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 Fiancée Vacuumed Up and Threw Away My Dead Mother’s Ashes from the Urn
I treasured my mother’s ashes for three years after her death. Her urn was that one sacred thing I asked my fiancée to never touch. But in her rush to make our home spotless, my fiancée vacuumed up the ashes, threw them out with the trash, and hid the truth from me.
Does the death of a loved one mean they’re gone from us forever? My mother Rosemary was my sun, moon, stars, and everything in between. After her death, I still felt her presence through the urn that held her ashes. Until the day my fiancée decided to “clean” our apartment, and my world shattered all over again.
An older lady’s framed photo, an urn, and glowing candles on a table | Source: Midjourney
The evening air was thick with memories as I stood in our living room, touching the silver frame that held Mom’s favorite photo.
She wore her favorite white dress and smiled at the camera, her eyes crinkling at the corners.
It had been five days since the accident that killed Mom, but some days, the pain felt as fresh as the morning I got the call from the hospital.
A man holding an older woman’s framed photo | Source: Midjourney
“Hey, Christian,” my sister Florence called from the couch. She had moved in after Mom passed, and her presence helped fill the echoing emptiness of my heart.
“Remember how Mom would always say grace before dinner, even if we were just having cereal?”
I smiled, running my finger along the frame. “Yeah, and remember how she’d catch us sneaking cookies before dinner? She’d try to look stern but end up laughing instead.”
A sad woman looking at someone | Source: Midjourney
“God, the way she’d put her hands on her hips,” Florence said, wiping her eyes. “Like she was trying so hard to be mad at us.”
“‘Lord give me strength!’” we said in unison, mimicking Mom’s exasperated tone, and for a moment, it felt like she was there with us.
The front door opened, and my girlfriend Kiara walked in, her footsteps hesitant. She’d been like that since Mom died, always hovering at the edges of our grief, never quite knowing how to step in.
A woman in the hallway | Source: Midjourney
“I picked up dinner,” she said, holding up a takeout bag. “Chinese. From that place you like, Christian.”
“Thanks,” I replied coldly. Something had changed between us since Mom’s death. It was like a wall had grown where there used to be an open door.
Two weeks after the funeral, I came home early from work to find Kiara packing a suitcase. The sight stopped me cold in the doorway.
“Where are you going?” I asked, though the answer was written in every careful fold of clothing she placed in the bag.
A woman packing her clothes | Source: Pexels
She didn’t look up. “I need some time, Christian. This… all of this… it’s too much.”
“Too much? My mother died, Kiara. What did you expect?”
“I don’t know how to help you!” She finally met my eyes, her own filled with tears. “You cry every night. You spend hours staring at her pictures. You and Florence keep talking about memories I wasn’t part of, and I feel like an outsider in my own home.”
“So your solution is to leave? When I need you most?”
A sad man looking at someone | Source: Midjourney
“Please try to understand—”
“Understand what? That my girlfriend of four years can’t handle a few weeks of grief? That you’d rather run away than support me?”
“That’s not fair!” Kiara’s hands trembled as she folded another shirt. “I’m trying my best! But it looks like you’ll take forever to move on, Chris.”
“Your best?” I grabbed the shirt from her hands. “Your best is packing your bags while I’m at work? Not even having the decency to tell me to my face that you care more about yourself than me… and my grief?”
A shocked woman | Source: Midjourney
“I was going to call you—”
“Oh, that makes it so much better!” I threw the shirt across the room. “What happened to ‘I’ll always be there for you’? What happened to ‘we’re in this together’?”
“I’m not equipped for this, Christian. I can’t be what you need right now.”
“I never asked you to be anything but present, Kiara. Just to sit with me, to hold my hand, to let me know I’m not alone. But I guess that’s too much to ask, isn’t it?”
A distressed man with a woman | Source: Pexels
She picked up her suitcase, her shoulders shaking. “I’m staying with my friend Shannon for a while. I’ll text you. I just… I need space to figure this out.”
“Figure what out? How to be a decent human being? Go ahead, run away. It’s what you’re good at, isn’t it?”
Kiara left without saying anything.
Florence moved in the next day, bringing with her the comfort of shared grief and understanding. We spent evenings looking through old photo albums, crying together, and laughing at memories of Mom’s terrible dancing and amazing cooking.
A man watching a woman leave with her bag | Source: Pexels
“She would have hated this,” Florence said one night, gesturing at the takeout containers littering our coffee table. “Remember how she used to say fast food was ‘the devil’s cooking’?”
“But she’d still take us to McDonald’s after doctor appointments,” I added, smiling at the memory. “Said it was ‘medicinal French fries.’”
“Chris, did Kiara call?”
“Nope! Just texted. You know, I stayed with her through her father’s illness, her bad days, her everything. And yet here I am, alone in my own grief. I needed her, but maybe she just didn’t love me enough.”
An upset an sitting on the couch | Source: Pexels
The only way Kiara contacted me was through texts like, “Hope you’re okay.”
I typed and deleted, “I needed you, Kiara.” But sent, “I’m managing. Thanks.”
A month after Kiara left, she asked to meet at our usual coffee shop. She sat across from me, looking smaller somehow, her hands wrapped around an untouched latte.
“Shannon’s boyfriend confronted me yesterday,” she hesitantly began. “Called me selfish and cold-hearted. Said I abandoned you when you needed me most.”
A woman in a coffee shop | Source: Unsplash
I stayed silent, watching her struggle with the words.
“He was right,” Kiara continued. “I’ve started therapy, Christian. I want to be better. I want to learn how to be there for you, even when it’s hard. Especially when it’s hard.”
“How do I know you won’t leave again?” I asked, the fear raw in my voice.
“Because I love you,” she replied, reaching across the table. “And I’m learning that love means staying, even when it hurts. Even when you don’t know what to say or do. I’m sorry for being a jerk.”
A woman holding a man’s hand | Source: Unsplash
Life settled into a new pattern after that. Kiara moved back in, and three years later, we started planning our wedding.
Mom’s urn remained on its special table in the corner, surrounded by her photos and her plastic rosary — the one she’d carried everywhere, even to the grocery store.
“We should divide the ashes,” I suggested to Florence one evening. “You could have half.”
She shook her head, touching the urn gently. “No, let’s keep them together. It’s what Mom would have wanted.”
An urn on a shelf | Source: Midjourney
I nodded, tears welling up in my eyes as I thought about Mom and how much I’d miss her at my wedding. I’d already decided: the urn with her ashes would have a special spot in the front row of the church. It would make me feel like Mom was there, blessing me as I took this important step in my life.
The wedding planning consumed our days. And Kiara seemed different. She was more present and understanding.
She held me when the grief hit unexpectedly, sat through stories about Mom without fidgeting, and even asked questions about her sometimes.
Grayscale shot of bridal accessories | Source: Pexels
Then, the call from Florence came on a Tuesday evening, just three days before my wedding. “Hey, Chris? I was wondering if I could have Mom’s rosary. The plastic one? I found a photo of her holding it, and—”
“Of course,” I said, moving toward the urn. “Let me just—”
The words died in my throat as I opened it. Inside, where Mom’s ashes should have been, sat a Ziploc bag filled with… SAND? The rosary lay beside it, exactly where I’d left it three years ago.
The front door opened, and Kiara walked in carrying shopping bags. One look at my face, and hers drained of color.
“What did you do to Mom’s ashes?” I asked.
A man pointing a finger | Source: Pexels
She set the bags down slowly, her hands trembling. “Honey, it’s not what you think. I didn’t do it intentionally—”
“What did you do, Kiara?”
A long silence followed. Then she confessed, “I was cleaning while you were at work a few months ago. The apartment needed a deep clean, and—”
“And what?”
“I picked up the urn to clean the table and accidentally dropped it. It shattered. I quickly assembled the ashes into a bag. But the bag tore. The ashes spilled onto the carpet. I… I panicked. I vacuumed them up and threw the ashes into the trash outside.”
My knees buckled. “You vacuumed my mother’s ashes and threw them in the trash?”
A woman using a vacuum cleaner | Source: Pexels
“I didn’t know what to do. I got some sand from the park nearby. Found a replica of the same urn in the antique shop downtown. I filled it up with the sand. I… I thought you’d never open it again.”
“Never open it? You thought I’d never want to see my mother’s ashes again?”
“I was trying to clean the house. It was just an accident.”
“Clean?” I slammed my hand against the wall. “Those weren’t dust bunnies under the couch, Kiara! That was my mother! The only physical piece of her I had left!”
A shocked man | Source: Midjourney
“I’m sorry, Christian!” she sobbed. “I wasn’t thinking!”
“Clearly!” I picked up the urn, cradling it to my chest. “You weren’t thinking when you decided to ‘clean’ around the one thing I specifically asked you never to touch. You weren’t thinking when you vacuumed up my mother’s remains like they were dirt. And you certainly weren’t thinking when you replaced them with sand and lied to my face for months!”
“Please, Christian, we can fix this—”
“Fix this? How exactly do you propose we fix this, Kiara? Should we go dumpster diving? Should we sift through garbage bags looking for my mother’s ashes?”
An emotional, teary-eyed woman | Source: Midjourney
“I’ll do anything—”
“Did you even try, Kiara? Did you even attempt to salvage anything? Or did you just panic and run to the park for sand, like you always run away when things get hard?”
Her silence filled the room like poison.
“That’s what I thought.” I started gathering Mom’s photos from the table before dumping the sand from the urn. “You know what the worst part is? I actually believed you’d changed. I thought all that therapy and all those promises meant something. But you’re still the same person who left me when my mother died. You’re still running from the hard stuff.”
Close-up shot of an angry man yelling at a woman | Source: Pexels
“Our wedding’s in three days. Please… I’m sorry. Don’t leave me. Where are you going, Christian?”
“Away from you!” I grabbed my keys and things. “I can’t even look at you right now.”
Before stepping out, I looked back, hoping stupidly for a sign of regret. Anything to show she understood what she’d done.
But Kiara just stared at the floor, her face unreadable, and already distant. My chest tightened, and the last bit of hope drained out of me. Without another word, I turned and left, the empty urn heavy in my hands.
A man walking away with a suitcase | Source: Pexels
The hotel room I checked in felt sterile and cold. I sat on the edge of the bed, Mom’s photos spread around me. My phone buzzed continuously with messages from Kiara, but I couldn’t bring myself to read them.
How would I tell Florence? How could I explain that the last piece of our mother was likely buried in a landfill or blown away like dust because my fiancée treated her remains like dirt?
As dawn broke, I stared at the urn one last time, realizing I was left with only emptiness and betrayal.
A distressed man | Source: Pexels
Things would never be the same, and I didn’t know if I’d ever be able to forgive my fiancée. Maybe I didn’t want to. Maybe I never could. But deep down, in a corner of my heart, I hoped my mother would forgive me.
I took the rosary, feeling the familiar smooth plastic under my fingers.
“The night before your accident, you made Florence and me promise to keep it safe, Mom. Said it would help us find our way when we felt lost,” I whispered, tears brimming in my eyes.
“Maybe that’s why you wanted us to have it. Because you knew that someday, we’d need something more than your ashes to hold onto.”
A man holding a rosary | Source: Pixabay
I clutched the rosary tighter, remembering Mom’s words, “Love isn’t in the things we keep, dear. It’s in the memories we make and the forgiveness we offer.”
I don’t know if I can forgive Kiara. Every time I close my eyes, I see Mom’s ashes being sucked away into nothing. How do you forgive something like that?
I stepped out onto the seashore nearby. The city lights blurred through my tears as I clutched the empty urn and rosary to my chest. A gentle breeze stirred, reminding me of how Mom used to say the wind carried whispers from heaven.
An emotional man’s eyes | Source: Unsplash
“I’m sorry, Mom,” I said, looking up at the sky. “I’m so sorry I couldn’t protect your ashes. I had one job — to keep you safe. But I failed. But I want you to know… wherever you are… that you’re still here with me. In every breath I take, in every memory I hold, and in every prayer these beads have witnessed. I love you, Mom. I’ll love you until my last breath and beyond that. Please forgive me.”
The wind seemed to wrap around me like one of her warm embraces, and for a moment, I could almost hear her whisper, “There’s nothing to forgive, dear. Nothing at all. Love you too.”
Silhouette of a man standing on the seashore | Source: Pexels
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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