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
In-Laws Kicked Us Out of the House They Gifted After We Paid for Renovations — Then It Got Even Worse
When Mike’s parents offer him and his family a home, they are over the moon. Mike and Maria have a growing family, and they need the extra space. So, they venture into renovations, making the house a home. But one day, Mike’s parents called, wanting their home back.
When my in-laws offered us a house, we thought it was a dream come true. With three kids and a tight budget, any help came as a blessing.
A close-up of a house | Source: Midjourney
But, let me be honest with you: the house was far from ideal.
“It’s in the middle of nowhere, Mike,” I told my husband when we were sitting on the couch talking about the possibility of moving into the house.
“It’s miles away from the kids’ school and our jobs! We’ll have to leave a lot earlier just to make it on time,” I said, sighing.
A couple sitting on a couch and talking | Source: Midjourney
“I know, Maria,” my husband said. “It irritates me to think that the nearest grocery store is about twenty minutes away. But I don’t want to be ungrateful.”
And I understood that. In fact, their gift had come at the perfect moment. We had outgrown our little two-bedroomed house. It was now cluttered, and our three kids had to share one bedroom.
A cluttered bedroom | Source: Midjourney
“We’ll do it for the kids,” I said, taking his hand. “Whatever happens, we’ll make it work for them.”
“Think of it as a fresh start, kids,” Mike’s mom said when we went over to their home for dinner. “You’ll love the peace and quiet, and the kids will have a lot of space to run about in. This is going to be good for you.”
“Yes, Mom,” Mike said. “We agree with you. We’re looking forward to this new start and just going on a journey together as a family.”
A family sitting at a table | Source: Midjourney
The house itself was a fixer-upper, to put it mildly. There was an entire to-do list of things that needed to be done. The house needed a new kitchen, the wiring needed to be updated, and the bathrooms needed an overhaul.
We knew it would be a big project, but at the end of the day, Mike and I wanted this house to be the home our children grew up in.
“The yard is so big, honey,” Mike told me. “Can you imagine all the birthday parties and even having our kids getting married from here? I love it.”
We poured all our savings into renovating it, making it not just livable but a true home for our family. Our children deserved it.
An outdoor birthday party set up | Source: Midjourney
As things were falling into place, Mike, the tech enthusiast, even set up a state-of-the-art smart home system.
“At least it’s ours,” Mike said, smiling as he showed me how the new system worked. “It finally feels like home.”
A few months went by, and we were settled into our new home. The children adapted beautifully, and Mike and I got closer as a couple. We went on long walks together, and the kids went on picnics together all the time.
Our family had grown closer together.
A picnic set up | Source: Midjourney
Then, last month, my in-laws dropped a bombshell. They decided to sell their current house and buy a lakeside cabin. To fund this new venture, they needed our house back.
What? How? This had become our home.
We were absolutely stunned. They insisted that although they had gifted it to us, they still had a right to take it back. The sense of betrayal was overwhelming.
“They can’t do this,” Mike fumed, pacing our newly renovated kitchen. “We have a letter from them saying it was a gift!”
A shocked couple | Source: Midjourney
My husband and I couldn’t believe it. We had a written letter from them, clearly stating that the house was a gift. We decided to fight back, hiring a lawyer to help us navigate this sudden crisis.
We provided all the documents, receipts, and the gift letter. We were convinced that there had to be some legal ground we could stand on.
“I don’t know what else to do,” Mike said one morning when we were having our coffee together. “I don’t know how we’re supposed to find another place and uproot the kids again. This isn’t fair!”
A stack of paper | Source: Midjourney
Weeks passed as we waited for a resolution. But I was just getting more agitated as the days went on. Mike told me not to do anything until the lawyer got back to us. But I couldn’t wait.
I couldn’t sit back and do nothing while we waited for our home to be taken away from us. So, I spent hours looking at rentals available in the area. I just needed to have options available on hand.
I didn’t know what was coming. And I couldn’t believe that Mike’s parents would willingly put us in this situation.
A woman using a phone | Source: Unsplash
But then, the lawyer did eventually get back to us.
He walked up our driveway expressionless, which immediately made me think that there was no good news coming.
“I’m afraid there’s not much we can do,” he said. “The property was never legally transferred into your names. The documents show them as the legal owners. So, I’m sorry, but Mike’s parents are the owners.”
A man in a suit walking | Source: Midjourney
The news was devastating.
I felt my entire stomach drop.
Mike, furious and heartbroken, suggested we undo all the renovations out of spite.
“They used us,” he said bitterly. “We should take back everything we put into this place.”
But I couldn’t bear the thought. Despite everything, we couldn’t stoop to that level.
“We’re better than that,” I said. “We’ll find another place and make it ours.”
An expressionless woman | Source: Midjourney
So, we packed our belongings and moved into a tiny apartment closer to the city.
It was cramped, but it felt like a fresh start, free from the manipulation of my in-laws.
The kids adjusted surprisingly well, finding new friends and enjoying the proximity to their school and activities.
“I feel like we failed our children,” I told Mike when we were unpacking our kitchen items. “I just hate that they have to share a room again. And bunk beds? You know they hate this!”
“I know, my love,” Mike said. “But it’s just for now. The moment we can move to something better, we will. I promise you.”
A small apartment | Source: Midjourney
Just when we thought that the drama was over, my in-laws reached out to us again. They were struggling with the smart home system Mike had set up.
“We can’t figure out how to use the lights, let alone the heating!” Mike’s dad complained over the phone. “Can’t you come back and help us out here?”
The irony wasn’t lost on us.
An elderly man using a phone | Source: Midjourney
We had made that house livable and even comfortable, pouring our money and energy into it. Now, they were reaping the benefits of our hard work, but they were clueless about managing the systems we installed.
Despite their pleas, there was no way that we were going back.
“No,” Mike said firmly. “The house wasn’t right for us. We’re staying where we are.”
A man holding his phone | Source: Midjourney
The trust was shattered, and the house, with all its tech features, was a constant reminder of the betrayal. Living in the cramped apartment wasn’t easy, but we found solace in the fact that we were free from emotional manipulation.
“This isn’t going to be forever, Maria,” Mike said. “I promise you. I’ll fix this.”
A couple embracing | Source: Midjourney
The experience left us wary of gifts that come with strings attached. We learned that sometimes, what seems like a generous gesture can be a way for others to control your life.
As for my in-laws, they eventually figured out the smart home system, but the damage was done. Our relationship with them has changed irrevocably.
“Please, come over for dinner,” Mike’s mother said. “We miss you guys, and we miss the kids terribly.”
An older woman using a phone | Source: Midjourney
“I’m sorry, Eileen,” I said. “But we’re just so hurt. And you should have known better. You’re a mother; you know how important it is for kids to have stability. And you and Derek took that away from us.”
“Calm down, please, Maria,” she said.
“No, because I don’t think you understand the extent of our wounds. Mike is so disappointed in you both.”
Without another word, Eileen cut the call.
“Oh, well,” I said to myself as I started chopping vegetables for dinner. Mike and the kids would be home soon.
A woman in the kitchen | Source: Midjourney
What would you have done?
If you enjoyed this story, here’s another one for you |
I Accidentally Found Out My Friend’s Husband Was Cheating – I Couldn’t Help but Take My Revenge
Allison decides to hold onto her youthful side as she drives a taxi during her spare time. But one day, her friend’s husband is her passenger. As she takes the man to his destination, he asks for a detour, revealing a side of him she didn’t know. Next, Allison has to decide whether to be good at her job and protect her friend or help show her the truth.
Driving a taxi at 65 years old wasn’t part of my retirement plan, but it became my passion. I had been a writer for a women’s column for the better part of my career, and since retirement dawned, I only wrote a few articles per month.
A person using a typewriter | Source: Midjourney
“Just something to keep the old clogs working,” my editor, Elena, said when I told her that retirement was knocking on my door. “You don’t have to commit to it, Allison. It can be a freelance role, if that’s what you’d like. But just write for us every so often.”
I agreed, what else did I have to do with my time anyway?
But then, the open road, the hum of the engine, and the stories of my passengers kept me going.
“Mom, why?” my son, Darren, asked me. “Like really? Driving people around?”
A smiling man | Source: Midjourney
“You’ll understand the need to do something freeing when you’re older, son,” I told him. “Let me do this while I still can. And what’s better than enjoying what I do?”
Yesterday was one of those days that I’ll never forget because it reminded me how foul people can be.
The previous day, one of my regulars, Jane, called me. She was a lively 55-year-old woman, and over the years, we had become friends.
A smiling older woman | Source: Midjourney
“Hi, Allison,” she said on the phone. “I need a favor.”
“If it involves those croquettes with the peas that you’re trying to get me to eat, it’s a hard pass,” I chuckled. “What do you need?”
“Mike is leaving on a trip tomorrow, and he needs a ride to the airport. I’m going to be babysitting the grandbaby, so I don’t want to disturb her routine.”
People at an airport | Source: Midjourney
Read the full story here.
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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