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
Felix put his head in his hands and sighed. No matter how often he went through the monthly figures for his home handyman business, he couldn’t deny the facts. He was facing another shortfall this month
Felix notices his elderly neighbor laboring to trim her overgrown yard and runs to assist. As a thank you, she thrusts an odd antique box upon him; however, Felix finds himself in serious legal hot water when her attorney calls to demand an immediate appointment.
Felix was looking over his handyman business’s monthly accounts when he heard a lawnmower snarl. When he peered out his kitchen window, he was startled to see an old woman named Mrs. McAllister using her cane as a walking aid and straining to maneuver her lawnmower with one hand.
Mrs. McAllister was crimson in the face and drenched in sweat when Felix caught up to her. She turned off the lawnmower.
“Felix…Can I help with something, please?you with? She gasped.
“Please move aside so I can assist you! To be honest, Mrs. McAllister, your son ought to be assisting you with these household tasks. It’s wrong to leave your aging mother to struggle on her own.
Felix was invited inside for a drink of lemonade by Mrs. McAllister after a tiring morning spent mowing and raking the tall, wet grass. The dirty mess of cobwebs, dirt, and trinkets in her house astounded him. Felix thought that his generous neighbor was no longer able to care for herself.
“You go now, sweetie.” On the table, Mrs. McAllister set down a glass of lemonade.
“I also want this to belong to you. This antique has been handed down through my family.
Felix scowled at the metal container she extended for him. It was quite weighty and featured a curious set of dials on the lid.
“Mrs. McAllister, I don’t need a fancy gift for such a simple task.” Felix returned the box to her hand.
Mrs. McAllister cast a disappointed glance. She demanded he take something to make up for his worries and went to get his daughter Suzie an apple-filled grocery bag. She then groaned loudly and collapsed into her armchair, obviously tired.
Felix left Mrs. McAllister to rest, insisting that she phone him the next time she needs assistance. Later on in the day, Suzie hurried up to Felix, grinning with excitement.
“Look, Dad! I found something under the apples that Mrs. McAllister gave us!” She pointed out to him the same weird metal box. “I can’t open it, but I think these dials are a combination lock.”
“Suzie, I know you adore vintage puzzle boxes and stuff, but we’re not keeping this.” He extended his hand to grasp the package. “I will give it back to Mrs. McAllister.”
Felix insisted even though Suzie was furiously unhappy. With the box in hand, he marched back to Mrs. McAllister’s house, but she did not answer the door. He groaned in frustration and reached for the door handle. He stepped inside after shouting to Mrs. McAllister that he was returning her box safely.
The body of Mrs. McAllister was hunched over in the recliner. Her eyes were empty and unseen as they gazed at the wall.
“Mrs. McAllister!” Felix hurried to her side and yelled, but it was too late—Mrs. McAllister had vanished.
It wasn’t until much later that Felix noticed the box was in his pocket. He looked for comparable antique boxes on the internet on a whim. When he eventually located a match, he cursed.
This was a $250,000 box!
Felix couldn’t return the package even though he hadn’t wanted to, and Suzie’s future would be guaranteed by that sum of money. For the benefit of Suzie, he had to sell it. Felix put the box somewhere safe in the interim. Felix received an odd phone call a few days later.
“This is Tim, the attorney for Mrs. McAllister. I would like to schedule a meeting with you right away. Are you free right now?
Felix was cautious about Tim’s haste, but he agreed to meet the lawyer at a town cafe. He was interested as to why Tim wanted to see him, despite his discomfort. When he came and found Henry, the son of Mrs. McAllister, sitting at a table with the man who had to be Tim, his uncertainty only deepened.
Felix joined them, and Henry sent him a look. Felix, allow me to get right to the point. A priceless heirloom—a tiny box with few dials on the lid—has vanished from my mother’s home. Since you were the last person in her home, I wanted to give you an opportunity to act morally.
“You believe I took something from your mom?” Felix bellowed. “Mrs. McAllister gave me the box as a token of appreciation for mowing her lawn—a duty you ought to have performed for her!”
“You would never have gotten that box from Mom!” Felix was stabbed by Henry with his finger. It was commissioned from a renowned artisan by my great-great-grandfather, a well-known politician! There are just two in the entire globe! I’ll give you $1,000 for the box if you return it to me. Alright?
“No.” Felix got to his feet. “When I put it up for auction, you are welcome to participate in the bidding. Henry, good bye.
Felix took the box to a nearby auction house the following day to have it valued. Mr. Whitaker, a serious guy with a snobbish accent, summoned him to an assessment in a back room. Ellen, a woman, also joined them.
Mr. Whitaker stated, “I can confirm right away that the craftsman’s mark on the underside is genuine.” That implies, sir, that this is a really noteworthy piece. One of just two worldwide.
Ellen bent to look inside the box. That is really beautiful.Could you please show me your provenance paperwork?
“Pardon me?” Felix queried.
A muscle in the woman’s cheek quivered. “Any verifiable document that demonstrates the authenticity of the artifact and your ownership, or a certificate of authentication, must be provided.”
Felix lied, saying, “Uh…I left all that stuff at home.” He objected to the direction this appraisal had gone. After removing the package from the table, he made his way toward the door. “I’ll go get it and come back right away.”
“You cannot be allowed to do that.” Ellen moved to the side, obstructing his way to the door.
“We have a duty to report any…discrepancies involving objects associated with historical personalities to the relevant authorities.”
Felix went into a panic. He swerved to avoid the woman and Mr. Whitaker, then shot out into the corridor. As soon as he arrived at the reception area, an alarm went off.
Felix ducked and slid past guards who were scrambling to stop him, feeling as though he was back on his high school football field. He sprang away from the grip of one and bolted out of the building onto the street. From then, he ran until his legs were completely numb.
Felix walked his living room, considering what to do. In order to put money into Suzie’s future, he had to sell the box, but he needed some sort of paperwork to make it happen.
He wished he could find out from Mrs. McAllister. She would likely be able to supply the precise documentation he required to show provenance as well as know exactly what they were. Felix thought for a moment, thinking there might be a market for the box. He didn’t want to do it, but he was stuck with no other option.
Felix went through his toolboxes and picked out a few necessary items, then went to the garage to get his boltcutter. Felix broke into Mrs. McAllister’s residence after Suzie went to bed that evening in order to find the documents he need.
Felix felt a shiver run down his spine as he entered Mrs. McAllister’s bedroom. The smell in here was still hers. He forced himself to see into her personal space even though it felt intrusive and spooky. The light in the bedroom came on while he was halfway across the space.
“You’re not so mighty and high now, Felix?” Henry snarled from the entrance.
Felix pivoted. Felix had a flash in his eyes as Henry snapped pictures of him with his phone raised.
Felix covered his face with a raised hand. Henry, this isn’t how it looks. All I need is—
“I know the paperwork for the box.” Henry grinned. “The auction house contacted me after you attempted to swindle them since my family is known to have a link to that box. I told them, of course, that you took it.
“That is untrue!”
“But without the right paperwork, it’s impossible to prove ownership.” Henry filled the entryway with his stance, arms crossed. “Neither can you sell it. I’ll give you till tomorrow at eight in the morning to turn it in; if not, I’ll phone the police.
Felix took out running from Mrs. McAllister’s house as Henry moved aside. He was burdened by the implications he now had to face. The day he discovered Mrs. McAllister dead, he wished he had left the box at her home.
However, she had desired it for him! Felix didn’t think Henry would follow through on his promise to turn over the box. Ideas were flying through his head. He knew what he had to do by daylight.
He woke Suzie and instructed her to hurriedly pack her bags, then requested his mom to come over right now. They were all gathered at the front door a few hours later. Now that he had covered everything, it was time to say their goodbyes.
Felix handed Suzie the box. “As soon as you can, sell it. Please don’t accept anything less than $100,000 for it. The only way to escape this disaster and yet make sure you have the best possible life is to do this.
Tightly hugging his daughter, Felix fought back the tears that threatened to well up in his eyes. One of the toughest things he had ever had to do in his life was say goodbye to her.
“Suzie, I know you’ll have a wonderful life,” he added, gazing into her eyes. “Travel to see what the world has to offer and study hard so you can make something of yourself.” Observe your grandmother.Family is vital, and we should show respect for the elderly.
In the distance, police sirens sounded. Half an hour had passed since Henry’s deadline at 8:30 a.m. He had a suspicion that those sirens were pursuing him. He kept his eyes on Mom and Suzie as they pulled out of the driveway, hearing the police sirens becoming closer. When the police detained him, he found some solace in the fact that they were out of this mess.
Legal complications hampered the allegations against Felix, despite Henry’s threats. The absence of the box cast doubt on several crucial aspects of Henry’s case. Felix waited for his court date in a detention cell for four months. A guard informed him one day that someone had paid his bail.
Felix was genuinely perplexed. Suzie was waiting for him in the front portion of the prison, where he followed the man. Together, they strolled outdoors. Mom was waiting for them, parked at the curb.
Felix replied, “Okay, Suzie, I can’t wait any longer,” as they climbed into the vehicle. “What’s happening?”
“Well, I ignored your advice regarding the box.” Suzie gave a shy smile. Rather, I discovered how to open it. There was a note from Mrs. McAllister along with an authentication certificate inside. Dad, she genuinely wanted that package to belong to you. That was stated in the note.
Felix scowled. Suzie wasn’t done, so he didn’t have much time to consider Mrs. McAllister’s request that he take the box, even though he still didn’t comprehend it.
“I showed your lawyer the note, and after that, I brought the box containing all the documents to an antique dealer.” Suzie gave this big smile. “He gave us enough money to post bail, and we have an additional $100,000!”
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