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 Parents Arranged a Marriage for Me, So I Decided to Test My Wealthy Fiancé
When Nadia returns home from college abroad, she has no choice but to agree to an arranged marriage to a wealthy man—a man chosen by her parents. But as the tentative date for their wedding draws closer, Nadia decides to test him, to truly understand who she’s marrying.
I never imagined that I’d find myself disguised as a homeless woman, sitting on a sidewalk outside of a restaurant. I sat there, hunched with a shawl wrapped around my shoulders.
A woman sitting on the floor | Source: Pexels
People passed me without paying any attention, as I watched for the sleek black car that often carried my fiancé, Danny.
Despite it being the 21st century, in my culture, arranged marriage still holds its own.
A black Mercedes-Benz | Source: Pexels
But I had been studying in America for the past four years, and my ideal of independence and personal freedom was something very different from what I had left home with.
Now, I found myself rebelling at every turn.
A woman in a red coat | Source: Pexels
When my parents first broke the news of my engagement to Danny, I was still ensconced in the States—my mind buzzing with new ideologies and lectures on autonomy.
“Now that you’ve been abroad and have studied,” my mother said, “it’s time for you to become a wife.”
I tried to protest, but it always fell on deaf ears.
A smiling woman in a white dress | Source: Pexels
“Nadia,” my mother said, “there is no choice here. Your father and I have done our research. Danny is a good one. He will take care of you.”
My mother moved around the kitchen, mixing a concoction of spices as she began to cook dinner.
Assorted cooking spices | Source: Pexels
“And that’s just it?” I asked, making some tea. “I have to marry this man?”
She nodded and smiled at me.
“Nadia, your father and I did it—we had an arranged marriage, and everything turned out well for us.”
A bride and groom holding hands | Source: Pexels
Now, I was faced with meeting a stranger whom I was going to marry—a stranger and his affluent family.
“You’re going to meet him soon, and his family. They own a line of restaurants, darling. They’re always going out of their way to help people.”
Restaurant interior | Source: Pexels
A few days later, we were all settled around the dining table. It was the first time that I was meeting Danny, and I had no idea what to expect.
When I stepped out of the house, he was there in the driveway, dressed in a suit—holding a gift bag and flowers.
A bouquet of roses | Source: Pexels
On first impression, he was good-looking, but I needed him to be more than just a nice face to look at.
This man was going to be my husband. I was stuck with him. And judging from the way my parents were behaving, I didn’t have a choice in the matter.
A man wearing a suit | Source: Pexels
As my father welcomed Danny and his parents into our home, my mother brought out a tray of tea and sweets.
“I didn’t know what you’d like,” she said, “so I got everything.”
Tea on a tray | Source: Unsplash
Danny smiled at her; he seemed to genuinely care about impressing my parents. We exchanged polite conversation during the tea, and when it was time for us to have dinner, we sat around the table.
“Danny,” my father said, pointing to the head of the table, “sit here.”
My mother began to fuss over Danny and his family, ensuring that she piled their plates high with food.
A table full of food | Source: Pexels
“I need you to leave here knowing that you’ve been fed,” she said.
I poured myself a glass of juice. It was going to be a long meal.
“Why did you decide to study in America?” Danny asked me, frowning over his glass of water. “Didn’t you want to stay around family?”
Juice in glass bottles | Source: Pexels
“I applied not thinking that I could get in,” I admitted. “But then I did, and I wanted it to be a new challenge for me.”
“But being away for so long?” he pressed. “I bet you spent time in the library.”
“It was just four years. I came home a few times anyway.”
A library | Source: Pexels
“Family is very important to me, Nadia,” he said firmly.
I looked at my mother, who refused to meet my eye. Without me replying to Danny, the silence took over for a few moments. Only the sound of scraping cutlery and chewing could be heard.
A woman eating | Source: Unsplash
“Tell Nadia about your charity,” my father said, beaming at me.
“Oh!” Danny’s mother exclaimed, quickly putting her fork down.
She went on at length about how Danny feeds homeless people all the time, and that he had scheduled a roster for different areas around us.
Bags of food | Source: Unsplash
“Nobody will go hungry if we can help it,” Danny’s mother said.
My goodness, I thought to myself as I dug into my chicken. Do I really need to bear this for the rest of my life?
The dinner ended, and my husband-to-be left the house.
A plate of food | Source: Unsplash
“Don’t you love him?” my mother asked as we washed up the dishes and cleaned the kitchen.
“I don’t know him, Mom,” I said.
“But you will,” she replied, drying the plates with a dish towel. “You will get to know him soon.”
A person washing a glass | Source: Pexels
I didn’t have the energy to deal with it further. I went to my bedroom and sat down, wondering how I could just give in to tradition after having been away and free for so long.
I yearned for my college dorm and the liberation that had come with it. But I also knew that I would have to let go of that.
A woman in her room | Source: Pexels
Instead, I had to wait for the day of my arranged marriage. As the months closed in, the wedding drew closer, and I began to get anxious—needing pills to sleep.
I didn’t know how I was going to marry Danny, knowing only the bare minimum about him.
One morning, while pouring myself some cereal, I decided that I would dress like a homeless person and wait outside the restaurant that Danny was based at. I needed to see how he would react to someone in need.
A bowl of cereal | Source: Pexels
As the car approached, I huddled into my disguise, my voice hoarse as Danny stepped out of the car.
“Excuse me, Sir,” I said. “Could you spare…”
Danny paused, his brows furrowing slightly.
“Ma’am, what do you need? I can’t just hand you money or food for the day. We need to help you long-term.”
A man frowning | Source: Pexels
My heart tightened.
“There’s a shelter not far from here,” he said. “I can take you there, my mother volunteers there, too. You’ll be safe there. You can get a meal, a shower, clean clothing, and we can talk about getting you on your feet.”
I stood up and pulled my shawl away, revealing myself to him.
“Nadia?” he exclaimed, his eyes wide. “What are you doing?”
A shocked man | Source: Pexels
“I was testing you, Danny,” I said. “I wanted to see if you really are the person they say you are. I just needed to know. How else can I marry you?”
Danny looked stunned, then a wry smile spread across his face.
“I guess I should be honest too, then. I’ve been horrible on purpose, hoping you’d call off the wedding.”
His candidness took me aback.
A smiling man | Source: Pexels
“Why would you do that?” I asked.
Danny sighed, running a hand through his hair as he silenced his ringing phone.
“Because I thought it was all a farce. I didn’t want to be part of an arrangement. Not really. I knew that it needed to be done, because of my age. But I’ve wanted love. I’ve wanted to marry for love.”
A man holding a phone | Source: Pexels
As we sat down on a nearby bench, Danny opened up about his past.
“The parents you met are my adopted parents. My mother died when I was very young, and they took me in. I’ve built my entire persona to help people who are where I once was. It’s not just philanthropy—it’s personal.”
His words echoed in the cold air—each syllable heavy with emotion.
“Yes, I am successful. But I never wanted to use that success as leverage for a marriage. I wanted someone to see me, not my money or my past.”
Flowers on a grave | Source: Pexels
We talked through the evening, unraveling the misunderstandings and the pressure from our families. It was the first time we truly connected, seeing each other beyond the expectations set upon us.
In the weeks that followed, we began dating—real dates, filled with genuine laughter and shared dreams. Our parents saw the change in us, the way we looked at each other with newfound respect and affection.
Soon, we’ll be married, but now, I’m content with the reality of it.
A couple holding hands | Source: Pexels
What would you have done?
If you enjoyed this story, here’s another one:
When Elle’s mother passes away, she moves through the funeral in a daze. But then, she stumbles upon a man who closely resembles her. When he approaches her, he reveals that he is her biological father—who had been hidden away all this time. Elle doesn’t know whether she should tell her father and risk losing the only other parent she has ever known.
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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