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
Dad Takes Disabled Daughter to Prom, Finds $10K Check for ‘Dad of the Year’ in Mailbox Later — Story of the Day
A disabled girl who falls behind without a prom date is in for a surprise when her dad takes her to the prom. The reward he gets the next day in recognition of his love for his child transforms their lives.
“Molly, look! Your dad’s here!” someone from the funeral told the 17-year-old girl who was mourning over her mother Daisy’s coffin.
Danny, Molly’s dad, and her mom had divorced ten years ago. Since then, Molly had only heard terrible things about her father—like he was a ‘drunkard’ and such.
Though Molly didn’t have any bitterness towards Danny, she often missed their dad-daughter connection. But after her mom’s funeral, things were going to change for Molly…
“Hey, sweetheart!” Danny greeted his daughter and hugged her before placing a wreath on his ex-wife’s coffin.
“Sir, is that truck yours? It’s blocking half the parking. You mind moving it?” a guest asked Danny, who was a truck driver.
“Yeah, that’s ma truck. Gimme a second. I’ve just met ma daughter. Hope ya understand. Thank ya!”
Danny was delighted to meet Molly. The only link he had with her all these years was through the child support he paid for her. Daisy never allowed him to see Molly because she feared he would become a bad influence.
The funeral was over, and everybody left. Danny packed all of Molly’s stuff and told her they were going to his house.
“A parcel? Who sent it?” he wondered. A card on it read: “For Dad of the Year”
“But why, dad? I can’t leave this house. Mom and I lived here. It’s filled with our memories.”
Molly frowned because Danny wouldn’t listen. He knew he could not leave his daughter alone, particularly considering she often used a wheelchair when she didn’t need crutches. Due to an underlying condition she had developed in her left leg when she was six, Molly limped.
Two days later, Molly moved in with her dad. Though the house was compact and untidy, it comforted her and made her feel loved and included.
As days passed, Danny had difficulty doing things for Molly. Since he never saw her grow up, he did not know how to tackle most things, like braiding her hair, for example. He learned how to do it by watching online videos. But that was not all.
He vacated his bedroom so that Molly would have a nice space to sleep. He even bought a fluffy new bed so that she could rest well. Danny did everything on his end to make his daughter feel at home, but if there was something he kept a secret, it was his constant disappearance at night.
Molly had no idea where her dad had been going at night after she fell asleep. She could only guess he was loitering with his friends in the pub, just as her mother often told her.
A few days later, Molly stepped down from the school bus and entered their home, crying. She found the door was locked. There was a note tucked behind a plant. “The keys are under the pot. I will be back soon. See ya! – Dad.”
Molly scowled and recalled her mother telling her about her dad’s ‘odd’ habits in the evenings. She frowned thinking her father was out drinking at four in the afternoon.
Hours passed, but Danny never returned home. Molly cooked herself pasta, leaving some for her dad. Then she lay on her bed crying.
“If only I was normal, I wouldn’t be the odd one out. I would have found a date for the prom.”
It turned out that Molly’s teacher had informed them about their upcoming senior prom. All her classmates had found prom dates except for Molly. Nobody was interested in taking her. She figured—who would want to dance with someone with a limp?
Molly cried so loudly that Danny heard her as soon as he arrived home.
“What happened, darling? Why are you crying?”
Molly told him about the prom. “I don’t have a date. I even asked some boys if one of them would at least dance with me during prom, but they refused and laughed. I don’t want to go to the prom, daddy! I want to be alone! Goodnight!”
Molly turned her back on Danny and pretended to sleep, tears soaking her pillow.
Danny couldn’t just leave his daughter in distress. The next day, he bought Molly a beautiful prom dress. And on prom day, Molly was in for a huge tear-jerking surprise. Her dad was taking her to prom.
Senior students and their parents were flocking outside the hall when a loud screeching roar of an engine drew their attention.
Danny jumped down from the truck. He put a wheelchair on the lawn and helped Molly get out. He pushed the wheelchair on the red carpet as the gathering watched in amazement.
Danny hit the dance floor with his daughter as the music rolled. He lifted Molly and carried her around in circles, syncing with the melodious musical night. For a moment, Molly forgot that she had a disability and laughed her heart out as her dad kept swaying her in his arms.
“My dad is my real superhero. I love him more than anything else in this world. I feel blessed and proud to say I’m his daughter,” Molly cried to her friends after the dance.
Meanwhile, Danny became the show stealer. All the parents flocked around him to praise and applaud him. Danny then shared a bit about himself and his daughter, knowing little about how that evening would soon change their lives.
Danny and Molly returned home, talking about the fun they had. Then Danny put Molly to sleep in her bedroom and silently crept out of the house.
It turned out Danny had been working a second job as a caregiver at a local nursing home. Besides his part-time day gig as a truck driver, he worked overtime to save money for his daughter’s treatment. When Molly’s disability was diagnosed years ago, many told Danny and Daisy that she would never be able to walk.
But one doctor had assured them he would treat the girl and restore her ability to walk. So Danny quit partying in pubs with his friends and started working two jobs.
Daisy had misunderstood him and thought he was wasting his time at the pub. Danny tried explaining to her, but she never trusted him. Her constant doubts and heated arguments led to their split shortly after. Danny never bothered because he was only focused on saving money for Molly’s surgery and worked hard for the next several years.
It pained Danny whenever he recalled his past. Even that night, while driving to work, he could not shake his thoughts off the terrible things his ex-wife told him. He finished his shift and returned home, unprepared for the surprise that awaited him and Molly.
That morning, when he returned home from work, Danny was in for a sweet surprise when he found a package in his mailbox.
“A parcel?? Who sent it?” he wondered. A card on it read: “Dad of the Year!”
Inside, Danny found a check for $10,000 and another note:
“Dear Danny, we hope this will improve your daughter’s life. Good luck with her surgery, and we hope you spend more time with her in the evenings. Best Wishes, Your Prom Buddies!”
Danny realized the parents he’d met the previous night were behind this. He shed tears of joy and shared the good news with Molly.
“Really?! My God, daddy…This is unbelievable!” She laughed and cried on his shoulders.
With the money Danny had saved and the $10,000 check, Molly got her surgery. It was successful, and gradually, she was able to walk without crutches.
Meanwhile, Danny quit his second job to spend more time with his daughter. She earned a scholarship to study architecture in another state and was set to leave in three months.
Danny wanted to make the best use of the available time he had with Molly. He taught her to cook, dance, cycle, and even run. He just wanted his daughter to live a normal life and never look back to the days when she was using a wheelchair and crutches.
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