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
Little girl was abandoned by dad who said she was ‘dead’ to him – now she’s a famous actress
In 1975, a well-known musician met iconic actress Goldie Hawn at the height of their careers.
The two crossed paths while traveling from New York to Los Angeles on a first-class flight, and their connection was immediate.
The musician, a member of The Hudson Brothers, was already a prominent figure in the music world, having performed alongside The Beach Boys, The Osmonds, and The Monkees. In addition to his music career, he also appeared in films and TV shows, most notably the cult classic Hysterical.
Recalling their first encounter, the musician described the chemistry as undeniable. “The attraction was instant. I invited her out to dinner that night, and that was it,” he shared. Their relationship quickly escalated, with their physical connection being a central aspect.
“The [intimacy] was mind-blowing. Even when everything else in the relationship turned sour, the [intimacy] was always amazing,” he added, per the Daily Mail. Though their relationship had its ups and downs, there were moments when it seemed as though they were making progress.
The couple married in 1976 when Goldie was pregnant with their first child, a son. However, their son’s birth was not without complications. Born at Cedars-Sinai Hospital in Los Angeles, he was diagnosed with meconium aspiration, a life-threatening condition in which a newborn inhales amniotic fluid contaminated with meconium.
The newborn was isolated for three days after birth, which deeply distressed the couple. “Goldie and I were beside ourselves,” the musician remembered. He further explained: “She was really sick, and I’d go from her bedside to the neonatal intensive care unit. The doctors didn’t think [son’s name] would make it. But [he] pulled through, and from that moment, he was our precious miracle.”
Three years later, the couple welcomed their second child, a daughter, in 1979. The family of four enjoyed several happy years together, but their marriage came to an unfortunate end in 1981 when the musician discovered Goldie had been unfaithful. The musician longed for a traditional marriage, which conflicted with Goldie’s views on commitment.
“Goldie was having affairs, [and] she told me pretty much on our wedding night that she wanted an open marriage, that she couldn’t imagine being faithful to one man for the rest of her life,” he revealed to the Daily Mail. “I wanted a traditional marriage, but Goldie couldn’t settle. Eventually, I moved out.”
After their split, Goldie began dating actor Kurt Russell in 1983. They had initially met in 1968 while filming The One and Only, Genuine, Original Family Band, but it wasn’t until their reunion on the set of Swing Shift that their romantic relationship blossomed. Their son, Wyatt Russell, was born in 1986, three years into their relationship.
Blending their families proved to be a significant adjustment. Goldie’s daughter recalled: “For me, it felt like such a big moment because it was like, ‘My mom is madly in love with this guy.’” She added: “And I was meeting his son [Boston], which meant, ‘Does this mean that this is my brother?’ It was a lot to handle at such a young age.”
Goldie’s children from her previous marriage struggled with feelings of abandonment after their parents’ divorce. Her son recalled how their biological father gradually distanced himself from their family. Reflecting on a controversial Father’s Day post dedicated to Kurt, he said: “It doesn’t really matter which one of these men is my father. My pa stepped in when I was six and made me the man I am today.”
Both siblings have fond memories of Kurt stepping into the role of father figure. Though their relationship with their biological father, Bill, remains strained, they often express gratitude for Kurt’s dedication.
Meanwhile, Bill has openly voiced his feelings of betrayal, accusing Goldie of “poisoning” their children against him. Despite the tension, Kate and Oliver are focused on healing from their past and maintaining a positive outlook for the future, per Hello!.
By 2015, the strained relationship with Bill became public when Oliver posted a controversial Father’s Day message on social media. He shared a throwback picture of himself, Kate, and Bill, captioned: “Happy abandonment day… @katehudson.”
Bill, angered by the post, expressed his frustration in an interview, saying: “Oliver could have picked up the phone and called me, but he hasn’t. This was clearly premeditated; he chose the photograph and posted it on Father’s Day when he knew it would cause maximum pain.”
Bill went further to claim that if Oliver wanted to cut him out of their lives, he had succeeded. The fallout only deepened when Kate followed Oliver’s lead and posted her own tribute to Kurt, which added to the tension.
Kate appeared on Howard Stern’s show, speaking about how Kurt was the father who was present during the difficult and challenging times. In response, Bill stated, per the Daily Mail: “I would ask them to stop using the Hudson name [because] they are no longer a part of my life.”
He further expressed: “Oliver’s Instagram post was a malicious, vicious, premeditated attack; he is dead to me now, as is Kate. I am mourning their loss even though they are still walking this earth.” Following this, Bill decided to remove all childhood memorabilia of Kate and Oliver from his home, according to the Daily Mail report.
Despite the distance between Bill and his older children, Kurt has embraced his role as a grandfather to Kate and Oliver’s children.
While Bill continues to harbor resentment, Kate and Oliver have moved on, choosing to focus on the family bonds they’ve built with their stepfather, Kurt.
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