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
This Girl Became a Successful Child Star after Bio Parents Gave Her up to Family Who Had ‘No Plans’ to Adopt
When she was a newborn, his celebrity’s biological parents placed her for adoption.
Because their occupations meant more to them than raising a child, the star’s birth parents didn’t want her when she was born.
Up until the truth was revealed, the actress’ adoptive parents had been lying about her background.
The French Hospital in Los Angeles, which is now defunct, was the hospital where the future celebrity was born on May 8, 1964. The actress was adopted by Barbara Crane and Paul Gilbert, who took her in when she was just 24 hours old.
Jonathan, her younger brother, was also adopted by the couple. Barbara was a twentysomething actress whose career was cut short, and Paul was a stand-up comedian, actor, and dancer who began as an aerialist with a family circus from Buenos Aires. Barbara and Paul parted ways when the young child was six years old, but his daughter remembered him with affection, saying:
“I have never known a more brilliant, energetic, humorous, loving, and fair person than my father.”
When Paul passed away in 1976, many believed he had suffered a stroke while in bed. Her adoption was made public. The celebrity claimed in her book “Prairie Tale: A Memoir” that she was informed when she was a young kid that her father, David Darlington, had been a Rhodes Scholar and that her biological mother, Kathy Wood, was a prima ballerina.
Her birth parents reportedly had no desire to give up their occupations in order to raise her, according to her adopted parents. The timing of the celebrity’s birth was allegedly incorrect, and as a result, they had to give up their daughter because her father was in the middle of a project.
She learned the whole truth about her biological parents when she was old enough. Although not a prima ballerina, her birth mother was a dancer, and David was a stock car racer and sign painter.
Kathy and David had three children between them when they were first married to other people. After running away, becoming pregnant, and moving in with their kids, the couple realized they couldn’t support a seventh child.
Parents Who Adopted Her Didn’t Want Her
The actress was stunned to learn more about her adoption after the death of her adopted father. Mitzi, her godmother, talked about the day she was picked up from the hospital by her adoptive parents.
She acknowledged that when the Gilberts returned with their new baby, it came as a shock. This astonished the actress, who looked to Barbara, along with other family members, and she confessed:
“Well, we weren’t planning on adopting a kid.”
When Barbara and her husband received a call informing them that the little girl will be available, they replied they weren’t seeking for a kid. When the celebrity’s adoptive mother phoned her out-of-state spouse, he instructed her to “go get it.”
She said to the journalist that she wouldn’t subject her kids to the burden of such a dark secret.
She was taken aback to hear herself referred to as a “it,” but Barbara clarified that she hadn’t even been born yet. Later, after learning of her upcoming arrival, Barbara revealed to her that they had been attempting to conceive.
Barbara claims that although the Gilberts were undergoing fertility treatments, they had not brought up the subject of adoption until they got the call. The actress discussed the secrecy of her adoptive family in an interview from July 2020.
The Secrets of the Family
The famous person disclosed to “CBS Sunday Morning” that she learned at the age of 11 that her father had passed away due to a stroke. But she found out at 45 that he had committed suicide.
The actress concealed the secret from everyone in her life, even herself. She informed the interviewer that she would never subject her children to the harm that such deep secrets do to families.
To learn the truth about what had happened to her adopted father, the actress engaged a detective. The detective learned that the deceased World War II veteran had threatened to take his own life while receiving care from the VA and was in excruciating pain.
She fought the anguish of losing her father in this way for approximately six months after learning the truth about Paul. During that time, she was unable to eat or sleep. She has since come to terms with it, though, and now works to preserve his memory by supporting mental health awareness and suicide prevention.
On January 23, 1982, an actress was spotted in Santa Monica at the Santa Monica Bowling Alley | Source: Getty Images
The actress also accepted and forgave Barbara for her decision to conceal the truth, even though she had been angry and betrayed for a long time. The next chapter reveals the celebrity’s name and her current way of life.
Who Is the Star Who Got Abandoned and Went on to Become a Famous Actress?
Melissa Gilbert is the actress, best known for her role as Laura “Half-Pint” Ingalls Wilder on the adored television program “Little House on the Prairie,” which ran from 1974 to 1983. She published her memoir, “Back to the Prairie,” in July 2022, and she is currently spending time with her family.
The celebrity acknowledged that she is “blessed” and mentioned that she is in a different place from her deceased adoptive father. She wants Paul to have felt the happiness that comes with having grandkids and the value of having a life partner who makes you feel listened, safe, and loved.
Timothy Busfield, Melissa’s third husband, and she became grandparents to a total of eight grandchildren in May 2022. While going through his second divorce, Busfield observed the actress waiting for a buddy at an empty pub in 2012.
On June 20, 2023, in Monte-Carlo, Monaco, Melissa Gilbert and her spouse Timothy Busfield attended a photocall for the 62nd Monte Carlo TV Festival | Getty Images
In April 2013, the pair got married in an intimate ceremony in Santa Barbara, California, with Melissa donning a dress by Morgane Le Faye. When Barbara’s daughter couldn’t determine what she wanted, Barbara suggested the brand’s Santa Monica store.
She disclosed in her book “Back to the Prairie” that Busfield, dressed in a blue suit, was alone at the private event; no guests were present. After nearly a lifetime in Hollywood, the famous person had her first kid, a son named Dakota Paul Brinkman, from her first marriage to the actor Bo Brinkman.
Michael Garrett Boxleitner is Melissa’s second child, born after her marriage to Bruce Boxleitner. Along with being a father, Busfield raised three children: Wilson, Daisy, and Samuel. He and his wife currently reside peacefully in a 14-acre cottage in the Catskill Mountains of New York.
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