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
A Sales Assistant Told My Wife She Wasn’t ‘Pretty Enough’ to Work in Their Store — I Returned a Few Days Later for the Perfect Revenge
A store assistant dared to bring MY wife to tears by being mean. She did that all because my spouse sought employment at the establishment she worked at. After hearing my wife’s tale, I took action to redress the situation. What I did ensured that the assistant would think twice when addressing anyone else!
An emotional woman crying | Source: Pexels
This is an exciting tale about pure and sweet revenge! My name is Thomas, and Emma, my wife, has ALWAYS had an eye for fashion. Her wardrobe is a testament to her impeccable taste. Not that I am biased or showing off, but my Emma knows all there is to know about the latest trends!
I mean, most days, she’s the one who dresses me. No, not because I am sexist and think it’s her job, but because she LOVES doing that. And to be honest, I look FANTASTIC each time, so I’m NOT complaining!
A woman picking out clothes for a man | Source: Pexels
For years, my wife skirted around her true passion. She did all sorts of jobs. Like being a receptionist, and a nurse at one point (sadly short-lived), and even dabbled in art. But she still couldn’t find her place.
Recently, my beloved wife decided to turn her passion for fashion (see what I did there) into a career. She started actively searching for a job in retail. Her thinking was that it would fit perfectly with her interests.
A woman dressed up and posing in a store | Source: Pexels
When she got home all emotional one day, she told me the story of what happened. Emma explained that on that fateful day, she was at the shopping center in the afternoon. She then noticed a famous lingerie store with a “Now Hiring” poster on the window.
Excited, she revealed, “I immediately went inside to inquire! But boy, was I in for the shock of my life.” She shared how her excitement started dying down when she approached the sales assistant and tried to speak to her.
A store assistant sticking a “Now Hiring” sign | Source: Freepik
The rude woman didn’t even glance my wife’s way until she was DIRECTLY in front of her! A bit down but still quite enthusiastic, Emma asked about the job application process. Instead, the assistant looked her up and down with a sneer and an attitude. Then she delivered the stinging words:
“Look, hun, I don’t think you’re pretty enough for this job. NO CHANCE. Don’t even try, okay?”
A store assistant with an attitude | Source: Pexels
Before calming down enough to be able to tell me her story, my lovely wife was in tears when she came home. She was heartbroken by the cruel remark. I’ve never seen my wife so utterly devastated before, and my heart broke seeing her that way.
I wrapped my arms around her, trying to console her. “My love, don’t let her get to you. You’re beautiful and talented. You’re worth so much more than her words,” I said softly. “But why would she say that?” Emma sobbed. “I just wanted to apply for a job. I didn’t deserve that.”
A man comforting his crying wife | Source: Pexels
“She’s a small-minded person, my angel,” I tried consoling my wife. Seeing her so dejected made me FURIOUS! No one, and I mean NOBODY, should make my Emma feel this way, treat her that badly, and get away with it!
And you know what? As anger took over me, I figured it was high time someone showed that nasty assistant how wrong she was! I decided to give that sales assistant a lesson in humility she would NEVER forget!
A man contemplating something | Source: Pexels
Over the next couple of days, I concocted a plan. I reached out to my friend Mike, who works in the fashion industry, to get his help. Mike was more than willing to assist when he heard what had happened.
“That’s unbelievable, man. Of course, I’ll help. Let’s give her a taste of her own medicine,” Mike said over the phone. A few days later, my plan was set in motion. I dressed well, with the help of my Emma, and headed back to the lingerie store.
A happy man holding a beverage and talking on the phone | Source: Pexels
I had done my research enough to make sure the same sales assistant was working on that day. I then started pretending to browse the aisles, waiting for the perfect moment. When the store had only a few customers, I approached the assistant with a friendly smile.
“Hello, I’m looking to buy something special for my wife. Could you help me pick out a few things?” I asked. Her attitude changed immediately, seeing a potential big sale. She became attentive and started showing me various items.
A man browsing in a lingerie store | Source: Midjourney
“Absolutely, sir! We have a fantastic selection. What’s the occasion?” she asked, her tone now sweet as we went around the store. “Just a surprise for my wife. I want to get her something really special,” I replied, pretending to be thoughtful.
“Great! How about this piece? It’s one of our most popular items,” she suggested, holding up a delicate lace set. “Do you think this would look good on her?” I asked, examining the lingerie. “Oh, definitely! It’s one of our best sellers. Your wife will love it,” she assured me.
A store assistant working | Source: Pexels
“Can you show me a few more options? I want to make sure I get the perfect one,” I said, keeping her engaged. As she showed me more pieces, I made small talk to keep her invested. “So, how long have you been working here?” I inquired.
“About six months,” she replied. “It’s a great job if you have the right look for it.” I nodded, pretending to be interested. “That’s interesting. Do they hire often?”
“Only when they really need someone. They’re picky about who they bring on,” she said with a hint of pride.
A man talking to a store assistant | Source: Midjourney
After about thirty minutes, I told her I needed to step outside to call my wife for her opinion on one of the items. Instead of calling Emma, I called my friend Mike. He arrived quickly to enact his part of the plan.
We walked back into the store together. My pal approached the sales assistant and introduced himself. “Hi there,” Mike began, extending his hand. “I’m Mike Gladstone, a talent scout for a major fashion brand.”
A man reaching out to shake someone’s hand | Source: Freepik
He acted impressed with the store, hinting it was a great place to find fresh talent. “I’ve been looking for someone with a unique look and a great personality. Do you think you might have anyone like that here?”
The assistant’s eyes widened with excitement. “Oh, really? Well, I’ve been told I have a great look for this sort of thing,” she said, clearly thinking this was her big break. Mike gave her a critical once-over and shook his head.
A man contemplating something | Source: Freepik
“I’m sorry, but I don’t think you quite fit what we’re looking for,” he replied. “We need someone who STANDS OUT in the right way, you understand?” The assistant looked UTTERLY crushed!
Before she could respond, Mike turned to me. “What about you?” he asked, gesturing towards me. “You have an interesting look. Have you ever considered modeling?” The assistant’s jaw dropped! She was completely taken aback!
A shocked woman | Source: Freepik
I smiled and replied, “No, but I do have someone in mind who would be perfect for your campaign.” Without missing a beat, I said, “My wife, Emma. She’s stunning, confident, and absolutely beautiful inside and out.”
Mike nodded enthusiastically. “I’d LOVE to meet her. Let’s set up an interview.” I turned to the assistant, who was now pale and visibly shaken. Looking straight into her eyes to get the message across, I said:
“You know, it’s funny how perceptions can be so misleading. Maybe next time, YOU’LL think twice before judging someone based on their looks.”
A man talking to a female store assistant | Source: Midjourney
As we walked out, I could feel the assistant’s eyes burning into my back. Emma met with Mike later. Although she didn’t pursue modeling, the experience gave her a much-needed confidence boost.
“So, how did it go?” I asked my wife when she came back from her meeting with my friend. “It was AMAZING, actually! Mike was so kind and professional!” she beamed. “He said I had real potential,” she said, her face glowing with happiness.
A happy woman lying on a bed | Source: Pexels
“I told you, darling! You have everything it takes,” I replied, hugging her tightly. That evening, Emma and I sat down for dinner, reflecting on the events. “I can’t believe you did all that for me,” she said, holding my hand across the table.
“I’d do anything for you, my love. No one gets to make you feel less than you are,” I said firmly.
A happy couple talking | Source: Pexels
A week later, we were back at the shopping center. This time, Emma walked with newfound confidence. As we passed by the lingerie store, I couldn’t help but glance inside. The sales assistant was there, looking as if she was still recovering from the shock.
“Want to go in and browse?” I teased Emma. She laughed, shaking her head. “I’ve had enough of that store for a lifetime!” We continued walking, hand in hand, knowing that sometimes, the best revenge isn’t just a clever plan. It’s lifting up the ones you love and helping them see their true worth.
A happy couple having beverages at a shopping center | Source: Pexels
So, that’s my story. Sometimes, the best way to handle things is to make someone realize how wrong they were in the most public and humiliating way possible. And trust me, seeing the look on that sales assistant’s face was something I’ll remember forever!
Two men pleased with themselves | Source: Freepik
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