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
Woman Told Her Daughter Her Father Had Died – Years Later, the Girl Discovered a Heartbreaking Truth
When Cassie returns from a getaway with her husband and son, she walks into her home to see a cryptic message from her mother — telling her to watch a video. As Cassie presses play, her entire life changes. In the end, she’s left wondering which of her parents are worthy of forgiveness.
In my eyes, my father could do no wrong. He was everything I needed him to be and more. He was a businessman who was always traveling, but he ensured that he made enough time for me.
“You’re my little girl, Cassie,” he would say, bopping my nose with his index finger. “You’re the most special.”
A father carrying his daughter | Source: Pexels
My parents always went out of their way for me — ensuring that despite their busy schedules, we would have family dinner almost every night.
It was the one thing that kept me grounded while both of my friends from school were in the middle of their parents’ messy divorces.
“I think it’s trendy now,” I told my mother as she cut slices of banana bread for me after school one day.
Sliced banana bread | Source: Unsplash
“Cas, you cannot think that divorce is trendy,” she laughed. “It’s devastating and traumatic, and very few families actually keep things civil.”
“I’m just saying that it’s trendy because a lot of kids live between two homes,” I explained to her. “It’s one of those things we were talking about in class today.”
I was fourteen, and the world seemed more dramatic than it should have been.
A smiling girl in a hoodie | Source: Pexels
But what I didn’t know was that my words seemed to be an incantation that settled over our home.
A few weeks after that conversation, my father went away on a business trip. A few hours after he had been gone, there was news of his passing.
“How?” I asked. “How did he die?”
“I don’t know what to tell you, Cassie,” she replied. “I’m just saying what the paramedics told me.”
Two paramedics standing | Source: Pexels
“So what will we do next?” I asked.
“What do you mean?” she asked, puzzled by the question.
“For the funeral?” I asked. “Aren’t we going to have one?”
“I don’t think so,” my mother replied. “Dad wanted to be cremated and have his ashes spread at the beach. Let’s do that instead.”
A black and white urn | Source: Pexels
I couldn’t fathom why my mother would want to do that — but at the end of the day, she knew my father best. And the longer I thought about it, the more beautiful and sentimental a private ceremony at the beach felt.
“Don’t be difficult, Cassie,” my mother said when she saw me thinking about my next move.
“I’m not,” I said. “Really. I was just thinking about it. It’s a great idea, Mom.”
A pathway to the beach | Source: Unsplash
I could have fought her for a send-off that I thought would have been more appropriate. But what use would it have been? At the end of the day, we had both lost him.
The months following the beach ceremony felt weighted, and I knew that I was becoming deeply depressed — my father had been our world. And his absence was felt more than anything.
But, with time, I learned to live with it.
A girl sitting on the floor and looking out the window | Source: Pexels
Last week, I decided to book a cabin in the woods for a little family vacation. My son was adamant that camping was the new best thing, and I knew that despite the wonders of nature, I wasn’t going to camp in a tent without a bathroom in sight.
Instead, I thought that a cabin would be the best option — my husband, Derek, could camp outside with Drew, our son, if he insisted on it.
A cabin in the woods | Source: Unsplash
We had a dog, therefore, I asked my mother to house-sit for the week so that we could be at peace, knowing that Romeo was taken care of.
A week away was more than enough to restore my mind — and eventually, when we went back home, I was surprised to see that my mother wasn’t there. In fact, it looked like she had never been there.
A dog lying on the grass | Source: Unsplash
But there, on the coffee table, was a note beneath the TV remote.
Watch this, Cassie. I’m sorry. — Mom
I didn’t know what was in store for me, but while Derek got Drew into the bath, I put the TV on and began to watch whatever my mother had planned.
The TV flickered to life, and there he was, my father, his voice a long-lost melody, his image aged but still, unmistakably him.
A person holding a TV remote | Source: Unsplash
Tears streamed down my face as the realization that he was still alive enveloped me in a mix of joy and disbelief.
The video message was nothing short of unpredictable.
My dear Cassie, I’m still here, alive. I’m so sorry for the pain that you must have felt from my loss. But it was needed. I needed to be removed from your life because of the sordid truth of my past. Your mother knows everything, please ask her for the truth.
My health is on a steady decline, and I would love to see you and explain it all.
Love you, Dad.
An old man | Source: Pexels
Without telling Derek or Drew anything, I grabbed the car keys and ran out. I needed my mother to explain.
“So, I bet you’ve got questions for me,” she said, opening the door.
“Explain it all,” I said.
“Cassie, it’s heavy. You look tired from your trip; are you sure you want to do this now?” she asked.
I nodded. It was now or never. I needed to know why my father faked his own death to get out of our lives.
My mother made us some tea and took out some shortbread.
Shortbread cookies on a plate | Source: Unsplash
“Darling,” she said. “I’ll understand if you don’t forgive me, but there’s so much about that time that I need to tell you.”
I sipped my tea, trying to figure out what my mother was about to tell me.
“I remember that you were telling me about your friend’s parents getting divorced. Do you remember that?” she asked.
I nodded. Of course, I did. It was the strangest thing, but it was so common when I was in school.
“Well, your father and I were not legally married. So when I told him about our conversation regarding divorce, he was actually relieved. Without being married, there would be no divorce.”
A marriage certificate | Source: Unsplash
“What’s the big deal?” I asked.
“Then I found out that the real reason that we didn’t get married was because your father was already married to another woman.”
“What?” I exclaimed, almost dropping my cup. “To who?”
“To a woman in the town where he always had his business trips.”
“You didn’t know?” I asked, unable to believe her words.
A couple showing off their wedding rings | Source: Unsplash
“Of course not!” she exclaimed. “But when I pressed him about it, he decided to choose that family over us. So, I told him that the story was going to be his death.”
We were both silent for a moment.
Turns out that my mother told him that she would never tell me the truth, not when he was my favorite person. She couldn’t burst my bubble in that way. And she refused to let him see me one more time.
“It was better for you to think that it was an accident,” my mother said. “It just made more sense.”
Now, I understood why we didn’t have a funeral for him.
“What did we throw into the sea, then?” I asked.
“Dust,” she replied with a straight face.
A cloud of dust | Source: Unsplash
My mother had spoken to him twice over the years. The second time being a day ago.
During their meeting, my father confessed his imminent death due to illness and requested that she give me the recording. My mother, torn by guilt and love, chose to write me the note and have the recording all set for me to watch.
“I would have taken the secret to my grave,” she said. “But knowing that he was ill and wanted to see you just struck something in me.”
A cemetery | Source: Pexels
Compelled by a need to confront the reality of my father’s existence, I traveled to the state where he lived with his other family.
I spent a few weeks with my father — going in and out of hospitals, watching him take an array of different medication, and growing weaker by the day.
Sitting at his bedside, I listened to his stories, the regrets, the moments of joy, and the love he had for all his children — myself included.
When things started to go downhill, I asked Derek to fly over with Drew. It was going to be a fleeting moment, but at least I’d know that my son had met my father.
A sick old man | Source: Pexels
A few days later, my father died.
Even now, I don’t know if I’ve forgiven him for the lie of having a double life. I just know that when it came to it in the end — I wanted to spend time with him. I had shoved my feelings aside, hoping for memories that I could figure out later.
But now that the dust has settled, I’m trying to figure out if I should forgive my mother for lying.
Flowers on a grave | Source: Pexels
What would you do?
This work is inspired by real events and people, but it has been fictionalized for creative purposes. Names, characters, and details have been changed to protect privacy and enhance the narrative. Any resemblance to actual persons, living or dead, or actual events is purely coincidental and not intended by the author.
The author and publisher make no claims to the accuracy of events or the portrayal of characters and are not liable for any misinterpretation. This story is provided “as is,” and any opinions expressed are those of the characters and do not reflect the views of the author or publisher.
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