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
Elliot Page’s Journey Into Finding His New Life in a Male Body
Actress Ellen Page made a remarkable change on her social media profiles on December 1, 2020, revealing a new male identity as Elliot. This unexpected transformation quickly gained widespread attention as Elliot’s posts began circulating online. Netflix promptly responded by updating the credits of their movies and series to acknowledge this change. On Twitter, an outpouring of support was evident, with a post expressing immense pride and love for the newly emerged Elliot.
Life in the body of a woman
Achieving success in the film industry while presenting as a female, Paige made a remarkable entrance into the world of acting at the tender age of 10. Her inaugural role as Maggie MacLean in Pit Pony proved to be an instant triumph, garnering her a nomination for the esteemed Young Artist Award and paving the way for numerous exciting career prospects. By the time Ellen reached 18, she had already amassed an impressive repertoire of over a dozen roles in diverse movies and television shows, a testament to her exceptional talent and unwavering commitment to her craft.
Page’s career reached a significant milestone with their prominent portrayal in the film Juno. Esteemed film critics showered Page with praise, recognizing their “astonishing talent,” while the movie itself was hailed as one of the standout films of the 2000s. At the young age of 20, Page made history as the fourth youngest nominee for the prestigious Academy Award for Best Actress, a truly remarkable accomplishment.
The start of a new life
Despite outwardly achieving success, Page grappled with a sense of incompleteness. From a young age, they carried a profound awareness of being different. Even in childhood, Page felt a stronger identification with being a boy, going as far as signing their name as Jason and expressing to their mother the desire to grow up as a man. Despite the passage of time, the persistent question of identity and the ongoing struggle for self-acceptance regarding their gender remained steadfast.
Just prior to reaching the age of 27, Page chose to share a personal revelation with the public. Initially, he openly acknowledged his attraction to women and subsequently disclosed that he had discovered his ideal partner in dancer and choreographer Emma Portner, whom he married in 2018. The trajectory of their relationship has been unconventional, as Portner had previously been married to a woman and divorced a man. However, the couple ultimately separated in 2020, with their divorce being finalized in early 2021.
Life in the body of a man
With unwavering courage, Elliot Page took to his social media platforms on December 1, 2020, to reveal his authentic identity as a man. Embracing the pronouns he/they and adopting the name Elliot, he fearlessly shared this significant decision with the world. The response was overwhelmingly supportive, with fellow celebrities and individuals alike recognizing him as a beacon of inspiration for transgender and non-binary communities. Even his spouse publicly expressed deep admiration, acknowledging the invaluable presence of trans, queer, and non-binary individuals as a precious gift to the world.
In another groundbreaking milestone, Elliot Page achieved a historic feat by becoming the first transgender man to be featured on the cover of Time magazine. For this momentous occasion, he made a deliberate choice to collaborate with a photographer who could genuinely grasp his unique experience and authentically capture his essence as a transgender man.
During an interview with Time, Elliot openly and sincerely shared details of his personal journey, including his gender-affirming surgery, which he described as not only transforming his life but also serving as a lifesaving intervention. Finally able to embrace his true identity as a man, Elliot expressed that he has always been the person he is today, deeply rooted within himself throughout his entire existence.
Elliot expresses his genuine excitement about being able to act as his authentic self in his own body, remarking, “No matter the challenges and difficult moments of this, nothing amounts to getting to feel how I feel now.” Finally living in harmony with his true self and appearance, Elliot’s life is now enriched with moments of pure joy that were once absent. Simple, everyday things like coming out of the shower with a towel wrapped around his waist now bring him happiness. Looking in the mirror, he can confidently say, “There I am,” as he revels in the newfound joy of being true to himself.
Undergoing the surgical transformation had a profound impact on Elliot, not only in terms of his physical appearance but also in igniting a newfound wave of creativity within him. Ever since coming out to his loved ones, he has been infused with a powerful sense of inspiration, leading him to embark on various creative endeavors.
This includes writing a film script, exploring his passion for music, and actively working on a memoir that aims to empower and uplift numerous individuals. While engaged in his work on set, Elliot has found that, apart from feeling at ease in his male body, there have been no significant changes to his professional experience.
Why Page talks about it so much
Elliot is often credited with inspiring numerous transgender individuals to embrace their true selves, but the actor holds a different perspective. Despite the overwhelming support received upon coming out, Page sees himself as an activist fighting for the rights of transgender people. He aims to raise public awareness about crucial issues using his platform and privilege. As he expressed, “My privilege has allowed me to have resources to get through and to be where I am today and, of course, I want to use that privilege and platform to help in the ways I can.”
In an interview, Elliot was posed with a thought-provoking question about what message he would convey to his younger self if granted the chance to travel back in time. After careful consideration, the actor responded with profound introspection, expressing, “I would assure my younger self that I was precisely the person I perceived, felt, and understood myself to be.”
But Elliot page isn’t the only famous person to transition, since there have been many before him and will be many after him. And it’s inspiring to see them flourishing after going under such a transformation. And sometimes actors have transformed themselves simply for a role, where the result was jaw-dropping.
Preview photo credit Ninha Morandini / Wikimedia Commons, CC BY 2.0, elliotpage / Instagram
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