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
I Booked a $2,000 Rental for a Group Trip, but No One Paid Me Back Their Share of the Cost – They Didn’t Get Away with It
Excitement for their weekend getaway turned into frustration as Sarah’s friends dodged paying their share of the $2,000 cabin rental. Little did they know, she had a plan to make sure they didn’t get away with it.
Every year, my friends and I plan a girls’ weekend getaway. We take turns organizing, and this year, it was miy turn! I was excited to find the perfect spot: a cozy cabin nestled right on a sparkling lake.
We all squealed with delight when I sent the pictures.
A woman using her phone | Source: Pexels
The place looked like it came straight out of a magazine. It had a cozy cabin with a fireplace, stunning views of the lake, and even a hot tub.
The total cost was $2,000 for the three-night stay, which amounted to a very reasonable $250 each for our group of eight.
“Since I went ahead and booked the cabin, I covered the upfront cost,” I told my friends. “But to make things easier, I’d appreciate it if you could all pay me back before the trip. Does that work for everyone?”
A woman sitting in a living room | Source: Midjourney
“Sounds perfect, Sarah!” Mary chimed in first. “Thanks for taking care of that.”
“Absolutely, no problem at all,” echoed Ella.
“Great, that works for me too!” chimed in Brittany.
One by one, everyone around the table agreed.
“Yep, sounds good”
“No worries, I can do that.”
The confirmations rolled in. It seemed everyone was happy to handle their share and promised to pay me before the trip started.
Easy peasy, right?
Wrong.
Close-up of a woman’s face | Source: Midjourney
As the trip approached, the easy peasy turned into oh-so-frustrating.
First, it was Mary. “Hey Sarah,” she chirped, “my car needs new brakes, so I might be a little late on my payment. I’ll get it to you next week.”
A week later, it was Brittany’s turn. “Ugh, student loans are killing me this month. Can I hold off until next payday?”
“I just need to wait until my next paycheck,” Melissa told me.
Weeks went by, and as I reminded them to pay back, they came up with more excuses.
Close-up of a phone in a woman’s hands | Source: Pexels
Each excuse was new and none of them overlapped. It seemed like they were together in this.
Then came the radio silence. Nada. No texts, no calls, nothing from Ella, Dana, or even reliable old Lisa.
By the week before the trip, I was out $2,000 and feeling completely used.
The same people I called my “friends” had indirectly refused to pay me back. The people I trusted the most had suddenly decided to team up against me.
Why were they doing this?
A serious woman | Source: Midjourney
Had I done something wrong? Or was this an attempt to see how I would react to such a tricky situation? I didn’t know what it was, but it was making me super angry.
I knew I had to do something drastic, something that would make them understand I wasn’t a doormat.
As a result, I decided it was time to teach them a lesson they wouldn’t forget. Now, I’m not one for confrontation, but this was ridiculous.
The night before the trip, I took a deep breath and picked up my phone to execute the first step of my plan.
A woman using her phone | Source: Midjourney
I sent a group text, bubbling over with fake excitement. “Can’t wait to see you all at the cabin tomorrow! Gonna be the perfect weekend getaway!”
Little did they know, I had a devious plan brewing
The next morning, I woke up extra early and hopped out of my bed. Throwing on clothes, I raced out the door, eager to transform the cabin into our own little haven.
At the grocery store, I pushed my cart down the aisles.
A grocery cart filled with goods | Source: Pexels
A giddy smile appeared on my face as I filled it with fresh fruit, cheese, and enough snacks to satisfy an army. I even got the best selection of wine and juices. I wanted to make sure my friends were well-fed and taken care of.
After paying for the snacks and drinks, I got back into my car and drove towards the cabin. It was even more beautiful in person, the sunlight glinting off the lake like a million diamonds.
I stocked the fridge with everything that I had bought.
A woman putting something in the fridge | Source: Pexels
I even prepped a bonfire for that night, complete with cozy blankets and marshmallows.
The place looked perfect. I knew my friends would have the best time of their lives here.
But here’s the catch: I took the keys and the garage door opener with me when I left for an “errand.”
Before locking the cabin, I texted all my friends that I was out for an urgent task and would make it there by the time they arrived. They trusted me, just like I did when I asked them to pay me back.
However, they broke my trust, and so did I.
A woman holding a key | Source: Midjourney
If they wanted to have a good time in the cabin, they had to follow my rules. They had to earn their weekend getaway.
I wasn’t going to let them have a good time when all they did was ignore my texts and calls.
By lunchtime, my phone started blowing up. Frantic texts and calls poured in from my friends.
“Hey, Sarah, we’re here at the cabin, but the doors are locked!” Ella said.
“Did you forget something?” Mary asked.
A woman holding her phone | Source: Pexels
I kept my cool, replying with a simple, “Oh no! So sorry, guys. Must have left the keys at home. But hey, the good news is I’m on my way back now!”
Was I on my way back? No!
I was sitting at a nearby cafe, sipping on my favorite iced latte. I enjoyed reading their texts as they reached the cabin one after the other.
After I sent the last message, the frequency of their texts dropped. They felt relieved I was on my way back, but the truth was entirely different.
A woman in a coffee shop | Source: Midjourney
As their short-lived relief faded, they started calling and texting me again. This time, their messages were way more desperate. Some of my friends were angry, while others were struggling not to lose their temper.
“How can you be so forgetful, Sarah?” Lisa asked.
“I can’t believe you’re making us all wait like this!” Dana said. “I thought this was supposed to be a fun trip.”
Finally, I decided to drop the bomb.
A woman looking outside a window in a coffee shop | Source: Midjourney
I sent a calm message: “Look, I’ll be happy to come back and let you all in, but only once everyone has sent over their share of the rental cost.”
Silence.
Then, a flurry of activity.
Apparently, the prospect of a luxurious weekend getaway suddenly trumped car troubles, student loans, and all the other excuses they’d cooked up.
My phone buzzed with Venmo, PayPal, and Zelle notifications as payments started rolling in.
Within an hour, every penny was accounted for.
Close-up shot of a phone | Source: Pexels
“You guys could have done this before!” I said to myself before grabbing the keys and heading back to the cabin.
Their eyes lit up as soon as they saw my car. Some walked toward me, others to the door.
“Sarah! Finally!” Mary exclaimed, relief evident in her voice.
I stepped out of the car, keys in hand. “Oh, so now I’m ‘finally’ here? How convenient,” I said, my voice dripping with sarcasm.
The group fell silent, guilt spreading across their faces.
A serious woman | Source: Pexels
“Look, I’m sorry,” Brittany started. “But you have to understand, I really—”
I cut her off. “No, Brittany. You all made excuses. I trusted you, and you took advantage of that.”
Lisa stepped forward, trying to mediate. “Sarah, we messed up. But can’t we just put this behind us and enjoy the weekend?”
“Enjoy the weekend?” I scoffed. “After you all made me feel like a fool? After I had to practically blackmail you to get my money back?”
“We didn’t mean to hurt you,” Ella said softly. “We just didn’t realize—”
A woman speaking to her friend | Source: Midjourney
“Didn’t realize what? That $2,000 is a lot of money? That friendships are built on trust and respect?”
A tense silence fell over the group. For a moment, I thought confronting them was a bad idea. I thought they’d say they didn’t want to be there anymore.
I stood my ground despite the fear, letting the weight of my words sink in.
Finally, Mary broke the silence. She wrapped me in a giant hug.
“Sarah, I’m so sorry about the car thing. You were totally right to be mad.”
Brittany chimed in, “Yeah, me too. I’m sorry. We’re all sorry.”
A group of friends hugging | Source: Pexels
They all finally realized what they had done.
I took a deep breath, looking at each of them. “I’m glad you understand now. But remember, respect is a two-way street.”
We may not be planning any luxury cabin getaways anytime soon, but at least we’ll be doing it with a renewed sense of understanding and responsibility.
This whole experience definitely made for a memorable story, even if it wasn’t exactly the relaxing weekend I’d planned.
But hey, sometimes the best lessons come wrapped in a little frustration and a whole lot of determination.
What do you think?
A lakeside cabin | Source: Pexels
Here’s another story you might like: Eight hundred dollars plus. That’s what Jack’s “boys’ night out” bill came to, and he expected his wife, Lora, to foot it. Waitress Melanie, witnessing Lora’s despair, concocted a bold move to ensure Jack’s night didn’t end as he planned.
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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