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 Came Home with My Newborn Twins to Find the Locks Changed, My Stuff Thrown Out, and a Note Waiting for Me
After giving birth to my first children, I thought my husband would start choosing us more over his mother, but that wasn’t the case. This time, he’d chosen her side over me for the last time, so I exposed her for the bully and liar she was.
You’d think bringing home your newborn twins would be one of the happiest moments of your life. For me, it started like that, but it soon turned into an absolute nightmare!
An upset mother with her newborn babies | Source: Midjourney
After three days in the hospital, recovering from a grueling delivery, I was finally discharged and ready to head home with my beautiful twin daughters, Ella and Sophie. I’d imagined this moment for months: Derek, my husband, picking us up at the hospital with flowers, tears of joy in his eyes as he took one of the girls into his arms.
But instead, at the last minute, I got a hurried phone call that changed everything…
An upset woman on a call | Source: Midjourney
“Hey, baby,” my husband said, his voice clipped. “I am so sorry, but I can’t come pick you guys up as planned.”
“What?” I asked, adjusting the swaddle around Sophie. “Derek, I just had twins. What’s so important that you can’t—”
“It’s my mom,” he interrupted. “She’s in bad shape. Hectic chest pains. I need to pick her up and take her to that hospital close to her.”
His words hit me like a bucket of cold water. “What? Why didn’t you tell me earlier? Derek, I need you here.”
“I know,” he said, exasperated. “But this happened suddenly, and it’s serious. I’ll come to you as soon as I can.”
An anxious man on a call | Source: Midjourney
I gritted my teeth, fighting the urge to scream because of how disappointed and frustrated I felt, but I replied, “Fine. I’ll just get a taxi.”
“Thank you,” he mumbled before hanging up.
My husband’s mother lived in a different city, so the chances of him getting back that same day to get me and the babies were unrealistic. Knowing how obsessed Derek was with his mother, he wasn’t going to leave her by herself, hence the taxi.
An upset woman on a call | Source: Midjourney
As the line went dead, my heart sank. I wanted to believe Derek wasn’t being callous, just overwhelmed and a mama’s boy. Still, the disappointment stung. The same mother-in-law (MIL) who insisted we make a separate set of keys to our house so she could help me with the babies was now suddenly unwell.
I tried shaking it off as I bundled the girls into their car seats that their father had dropped off the previous day and got us into a cab.
A woman in a cab with her children | Source: Midjourney
When we pulled into the driveway, I froze. My suitcases, diaper bags, and even the crib mattress were scattered across the front lawn and by the doorstep! A knot formed in my stomach. I paid the driver and stepped out with the twins, glancing around nervously. Something was obviously very wrong…
A messy front yard | Source: Midjourney
I approached the front door, fumbling with my keys while absentmindedly calling out my husband’s name, even though I knew he couldn’t be home yet. The key wouldn’t turn. Confused, I tried again. Nothing. Then I saw it, a folded piece of paper taped to a suitcase.
Get out of here with your little moochers! I know everything. Derek.
My breath caught, and my heart stopped. My hands trembled as I read the note again and again, trying to make sense of it while hoping it was a hallucination. This couldn’t be happening. Not Derek…
A shocked woman reading a note | Source: Midjourney
Not the man who held my hand through every doctor’s appointment, who cried when we heard our daughters’ heartbeats for the first time. Then the worst part of that day began…
Wanting answers, I called him immediately. Straight to voicemail. Again. Voicemail. Panic set in as Sophie’s cries joined Ella’s. I rocked their car seats, forcing myself to think.
A stressed woman holding a phone | Source: Midjourney
“Mom,” I whispered. My hands shook as I dialed her number.
“Jenna?” Mom answered on the first ring. “What’s wrong? Are the twins okay?”
I choked out the words, barely able to hold it together. I hadn’t wanted to involve my mother due to her ailing condition, but I believed this was one of those dire moments.
“Derek… He changed the locks. He threw my stuff outside. Mom, he left this awful note.”
“WHAT?!” Her voice shot up. “Stay there. I’m coming.”
An upset older woman | Source: Midjourney
Minutes felt like hours before she arrived. Mom took one look at the mess and narrowed her eyes, fuming.
“This doesn’t make sense! Derek wouldn’t do this; he loves you and the girls!”
“That’s what I thought,” I said, rocking Ella to calm her cries. “But he’s not answering. And what does ‘I know everything’ even mean?” I asked showing her the offensive note.
“I am so sorry, my darling,” she said while hugging me close. “Let’s go to my place until we can get a hold of your husband, okay?”
An older woman hugging a younger one | Source: Midjourney
She helped me load the bags into her car and whisked us back to her place. After my mother and I dissected what had happened and repeatedly called Derek with no answer, my anxiety spiked. That night, I barely slept.
The next morning, I decided I needed answers. Leaving the twins with Mom, I drove back in her car to the house. The yard was empty, my belongings gone. I knocked on the door. No response. I walked around to the back, peering through the windows, and froze.
A shocked woman peaking through a window | Source: Midjourney
Derek’s mother, Lorraine, sat at the dining table, sipping tea! I banged on the door, and she looked up, startled, almost spilling her tea before she saw me and smirked.
“What are you doing here?” I demanded, banging on the door.
Lorraine rose leisurely and opened it just a crack. “Jenna. You’re not welcome here, didn’t you see the note?”
“Where’s Derek?” I snapped. “Why did he—”
“He’s at the hospital in my city,” she said smoothly. “Taking care of his sick mother.”
A nonchalant older woman standing by a door | Source: Midjourney
I stared at her, disbelief washing over me. “Sick? You’re standing right here!”
She shrugged, her lips curling into a malicious smile. “Maybe I’m feeling better. Miracles happen.”
“You lied to him, didn’t you? You faked being sick!”
Her smile widened. “And?”
My hands balled into fists. “Why? Why would you do this?”
She crossed her arms, her smugness growing.
A smug older woman | Source: Midjourney
“I told Derek from the start that our family needs a boy to carry on the name. But you? You gave us two girls. Useless,” she confessed unapologetically, finally speaking her truth after all these years I’ve been with her son.
Her words knocked the air out of me. I was too stunned to speak, and she took my silence as permission to keep going.
“I knew you’d ruin my son’s life, so I took matters into my own hands. The note was a bit much, but I needed you to believe he wanted you gone. I even ensured he couldn’t call you by taking his phone right out of his pocket when he wasn’t looking. You were supposed to take your things and get out of our lives, but here you are…”
An angry older woman | Source: Midjourney
I couldn’t breathe. This woman had orchestrated everything, lied to her son, and got him to take her to the hospital under false pretenses before sneaking away, locked me out of my home, and stole his phone all because she disapproved of my daughters!
“You threw us out over that?”
“Of course,” she said, unbothered. “I even bribed a nurse at the hospital to keep him there. And it worked, didn’t it?”
I felt sick. “You’re deranged!”
“Call me what you want,” she sneered. “I call it protecting my family. Besides, my Derek always takes my side and will see things my way as usual.”
An arrogant older woman | Source: Midjourney
Her words echoed in my mind as I drove to the hospital where my husband was still waiting. With every mile, my anger grew. How could she justify such cruelty? My hands gripped the wheel tightly, knuckles white with fury.
I knew my MIL was mean, but I didn’t think she was evil! She never approved of my relationship or marriage to her son, always believing Derek deserved someone wealthier and fancier, unlike me.
An upset woman driving | Source: Midjourney
When I reached the hospital, I found my husband pacing in the waiting room, his eyes shadowed with worry.
“Jenna!” he said, rushing toward me. “Where have you been? I don’t have my phone or know your number by heart, so I couldn’t call you!”
“Your mother took your phone,” I cut him off. “She faked her illness and locked me out of the house!”
He froze, confusion and anger flashing across his face. “What? That doesn’t make any sense.”
A man at a hospital | Source: Midjourney
“She set me up, wrote a fake note from you sending me away, and bribed a nurse to lie to you,” I said, my voice trembling. “Lorraine’s at our house, sipping tea like she’s the queen of the world!”
“Wait. What? Why would she…”
“Because our daughters aren’t boys,” I said bitterly.
The shock turned to rage on his face. Without saying a word, he grabbed his keys and stormed out, with me following close behind. When we got home, Lorraine was exactly where I’d left her, looking utterly unbothered.
An older woman having tea | Source: Midjourney
But her smugness vanished when she saw the determined look on Derek’s face.
“Mom,” he said, his voice cold and sharp. “What did you do? I thought you were in the hospital?”
She opened her mouth, likely to lie, but Derek cut her off. “Save it. I know everything.”
“Derek, I was just trying to—”
“You’ve done enough,” he snapped. “You made me abandon my wife and children for a fake emergency! Then you locked my wife, who just gave birth, and our newborn babies out of our home! On top of that, you cut our ability to communicate during such a crucial time by stealing my phone!”
An angry man shouting | Source: Midjourney
“Derek, darling… I just wanted to keep you safe. This isn’t how this was supposed to go,” my MIL replied pleadingly.
“Keep me safe from my wife and children? Who told you I wanted boys? What makes you think my girls aren’t good enough for me just because of their gender? That’s a problem you have, not me, and if you want sons, I suggest you go make them yourself!”
I stood with my mouth agape, having never seen Derek this angry! I won’t lie, a part of me was proud that he was proving himself worthy of me by defending my and the children’s honor. At that moment, I loved him more than ever before!
A happy woman | Source: Midjourney
“Pack your things and leave,” he demanded.
She gaped at him, tears forming. “You can’t mean that. I’m your mother!”
“And Jenna is my WIFE! Those are my daughters! If you can’t respect them, you’re not part of our lives!”
For once, Lorraine was speechless. She stormed upstairs to pack, slamming doors as she went. Derek turned to me, his eyes full of remorse.
“I’m so sorry, my love. I didn’t know.”
I let out a shaky breath, the tension easing just a little. “I just want us to move forward.”
A happy woman with her man | Source: Midjourney
Lorraine left that night. My husband apologized repeatedly, vowing to make things right. And he did. He changed the locks, blocked his mother’s number, and even reported the nurse who had taken the bribe!
It wasn’t easy, but for months we worked on rebuilding our life. One evening, as I rocked Ella and Sophie to sleep, I realized Lorraine had tried to destroy us but only managed to bring us closer together.
A happy couple with their twins | Source: Midjourney
Sadly, Jenna isn’t the only daughter-in-law who has had to face a difficult MIL. In the following story, Michelle’s MIL surprises her and her husband with a DNA test for their son thinking it would finally break them up. But things didn’t play out in her favor, the way she imagined.
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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