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 Neighbor Totally Ruined My Windows with Paint after I Refused to Pay $2,000 for Her Dog’s Treatment
An increasingly heated argument starts when Julia declines to pay her neighbor $2000 for a small dog accident. Julia is dealing with family issues and navigating the chaos as tensions grow. But Julia loses it and plans some heinous retaliation after her neighbor paints over her windows.
Allow me to share with you the story of the moment I nearly went insane while residing in a quiet suburban neighborhood.
I’m Julia, and I shared this sweet small home with my husband Roger and our ten-year-old son Dean for more than 10 years.
As long as you disregarded the ongoing concern for Roger’s well-being, everything was fairly wonderful. However, when Linda moved in next door, everything was different.
Linda. The mere thought of her makes my blood boil. We never got along from the day she came in with her golden retriever, Max.
At first, it was simply small things, like her loud music or the fact that she allowed Max go anywhere he wished, nothing serious. However, things took a bad turn one sunny afternoon.
Max came running over to me while I was cutting my roses in my backyard, wagging his tail like he owned the place. Really sweet dog, but intrigued. He took in certain scents, and before I knew it, he yelled.
The poor creature has a little thorn embedded in his paw. I bent down, comforted him, and carefully pulled the thorn out. I patted Max’s head after he licked my fingers.
I accompanied him back to Linda’s, perhaps anticipating a thank you. Rather, she merely stood there, frowning and with her arms crossed.
Why does my dog have a limp? How did you act? She lost her temper.
“He simply trod on a small thorn,” I retorted, attempting to remain composed. “I removed it, and he seems OK.”
She gave a huff, and I assumed that was it. How incorrect I was!
One morning, I discovered a message affixed to my door. “You owe me $2000 for Max’s treatment,” it said.
I was astounded as I stared at it. Two thousand dollars? For what purpose? The dog only received a small cut. I made the decision to visit and make everything clear.
Linda, what’s the deal? I asked, pointing to the message.
Her tone was cold as she continued, “That’s for Max’s vet bill.” “That thorn caused him pain all through the night.”
“I apologize, but that is absurd,” I answered. “As a gesture of goodwill, I’ll give you $100, but two thousand is out of the question.”
Linda squinted her eyes. “You’ll regret it or you pay up.”
Linda turned my life into a living misery the moment she met me.
Every time she drove by, she would flip me off, honk, and tip over my trash cans. Her attempt to have Dean arrested was the worst. Dean, my sweet, naive boy, was simply riding a minibike like all the other kids in the area.
I was enjoying a cup of tea on the veranda one afternoon when I heard Linda’s car horn familiarly screaming. Glaring at Dean, who was playing in the driveway, I looked up.
She said, “Get that brat off that bike before I call the cops!”
“Linda, these are only children!” Feeling my patience wane, I yelled back.
She shot back, “Your kid is a menace, and if you don’t do something about it, I will.”
I was unable to yell, weep, or take action, even though I wanted to. Since Roger was back in the hospital, I was already overburdened with trying to keep things together. Taking a deep breath, I looked up at Dean.
I kindly murmured, “Come inside, honey.” “We’ll switch up the game.”
With tears in his eyes, Dean argued, “But Mom, I didn’t do anything wrong.”
“I understand, my love. Simply put, it’s complicated.
I made an effort to ignore Linda’s shenanigans and concentrate on Roger and Dean. However, it felt as though a ticking time bomb was nearby. I was always afraid of what she might do next. Finally, she pushed me over the edge.
I got the call in the afternoon of a Sunday. Roger’s condition had gotten worse, and I had to head to the hospital right away.
After gathering our belongings, I dropped Dean off at my mother’s house and hurried to the hospital.
I stayed by Roger’s side for two excruciating days, not eating or sleeping, my mind racing with worry and tiredness.
Upon my return, all I wanted was a little break, an opportunity to regain my composure.
Upon walking up my driveway, I discovered that my house had been turned into a nightmare for graffiti artists. Paint in the colors red and yellow spattered my windows, dripping in unkempt streaks.
My house appeared to have been attempted to be converted into a circus tent. And there it was, Linda’s note “Just to make your days brighter!” sitting on the doorstep!
A house covered with paint splatters | Source: Midjourney
I was shaking with fury as I stood there, my fatigue from the previous two days melting away in the fire of my fury. That was it. This was the tipping moment.
I clinched my teeth and whispered, “Dean, go inside.”
“But Mom, what took place?” His eyes wide with terror and perplexity, he questioned.
I said it again, softly this time, attempting to maintain my composure. “Just go inside, honey.”
Dean gave a nod and rushed inside, leaving me to harbor my rage on my own.
With my thoughts racing, I crumpled Linda’s paper in my hand. It had to end. Linda was going to get a war if that was her desire.
I took a drive to the hardware shop that afternoon. I strolled through the aisles, my rage melting into a detached, analytical concentration. When I saw the Japanese Beetle traps, a strategy started to take shape.
I purchased multiple packets of the beetle-attracting smell lures and traps. I put the aroma packets in the freezer as soon as I came home. The wax would be easier to work with in the cold. Anxiety mixed with excitement caused my heart to race. This needed to function.
I slipped into Linda’s yard at three in the morning while the neighborhood was silent due to the darkness.
I had the impression of a figure from one of Roger’s favorite spy films. My heart leaped at the sound of every distant leaf rustle. However, I was adamant. I hid the smell packets behind the layers of mulch in Linda’s well-kept flower beds.
By the time I was done, the first rays of morning were appearing.
I crept back inside my house, feeling my heartbeat finally begin to settle down. Despite being tired, I felt a sense of somber fulfillment as I got into bed. It was now a matter of waiting.
When I looked out my window the following afternoon, I noticed swarms of Japanese beetles descending on Linda’s garden. They were glinting in the sunlight. It was functioning.
Her lovely flower gardens were completely destroyed over the course of the following few days, the once-vibrant blossoms reduced to frayed remains.
Allow me to correct the information. Hi there, my name is Linda, and I came to this area in search of solitude.
My golden dog, Max, went into Julia’s yard by mistake and snagged a thorn in his paw, shattering that fantasy. She pulled it out as if she were doing me a favor, rather than just giving it back to him.
I asked Julia to pay Max’s vet bill the following day.
He was in discomfort and walking with a limp all night. However, she was so bold as to offer me just $100 rather than the $2000 it would have cost. I told her she would regret not paying up after our argument. Things didn’t seem to be getting out of control.
Yes, I did, a couple times knocked over her trash cans and honked as I went past, to let her know I wasn’t going to back down. However, Julia painted myself as the bad guy.
I didn’t know things had gotten out of hand until insects decimated my garden.
I was like a crazy woman, rushing around my yard. When I was picking away dead flowers on the third day, I noticed something strange hidden in the mulch. When I saw that it was a piece of plastic packaging—part of a Japanese beetle trap—my heart fell.
Someone had intentionally done this. And I knew who it was, very well.
My wrath blazing, I stormed straight to Julia’s house. I knocked on her door, presenting the proof that implicated her.
“Julia! Let yourself in!” I yelled, fury trembling in my voice.
Appearing composed as ever, she unlocked the door. “What’s going on, Linda?”
“You know what you did to my garden?” I threw the plastic fragment towards her. This was discovered in my flower bed. Yes, you did this, right?
Although Julia maintained a neutral expression, there was a hint of something—guilt, perhaps—in her eyes. “Lucina, I have no idea what you’re talking about.”
“Don’t tell me lies!” I let out a cry. “You destroyed my yard! Why would you act in this manner?
A wail sounded from within the home before she could respond. When I looked behind Julia, I noticed Dean, her son, seated on the floor with tears running down his face.
“Is Dad going to pass away, Mom?” With his tiny voice breaking, Dean cried.
Julia looked past me, her expression softening as she turned to greet her son. “No, sweetheart, everything will be OK. The medical professionals are exerting every effort.
I watched this scene play out while freezing in place. My rage seemed so trivial now.
Julia was more than simply my obnoxious neighbor; she was a mother taking care of her sick husband and her afraid child.
“Julia, I.” I opened my mouth, but my words stumbled. How do I put it? I hadn’t paused to think about what she might be going through since I was so overwhelmed by my rage.
With a look of fatigue on her face, Julia turned to face me. “Linda, I apologize for your garden. However, I didn’t do it. I can’t handle this anymore, let alone caring about your flowers.
My fight was gone from me. “I apologize too,” I said. “I had no idea that things were so horrible for you.”
She gave a nod, remaining silent. I recoiled, embarrassed by my own foolishness. How could it have gotten so out of control?
That being said, I kept to myself. I realized that Julia had enough on her plate and put an end to the small-time harassing. My garden recovered slowly, and although Julia and I never became friends, we were able to live in harmony together.
I still think about that period of time years later. Sometimes, in order to understand what others are going through, you have to look past your own problems. Even though Julia and I have remained estranged neighbors, we have a silent respect for one another that was developed through hardship.
Though it has been romanticized for artistic purposes, this work draws inspiration from actual individuals and events. For reasons of privacy protection and story improvement, names, characters, and details have been changed. Any likeness to real people, alive or dead, or real events is entirely accidental and not the author’s intention.
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