weight of disappointment.
For illustration purposes only. | Source: Midjourney
“Laura… come to my office for a minute,” he said. His tone was calm but firm. He held the door open, waiting for her to follow.
Taking a deep breath, Laura rose from her chair and walked toward Reggie’s office, each step feeling heavier than the last.
“Sit down,” Reggie said, gesturing to the chair across from his desk.
“Reggie, I was just about to tell you about a new article I’m working on,” she began, trying to sound upbeat. “It’s about the chemical pollution in a nearby lake—”
For illustration purposes only. | Source: Midjourney
“That’s exactly what I wanted to discuss with you,” Reggie cut in, sighing as he sank into his chair. He folded his hands and looked directly at her.
“Laura, pollution in forests, lakes, the extinction of… what are they called again?”
“California condors,” Laura said, her tone sharp.
“Condors, yes.” He nodded.
“People don’t care about this stuff, Laura. They don’t read it. And it’s not just my opinion—the data backs it up.”
For illustration purposes only. | Source: Midjourney
Laura’s brow furrowed. “But people should care, Reggie! This isn’t just about nature; it affects our health, our communities—everything!”
Reggie leaned forward, his voice hardening.
“It doesn’t bring in money. We all need to eat. Salaries need to be paid, and I can’t pay someone who isn’t generating revenue.”
Reggie softened his tone, removing his glasses and rubbing his temples.
For illustration purposes only. | Source: Midjourney
“I like you, Laura. You’re talented, and you care about your work. That’s why I’m trying to help you.”
“How?”
Reggie slid a photograph across the desk. It showed an elderly man with a stern expression.
“This is Mr. Weiss,” Reggie said. “You know who he is, don’t you?”
“A wealthy man,” Laura murmured, studying the image.
“The wealthiest man in the city,” Reggie corrected.
For illustration purposes only. | Source: Midjourney
“Rumor has it he’s been spending tens of thousands on private investigators. Years of it.”
“And?” Laura asked, confused. “It’s his money. Why does that matter?”
“Why would an old man need private investigators?” Reggie leaned back, a sly smile forming.
“Mistresses, scandals, maybe even crimes. Find anything—and I mean anything—about his expenditures, and spin it into a story. This could be the article that saves your career.”
Laura hesitated. “And if I can’t?”
For illustration purposes only. | Source: Midjourney
Reggie’s smile faded. “Then I’d recommend you start looking for another job.”
The cold air nipped at Laura’s cheeks as she stood in front of the grand estate, its towering gates and sprawling lawn exuding wealth and history.
Taking a deep breath, she straightened her shoulders and rang the doorbell.
The heavy wooden door creaked open slowly, revealing an elderly man. His figure was slightly hunched, his face marked by deep lines of exhaustion.
For illustration purposes only. | Source: Midjourney
Dark circles framed his eyes, and his scruffy beard looked like it hadn’t been groomed in days.
“Good morning, Mr. Weiss,” Laura said with a polite smile that she hoped masked her nerves.
“My name is Laura. We spoke on the phone about the cleaning position.”
“Good morning,” Mr. Weiss replied, his voice quiet and tinged with weariness. “Come in. Forgive the mess; there’s plenty of work to keep you busy.”
Laura stepped inside, her eyes widening as she took in the space.
For illustration purposes only. | Source: Midjourney
A thick layer of dust covered the once-pristine surfaces, cobwebs adorned the corners, and books and papers were scattered haphazardly across the rooms.
“As you can see,” Mr. Weiss continued, “I really need the help. Start wherever you’d like. I’ll be in my study.”
With that, he turned and shuffled away, closing the study door behind him.
“Thank you for the opportunity, Mr. Weiss,” Laura called after him, but he didn’t respond.
Through the brief crack before the door shut, Laura glimpsed his desk. It was cluttered with papers, photographs, and what looked like old receipts.
For illustration purposes only. | Source: Midjourney
Her heart raced—this could be where the secrets were buried.
Laura spent the next hour cleaning the house, her movements mechanical as her mind churned with plans.
Finally, she approached the study door and knocked softly. “Mr. Weiss, I’m coming in to clean—”
“No!” His voice was startlingly sharp as the door opened just enough for him to peer out.
“The study doesn’t need cleaning. Thank you for your work today. If you’ve finished the other rooms, you’re free to leave.”
For illustration purposes only. | Source: Midjourney
“There are still a couple of rooms left,” Laura replied, feigning disappointment, but her mind was already racing.
The study was off-limits, and she was more determined than ever to find out why.
Laura crouched near the sofa, her heart racing.
She glanced toward the study door, still closed, as her mind raced through the plan one more time.
It wasn’t elegant, but it might work. Taking a deep breath, she screamed, her voice sharp and filled with faux terror.
“Aaaaah! Mr. Weiss! Help!”
For illustration purposes only. | Source: Midjourney
The sound of hurried footsteps echoed down the hallway. Moments later, Mr. Weiss appeared, his face a mask of alarm.
“What happened?” he demanded, clutching the edge of the doorway.
“There’s a rat!” Laura cried, pointing under the couch with a trembling hand. “It just ran under there! Please, I can’t stand rats—they terrify me!”
“A rat?” Mr. Weiss frowned, his brow furrowing.
“That’s impossible.” He grabbed a broom leaning against the wall and knelt to peer under the couch.
For illustration purposes only. | Source: Midjourney
“Where? I don’t see anything. Did it run out?” he asked, poking around with the broom handle.
“I… I don’t know!” Laura stammered, backing toward the hallway. “Just keep looking. I’ll hide in the kitchen!”
Mr. Weiss grumbled but continued his search, muttering to himself about how unlikely it was.
As soon as he was fully distracted, Laura moved quickly. She slipped into his study, closing the door as quietly as possible.
The room was dim, illuminated only by a small desk lamp. Papers were strewn across the desk—receipts, handwritten notes, and photographs.
For illustration purposes only. | Source: Midjourney
Laura’s journalist instincts kicked in as she pulled a small camera from her pocket and took pictures.
Her hands trembled as she worked quickly, her breath shallow.
Then she saw it. Among the scattered documents was a detailed sketch of a medallion.
She froze, her pulse hammering in her ears.
Reaching for her necklace, she pulled the small pendant from under her blouse and held it next to the sketch. They were identical.
For illustration purposes only. | Source: Midjourney
“Laura.”
The low, heavy voice sent a chill down her spine. She turned to see Mr. Weiss standing in the doorway, his face shadowed.
“I told you not to come in here,” he said, his voice filled with a mix of anger and pain.
Her hand instinctively clutched the pendant. Mr. Weiss’s eyes widened as he stepped closer, his gaze fixed on the pendant.
“Where did you get that pendant?” he asked, his voice trembling. He reached out, his hand shaking as he touched the necklace.
For illustration purposes only. | Source: Midjourney
“Tell me! Where?”
“It was my mother’s,” Laura snapped, pulling back.
“Your mother…” Mr. Weiss whispered, his face pale. “Was her name Dora?”
Laura’s breath caught. “Yes. How do you know that?”
Mr. Weiss’s knees buckled, and he sank to the floor. Tears welled in his eyes as his voice broke.
“Dora… my sweet Dora. She had a daughter…” He looked up at Laura, his expression filled with anguish. “Forgive me. Please forgive me.”
For illustration purposes only. | Source: Midjourney
Laura staggered back, her hand gripping the desk for support. “You knew my mother?”
“I’m your father,” Mr. Weiss said, his voice raw with emotion.
The words hit her like a blow. “You left her!” she cried, tears streaming down her face.
“You abandoned her—and me! She struggled every day because of you!”
“I know,” he said, his voice barely audible.
“I was a coward. I was afraid of responsibility, afraid of being a father. I’ve regretted it every day. I tried to find her, but she cut all ties. Tell me—where is she now?”
For illustration purposes only. | Source: Midjourney
“She’s gone,” Laura spat bitterly.
“She died ten years ago. She got sick, and it’s your fault. She fought so hard to survive, but she was alone because you weren’t there.”
Mr. Weiss crumpled, his body wracked with sobs.
“I never stopped looking. I never stopped loving her. I’m so sorry, Laura. I’m so sorry.”
Laura stared at him, her chest heaving with anger and pain. She shook her head, grabbing her bag.
For illustration purposes only. | Source: Midjourney
“I can’t do this,” she said, her voice trembling as she turned and fled the room.
The sound of his sobs followed her as she ran through the grand house and out into the cold night.
Later, Laura sat in the newsroom, her fingers hovering over the keyboard.
The photographs lay beside her, their edges curling slightly under the pressure of her hand.
On her screen, the half-written article glared back at her. This story would blow up—it would ruin Mr. Weiss’s name, tarnish his legacy, and save her job.
For illustration purposes only. | Source: Midjourney
But as she stared at the photos, her chest tightened. Anger and doubt battled in her mind.
Could she really destroy him after everything she had learned? He wasn’t just a stranger anymore. He was her father.
Summoning her courage, Laura stood and walked into Reggie’s office. Her breath felt heavier with each step.
“Reggie, can I come in?”
“Of course,” Reggie said, leaning forward with anticipation. “Please tell me you’ve got something good.”
For illustration purposes only. | Source: Midjourney
Laura placed a photograph on his desk. “The article is ready. I can send it over now.”
Reggie’s eyes gleamed as he examined the picture. “This is perfect, Laura! A millionaire’s dirty secrets—this is going to be huge!”
Laura’s hands trembled. Reggie’s words felt like nails on a chalkboard.
“No,” she said suddenly, grabbing the photo back. Without thinking, she ripped it into shreds and tossed them into the air.
“What are you doing?” Reggie roared, his face turning red.
For illustration purposes only. | Source: Midjourney
“I won’t ruin his life. If that’s what this job takes, I don’t want it,” Laura said, her voice steady.
“You’re fired!” he shouted.
Laura walked out, her head held high. She had lost her job, but she had found something far more valuable—her integrity.
And for the first time in years, she had a family worth fighting for.
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: “All men are liars.” With these words, Violet ended her radio program. Her life experiences and the countless stories she heard from her listeners had proven it. But, a date with a coworker made her question her belief. After a call from a stranger, she was convinced she had been right all along.
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.
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