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
Following his purchase of a dinner for over $600 I blocked him but it turned out he was trying to warn me
Penelope’s evening seems to be getting more complicated by the minute, but then a simple dinner with David turns into a journey of shocking discoveries that challenge everything she has ever believed to be true about her family and herself. A dinner party that seemed to be going well suddenly becomes a platform for startling revelations that could change her life forever.Have you ever gone on an awful date? Indeed, I concur. This one started off really well, but let’s just say the conclusion went in a direction I wasn’t expecting. So it all began one seemingly ordinary day in the public library.
I got to know David in this way. With his teacherly charm, he started a conversation by asking me about my favorite literature. Before I knew it, we were deep in discussion on everything from classic literature to modern science fiction. It was nice to meet someone who could follow my meandering thoughts.
During our talk, David unexpectedly invited me out—not for a date, but for dinner. “Which restaurant is your favorite?” he said. I remember giggling softly, taken aback by his openness.
I responded, “My favorite place is a bit much for a first date,” but I eventually told him about it. I reserve this lovely spot for indulging in self-indulgence or celebrating personal successes. After all, you don’t typically spend $600 on dinner.
However, I wanted our first meeting to be casual, so I suggested a trendy Mexican eatery that was roughly halfway between us. I winked and added, “They have over 300 tequilas and tacos with handmade tortillas that are to die for.” It’s also quite reasonably priced.
David listened intently, but he was certain about choosing the spot. I appreciated his initiative as much as I wanted those amazing tacos. Compromise is necessary in big cities with awful traffic, especially if you live on opposite sides of the spectrum.
Now allow me to discuss my favorite restaurant. It’s this incredible location where James Beard award-winning mixologists deliver bite-sized pieces of heaven with their concoctions. Every now and then I go there just to enjoy a drink and take in the lavish setting.
David hesitated for a moment, then suddenly insisted on going to my favorite fancy restaurant. After all, who was I to argue? It is, after all, my favorite place. Thus, we departed.
The start of the evening was quite pleasant. We got the delectable little morsels I mentioned before as appetizers, and the cocktails continued to be intriguing.
Dinner was brought, dish after exquisite dish, and there was much joshing and animated conversation. We even had dessert, which is unusual for me unless it’s a really special occasion. We were clearly having a fantastic time, in my opinion.
But how did the evening unfold, my dear? After paying the significant amount, which was obviously more than $600, something unexpected happened.
My card slipped out of my bag and landed on the table out of habit. Things started to go weird after David took up the cause. Rather of simply handing it back, he examined it closely.
Then he did something that made my stomach turn to gravel: he examined every detail and stated, “You should be careful with this,” before putting the card down.
Upon further reflection, it’s possible that he had bad intentions. But it felt like a major invasion of my privacy at the time. Why did he have to be so indifferent to my card? Is there any way he could have given it back without saying something like that?
I quickly called it a night, feeling both humiliated and furious. I thanked him, if a little stiffly, got into a cab, and as soon as I arrived home, I blocked him. Nothing, not even a text or call.
I spoke with a friend about it today, and they said maybe I had been too hard on David. They said that I could have just asked him about it and that there might have been a good reason for him to look at my card.
But all I could think about at the moment was how he had ruined the whole evening and my mood. And so, while I was still thinking about the awful dinner, life decided to throw me another curveball.
Two days after I had pushed the block button on David, here he was, standing outside my house. You did hear that, that’s true. He seemed apologetic and uncomfortable, like he had something important to say.
When he murmured, “Penelope, I’m so sorry,” I could see he meant it by the look in his eyes. “I needed to make sure it was really you, Penelope Smith.”
I listened, confused as I was at this point, as he took a big breath and revealed something startling that would change my life forever. “I’m your half-brother,” was his reply, barely discernible above a whisper.
I tried to process what he had said while I blinked. How could David, the guy I recently turned down for the library date, be my half-brother? He said that the man I had always considered to be my father was not the one I was born with. Instead, it was his father who cheated on my mother. It sounded like something out of a soap opera.
The days that followed went very swiftly. We decided to have DNA testing done because this was a substantial enough claim to not rely solely on faith. The world did indeed have one more surprise in store for me when the results were in: we were, in fact, half-siblings.
My emotions were all over the place as I stood there clutching the results. I was not only surprised, but I also had an odd kind of curiosity for my unidentified half-brother. I wasn’t sure if I should tell my parents. Such details could disclose a lot of things.
In the end, I realized that some things are just too significant to overlook, regardless of the consequences. I made the decision to tell them, as I wanted, and on my terms. Meanwhile, David and I started to painstakingly create the sibling bond that none of us ever had.
Beneath the strangeness and discomfort, there was a relationship that was potentially just as important as the one I had expected from my meet-cute in the library.
Folks, that is all there is to it. A family gathering turned from a supper to a crisis of self. Is it not the case that life operates in peculiar ways?
In order to pay the bill, my significant other insisted that I give the server my card.
It was meant to be an evening of celebration exclusively. After six months at my new job, I was thrilled to finally inform my boyfriend Troy that I had gotten a huge raise.
He recommended the newest, posh restaurant in town, the one with the gorgeous interior and gourmet fare.
He said, “Lisa, let’s just get dressed and head out.” Since we don’t get to do this very often, let’s make the most of it.
We didn’t always choose to go out and do anything, I had to agree. This was not always the case.
“No problem,” I replied. “We really need to go out for a night.”
And I believed that we required it. Mostly because I had begun to see some signs of dissolution in our partnership, even though I wanted to believe that Troy and I were intended to be together forever. It felt, to put it simply, off.
Troy didn’t feel satisfied with his career, but I did.
During a salsa night one evening, he bitterly observed, “I do so much, but nobody bothers to recognize me.”
Troy sat on the couch, dipping his chips in the salsa and guacamole, and complained about his job for the entire evening.
Because of his opinions about my work, I refrained from complimenting him.
“Maybe you just need to give it more time,” I said, passing him a cool margarita alongside. “It’s only been a few months since you arrived.”
“Please,” he muttered to Lisa. “You were unable to understand. Give me room to exist.
But as I found out about this incredible chance, I was giddy with anticipation. I assumed Troy would feel the same about being recognized and having a celebration.
I was astonished when he told me he was proud of me and seemed sincere about it.
“Really, babe,” he said as he arrived to pick me up from my flat. “I admire you, and this is very important.”
The start of the evening was quite pleasant. Troy waited for me to finish getting ready before showing up with a bunch of roses. This was an exception to the rule that he disliked it when I took longer to get dressed than when he arrived.
“Come on,” I said. “I’m ready!”
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