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
Remembering the Stars Who Have Died Since Appearing on ‘Celebrity Rehab with Dr. Drew’
Since the VH1 reality show’s 2008 debut, twelve of its alumni have passed away.
Celebrity Rehab was founded by Dr. Drew Pinsky to counter the tabloids’ depiction of addiction, according to a 2009 New York Times article on the set of the show. Pinsky, 65, was first opposed to the concept of receiving treatment on television. Following the premiere of the first season of the show, the addiction medicine expert told PEOPLE about his friend, counselor Bob Forrest, who persuaded him to get treatment: “He said, ‘I am so tired of people talking about rehab who have no idea what they’re talking about.’” They are unaware of the struggles and addictions that celebrities face.
The VH1 series, which ran from 2008 to 2011, featured a number of celebrities addressing their substance misuse problems in the Pasadena Recovery Center in California with Pinsky. Celebrity Rehab featured prominent artists, actresses, sports, TV celebrities, models, and more throughout the course of five seasons. Regretfully, following their performances on the reality show, twelve celebrities have passed away. Let’s examine their lives in more detail and how they openly discussed their difficulties in an effort to assist others.
If substance misuse is a problem for you or someone you know, please call the SAMHSA helpline at 1-800-662-HELP. Please call the 988 Suicide and Crisis Lifeline at 988, text “STRENGTH” to the Crisis Text Line at 741741, or visit 988lifeline.org if you or someone you know is thinking about taking their own life.
Dim-witted Shellshock
It’s funny how life tricks us, isn’t it? The frontman of Crazy Town, who was well-known for being insane both on stage and, regrettably, off, died in June 2024 at the age of 49. Shifty went in and out of dangerous circumstances during his career, including comas and DUI accusations. It was heartbreakingly obvious how much cocaine and medications affected him. “If I kept at it, I was going to die,” he once said to PEOPLE. My goal is to remain sober.
Tom Sizemore
On March 3, 2023, Tom Sizemore, the guy whose Golden Globe-nominated performances could have you riveted to the screen, passed away. His struggle with drug usage was more tragic than amusing. Paul, his brother, said, “He was bigger than life.” More than anyone I know, he has impacted my life. I am heartbroken by his passing and will always mourn him.
Frankie Lons
Every child’s worst dread is to watch their own mother battle addiction before giving in to it. Frankie Lons, the mother of Keyshia Cole, had a turbulent life. What a horrible irony it was that she died on her own birthday. The emotional Instagram post from Elite Noel, her daughter, stated it all: “My mother in a body bag on her birthday is the worst anguish I have ever experienced! My heart ached so much.
Kitaen Tawny
At the age of 59, actress and ’80s star Tawny Kitaen passed away quietly at her Newport Beach home. Her children Wynter and Raine verified their grief with a statement, “You gave her life every day,” following her diagnosis of dilated cardiomyopathy. We love and miss her, and we are aware that her legacy will endure forever.
McKibbin, Nikki
Do you recall Nikki McKibbin from the inaugural season of American Idol? She was generous enough to give her organs before she went away at the age of 42 from a brain aneurysm. Craig, her spouse, put it poetically: “Even in the end, she is still giving.” An appropriate homage to a giving person.
Jason Davis
At the age of 35, the voice actor that embodied a character in Disney’s Recess passed away from fentanyl overdose. His mother remembered him as a season 4 participant who “had a true heart of gold with such a zest for life.”
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Chyna
On April 17, 2016, Chyna, a formidable WWE performer, passed away. The mixture of drugs in her system was the accidental offender. Her life served as an example of publicly facing one’s inner problems while clinging to hope.
Mindy McCready
On February 17, 2013, Mindy McCready, a country music vocalist with a beautiful voice, suddenly passed away. She dealt with alcohol and opioid addictions on the show, and her end was clouded in sadness following the suicide of her boyfriend. A terrible domino effect.
Joey Kovar
Joey Kovar, a reality star from The Real World: Hollywood, passed away suddenly at the age of 29. A life that appeared to be headed toward happiness was ended by opioid abuse. With regret, his brother remarked, “He had turned into such a happy person.” I’m still not really clear what transpired.
Rodney King
On June 17, 2012, the civil rights activist passed away at the age of 47. King’s stress from the vicious assault he suffered in 1991 at the hands of LAPD cops drove him to battle substance usage. Alcohol, marijuana, PCP, and cocaine all had a nasty part in his death; he was discovered drowning in his swimming pool.
Jeff Conaway
The well-known face of Grease actor Jeff Conaway concealed personal troubles. On May 27, 2011, the man who lighted up Broadway and little theaters alike passed away. He battled his addictions all the way to the end, but his job and the people in his life gave him comfort.
Mike Starr
To wrap up this solemn homage, on March 8, 2011, Alice in Chains’ Mike Starr overdosed on prescription drugs. Friends, family, and fans came together for an open memorial service in Seattle to honor a life that inspires people via music.
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