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
My Sister Asked Me to Babysit Her Daughter, but Hours before She Returned, I Realized the Child Was Missing – Story of the Day
Every man reaches a moment when he wants to settle down and have a loving family. But not Henry—he was convinced he would stay single forever, believing it was the better life for him. However, a day with his nine-year-old niece makes him realize the true reason behind his choices.
The morning light filtered through unfamiliar curtains, and I woke up to the sensation of something warm and wet on my face.
It was a dog—not mine—a small, fluffy creature with wide, eager eyes that seemed to say, You’re mine now.
It licked my cheek persistently, wagging its tail with determination. Did it want food? A walk? Who knew?
As I rubbed my eyes, the events of the previous night slowly returned. I turned my head and saw her—a girl I’d met at the club.
For illustration purposes only. | Source: Midjourney
She was asleep, her hair sprawled across the pillow.
This wasn’t my place. If I was here, that meant I’d accomplished what I’d set out for.
And now it was time to do what I always did: gather my things and make a quiet exit.
I slipped out of bed carefully, scanning the room. There were my pants, crumpled on the floor. My shirt hung awkwardly off a chair.
One sock sat beside my shoe, but the other… where was it? My search led me to the dog’s mat.
For illustration purposes only. | Source: Midjourney
There it was, claimed by the little fluffball now wagging its tail with pride.
I crouched down, whispering,
“Hey, buddy, that’s mine.” I reached for the sock, but the dog grabbed it with its teeth, growling playfully.
Just as we began our tug-of-war, a groggy voice broke the silence.“Henry? Are you up already?”
I froze. She was awake. Turning, I saw her smiling at me with sleepy eyes.
“Uh, yeah,” I stammered, “I’ve got work. Running late for a meeting.”She frowned.
For illustration purposes only. | Source: Midjourney
“But it’s Saturday…”
“I work weekends sometimes. Important stuff, you know.”
Her smile faded, replaced by a curious tilt of her head.
“So… will I see you again?”
“Of course,” I lied smoothly. “I’ll call you.”Her brow furrowed.
“You’ll call me? Did I even give you my number?”
For illustration purposes only. | Source: Midjourney
Uh-oh. Panic swirled in my chest.
“I thought you did. Didn’t you?”
“And how did you save my name?” she pressed.
Caught, I stammered, “By your name, obviously.”
Her gaze sharpened.
“And what’s my name?”
For illustration purposes only. | Source: Midjourney
I swallowed hard. Two options: admit the truth or …
“Nancy?” I guessed weakly.
Her face darkened instantly.
“Get out of here! I knew it! You’re just like the rest—ugh!”
Slippers flew in my direction as I grabbed my jacket and shoes, dodging her fury all the way out the door.
Sitting in my car, I leaned back and sighed. The rearview mirror reflected a face that looked satisfied, smug even.
For illustration purposes only. | Source: Midjourney
This was my life: no strings, no responsibilities, just freedom. Who needed the hassle of a family? Not me.
While others tied themselves down, I lived for the thrill—parties, work, and the kind of independence most people only dreamed about.
A loud ringtone interrupted my thoughts. I glanced at the screen and blinked. Riley? My sister hardly ever called. I hesitated before answering.
“Hello, Riley?”
For illustration purposes only. | Source: Midjourney
“Henry,” she said, her voice tight, “I need to talk to you. Got a minute?”
I frowned. “Sure. What’s going on?”
“Come over as soon as you can. I can’t explain over the phone. When can you get here?”
“Fifteen minutes. Is everything okay?”
“Just come. I’ll explain.”
I stared at the phone for a moment, then started the car. Whatever this was, it had to be serious.
For illustration purposes only. | Source: Midjourney
Twenty minutes later, I pulled into her driveway and barely made it to the door before it swung open.
Riley stood there, arms crossed, her expression a mix of annoyance and urgency.
“You’re late!”
“By five minutes,” I retorted, stepping inside.
“Relax, Riley. You don’t have to be such a pain in the…”
“Don’t swear,” she hissed. “My daughter’s nearby.”
For illustration purposes only. | Source: Midjourney
I followed her gaze and saw Mira, her nine-year-old, curled up on the couch with an encyclopedia.
Her tiny face was scrunched up in concentration, her finger tracing the lines of text like a mini scholar.
“As expected, you’re my last option,” Riley said with a sigh. “I need you to watch Mira today.”
“Me? Are you serious?” I asked, glancing nervously at Mira, who hadn’t looked up from her book.
“I wouldn’t ask if I had another choice,” she said, exasperated.
“I have a business dinner tonight. Either I go and close this deal, or I cancel because I can’t leave her alone. Can you help me or not?”
For illustration purposes only. | Source: Midjourney
“Fine,” I muttered. “If it’s that important.”
“Great. Food’s in the kitchen. I left money in case you need to order something, but keep it healthy. No greasy junk. And she’s not allowed outside. Got it?”
“Got it.”
With a quick goodbye, Riley was out the door, leaving me and Mira alone. I looked at her. She looked at me.
Neither of us said a word. Let the longest day of my life begin.
For illustration purposes only. | Source: Midjourney
The day dragged on like an endless loop of boredom.
Mira sat on the couch, clutching her encyclopedia, and occasionally glanced at me with a look that made me feel like a failing science experiment.
Her small face was calm, but her raised eyebrows screamed judgment.
I cleared my throat.
“So, uh, you like reading?” I asked, trying to break the awkward silence.
For illustration purposes only. | Source: Midjourney
“Yes, I do. Mom says books are knowledge, and I want to know a lot,” she said, her voice cool and sharp, like a character straight out of a movie about child prodigies.
I nodded. “Cool, cool… What’s your favorite subject in school?”
Mira sighed, looking at me as if I’d just asked the world’s most boring question.
“That’s such an unoriginal question, but I’ll answer anyway. I like biology because it has lots of animals, and I love learning about them.”
For illustration purposes only. | Source: Midjourney
“Cool,” I mumbled, unsure what else to say. Conversations with kids were harder than I thought.
After a moment, she closed her book and tilted her head. “So, are you my uncle?”
“Yeah,” I replied. “You probably don’t remember me, though. We met when you were little.”
“Got it,” she said simply. Then she hit me with a curveball. “Are you married?”
“Uh, no. I’m not married.”
“Why not?” she asked, her curious tone sounding more like an interrogation.
For illustration purposes only. | Source: Midjourney
“I don’t want to get married. I like being on my own,” I said, hoping that would end the conversation.
“No one likes being alone,” she replied, crossing her arms.
“I do,” I insisted, though her words stung more than I cared to admit.
“Maybe you’re scared,” she said matter-of-factly.
“Scared? What would I be scared of?”
“Mom says marriage is a lot of work. She also says you don’t like working. So maybe you’re scared of hard work.”
For illustration purposes only. | Source: Midjourney
I sat up straight.
“She told you that!? Well, just so you know, I’m not scared! Maybe it’s just… not for me. For now.”
“Got it. You’re scared,” Mira concluded, her lips curling into a tiny smirk. “Anyway, I’m hungry.”
“Then eat something,” I said, gesturing toward the kitchen.
“Mom said you’re taking care of me. So take care of me,” she shot back.
“Fine,” I muttered, opening the fridge. It was full of salads, juices, and not a single thing I wanted to eat. I sighed and pulled out my phone.
For illustration purposes only. | Source: Midjourney
“Pizza it is,” I declared.
Minutes later, we were sitting on the couch, devouring slices while watching TV. Mira was quiet for once, her face lit up by the screen.
Before I knew it, my head rested against the back of the couch, and the exhaustion of the day caught up with me. I didn’t even notice when I drifted off to sleep.
I woke up with a jolt, blinking against the light streaming into the room. Something felt off. The house was too quiet. I glanced around, and that’s when it hit me—Mira was nowhere to be seen.
For illustration purposes only. | Source: Midjourney
“Mira!” I called out, my voice echoing through the house. “Mira, where are you?”
No answer.
Panic surged through me. I started tearing through the house, opening doors, peeking under beds, and even checking the closets and cupboards.
Every empty space mocked me. My heart raced faster with each passing second.
I had one job. One simple job. Watch Mira for a day, and I couldn’t even manage that.
For illustration purposes only. | Source: Midjourney
I pulled out my phone, desperate for a clue, and saw a text from Riley:
“On my way home. I’ll be there in an hour. Everything okay?”
I froze for a moment, then typed back: “All good!” It was a lie, but I needed time to fix this.
Running downstairs, I scanned the living room again and noticed something I’d missed earlier: the window.
It was open, and a faint breeze fluttered the curtains. Mira had gone outside.
I crawled through the window and spotted a small shoe lying by the neighbor’s fence. My breath caught.
For illustration purposes only. | Source: Midjourney
Climbing over, I found myself in their backyard, where a tall tree stood with a sturdy wooden treehouse perched near the top.
“Mira!” I yelled, looking up.
“I’m here,” her calm voice replied from above.
I climbed the rickety ladder, my pulse still hammering. At the top, I found Mira sitting cross-legged with another boy.
They were playing with toy figures, completely unbothered.
“Mira! You scared me!” I said, still catching my breath. “Why did you run off like that?”
For illustration purposes only. | Source: Midjourney
“I got bored,” she said, shrugging. “And Sam was here. Sam, say hi to my uncle.”
“Hi, Mira’s uncle,” Sam said, not looking up.
“But your mom said you weren’t allowed outside!”
“She said you were supposed to make sure I didn’t go out,” Mira pointed out, her tone matter-of-fact. “But you were sleeping. Now I know what you’re scared of.”
“Of course I was scared!” I snapped, then softened. “Sorry. But why doesn’t your mom let you play with other kids?”
For illustration purposes only. | Source: Midjourney
“She says I’ll pick up bad habits,” Mira said.
“But I like playing with Sam.”
“There’s nothing wrong with playing with other kids,” I said gently.
“Your mom’s just… protective.”
“And you’re not protective enough,” she quipped with a smirk.
I sighed. “You’re right. From now on, I’ll be more careful.”
For illustration purposes only. | Source: Midjourney
In half an hour, the door creaked open, and Riley stepped into the house, her keys jingling as she set them on the counter. “Mira!? Henry!? Where are you two!?” she called out, her voice bouncing off the walls.
No answer.
The house was dark and eerily silent, with no sign of life. The faint glow of the streetlights seeped through the curtains, casting long shadows that made the empty space feel even more unsettling.
Riley’s heart raced as she scanned the room. “Where are they?” she muttered under her breath, her hands trembling slightly. Her eyes darted to an open window, the curtain flapping lazily in the breeze.
“Oh my god! I knew I shouldn’t have trusted my idiot brother!” she mumbled, panic setting in. She rushed toward the window, her mind racing with worst-case scenarios.
Suddenly—
For illustration purposes only. | Source: Midjourney
“Surprise!!” Mira and I popped up from outside, shouting in unison.
Riley jumped back, clutching her chest. “God! I thought you were both gone! What’s wrong with you two!?”
We burst out laughing, and Mira nearly doubled over with glee. Riley’s face softened as she watched her daughter giggling, her playful spirit infectious.
“Sorry, sis. You were asking for it,” I teased, grinning. “Don’t worry so much. Nothing could go wrong, you’ve got to trust Mira a lot more.”
“Yeah, Mom!” Mira chimed in, beaming.
Riley sighed, a reluctant smile creeping onto her face. “You two are impossible,” she said, pulling Mira into a hug. “But I guess I’ll let it slide this time.”
As I left, I realized something: sometimes, kids teach you things about yourself you didn’t even know you needed to learn.
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: 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 compromising a millionaire. However, she uncovers a life-changing truth in the process.
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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