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
My Sister Betrayed Me Twice to Help Our Evil Father – Story of the Day
I never liked my own family—call it dysfunctional if you may. But I still couldn’t fathom how my sister would betray me like this, twice, even though I helped her and our father out.
Sometimes I wonder what would happen if I was born into a better family. You know, with better parents who actually know how to be parents? But you don’t always get what you want in life, isn’t it?
I can’t really blame my mother actually—she ran away from the family when I was just ten, presumably since my father was abusive and manipulative. I still wish she took me and my sister away with her at that time, but then again, it is what it is. Sometimes there’s no use in looking back at things and constantly thinking about “what could’ve been.”
That’s what my therapist kept telling me. Don’t look back on the things you can’t change and think about what could’ve been. Look forward, time is linear, there’s no going back.
But she also said writing it out might help—so here it is, I guess.
I grew up in a dysfunctional family | Source: Shutterstock
As I said, my father was an abusive and manipulative monster—self-centered, arrogant … he only cared about himself and the things that actually concerned him. Sometimes I wonder how come my mother actually married him. That’s something I’d never find out, I guess.
As for my younger sister Cheryl, you can probably understand what kind of person she’d grow up to be under such circumstances. We were close when we were kids—at least before everything happened —but after my mother ran away, it had gotten worse since then.
My father never liked me since I was a kid, but he hated me even more after my mother ran away. Why? I have no idea. He probably thought I was the reason why she ran away—he never thought it was his fault.
Well, he blamed the stripper when he was drunk sometimes, but it takes two to tango, isn’t it? Or that it took two to have a lapdance, in this context.
Anyway. My sister Cheryl.
Cheryl and I used to be close when we were kids | Source: Pexels
Ever since mother left, Cheryl became dad’s favorite, presumably since she was still too young to understand what happened. Since I was too old to be converted into daddy’s little girl at that time, he focused on Cheryl instead.
That’s what I meant when I said things began to go downhill from there—he and Cheryl began to gang up on me, alienating me in the house. It wasn’t pleasant, and to be honest, I don’t really want to go into details about what happened. Let’s just say I wish I had a more functional family.
Cheryl grew up to be a spoiled brat. That’s the thing about my father. He might be an absolute jerk of a person, but he wasn’t stupid. In fact, he made himself a fortune by setting up a trading company. It made sense though since he had every single trait of being a psychopathic CEO.
Chery, being daddy’s little girl of the family, had everything she needed and wanted—and even things she didn’t know she wanted. I can still remember the Gucci bag my father gave her when she was just 12. Can you believe that? A 12-year-old girl holding a Gucci bag?
Needless to say, Cheryl grew up to be a dysfunctional human being.
I remember how I used to smell like fast food every night after work | Source: Pexels
As for myself, I had to work hard for everything that I had. Since I wasn’t getting any allowances from my father, I began taking up part-time jobs here and there just to get by. I worked in McDonald’s, Wendy’s, and even handed out leaflets outside Sears at some point. I can still remember how I used to smell like French fries after my shifts. You just cannot get rid of that stench.
In a way, I am thankful for the experience, since all of these things taught me things I needed to know in life. It made me who I am—it taught me how to be resilient and got me through some dark times.
I moved out as soon as I could. I remember I was 18 at the time—it was a long and hot summer, and I packed up my things and went off to California in my old Honda Civic without even saying goodbye. I probably had $400 in my account at the time, but it was liberating. I can still remember the sweet summer breeze of youth and freedom along the Pacific Coast.
I found myself an IT job in California | Source: Pexels
Fast forward 10 years from there, I got my college degree and began working for an IT company. I wouldn’t say I had a great career, but I managed to have a decent life and save some money of my own. To be honest, I wouldn’t stay in IT if not for the money. But hey, we all gotta make a living somehow.
It was then when I received an email from Cheryl. I hadn’t spoken to her nor my dad since the day I moved out, not that they cared anyway. They could’ve reached out to me somehow, but they did not. Ten years, not a single message from them.
But surprise surprise, Cheryl actually asked me for help in the email. How things have changed, I thought to myself.
It started with a bunch of formal addresses like “Dear Emma,” “I hope this email finds you well,” and my favorite—“Sincerely yours.”
I received an email from Cheryl while at work one day | Source: Pexels
She was asking me for money since her kid got sick and needed surgery, but her ex-boyfriend ran away with some chicks and left her with nothing. She said she hadn’t been talking to dad for a few years already due to some argument … bla bla bla. That was why she needed my help.
I was hesitant at first, but then I opened the attachment in the email—it was a picture of my nephew. He was adorable.
After looking at that picture, I debated on what I would do—or rather, the right thing for me to do. You see, I might not like my family, but the kid was innocent. He shouldn’t be pulled into the whole family feud that we had.
After a night of turning over and over again in my bed, I decided to wire her the money.
Cheryl didn’t respond to my emails after I wired her the money | Source: Pexels
The next month I sent her an email, asking her if everything was alright with the kid—alas, no response.
So I did a bit of research and found out where she lived. Well, as it turned out, she didn’t move far—basically six or seven blocks from where we used to live. I decided to drop by and give her a visit.
It had been more than ten years since I left—but that’s the thing about small American towns … scenery might change, but people don’t. I can still recognize the same shops and people I used to know. Older, but not necessarily wiser.
Then, as if God intervened through some twisted manner, before getting to Cheryl, I bumped into an old classmate of mine who happened to know my family cause you know, small town.
I bumped into John at a gas station—it was truly a strange coincidence | Source: Pexels
John was a classmate of mine back then. His mother and my father were neighbors growing up, so he was kind of a family friend. He was beyond surprised when he saw me at the gas station.
“Hey. Is that you, Emma?” he said as he approached me from his car.
“ …John? God, could barely recognize you there, man,” I said.
“What brought you back here? Haven’t seen you in years,” he continued. “Came here to see your old man?”
I assumed he didn’t know what happened to my family all these years.
“Nah, just wanna check on Cheryl and my nephew,” I said, trying to shrug it off and make it sound as natural as I could.
“Your nephew? I didn’t know Cheryl had a kid,” responded John, with a pair of confused eyes. “That’s strange, I would’ve known since I live across the road from her,” he added.
Now things were getting weird.
John happened to live across the road from Cheryl | Source: Pexels
Out of curiosity, I asked John about my father after a brief explanation that we haven’t been talking for quite a few years.
“Yea, he goes over to Cheryl’s every weekend. His business partner screwed him over, I heard, so he lost quite a bit of money there. He seemed sad for a while but he seems alright now,” he said. “I think Cheryl managed to bail him out or something.”
“His partner screwed him over? When was that?”
“Maybe a month or two ago? I remember seeing him walking around Cheryl’s driveway, calling and cursing at his phone—must’ve been around that time.”
I decided to pay Cheryl a visit. I had to know what happened.
I knocked on Cheryl’s door, not entirely sure what I was expecting | Source: Pexels
So, I pulled up in front of Cheryl’s house, rang the doorbell, and she opened the door for me.
From the door I could see my father sitting in the living room, having a glass of wine in his hand—and no, I did not see any kid in the house.
Cheryl was surprised to see me there, as you can guess by now. “Emma? What’re you doing here?” she asked.
“Just trying to check up on my nephew,” I responded.
For a fleeting moment, I could see it in her eyes that she was trying to avoid the topic.
“Oh, a friend of mine is babysitting Anthony now,” she responded. “Do you want to come in? We haven’t seen you in years,” she added.
I was still hesitant at the time—just one step, and I could step inside the house and perhaps deal with all that trauma sown within me years ago. It was so close, that feeling of being able to make things right at last.
But I wasn’t ready. I told them I was a bit under the weather and got back into my car and drove to a nearby motel.
Unable to face Cheryl and my father, I drove to a motel nearby for the night | Source: Pexels
The next day I bumped into John again at a local diner. God certainly works in mysterious ways.
But it was a bit different this time—when he saw me at the diner he simply turned around without saying a single word.
That was strange, I thought to myself. Considering we were on good terms the whole time, there was something odd about it. I decided to walk towards him and asked him what’s up.
“Hey man, sup? Is everything alright?” I asked him when he sat down at his table.
He tried to avoid having eye contact with me, but I just stood there, utterly bewildered by his reaction.
“Hey, I know it’s none of my business, but I think you might need some help,” he said.
Now this just got way more confusing.
“What? Why? I don’t think I understand,” I said.
“Look, I talked to Cheryl last night, about her having a kid—she told me that … well, she told me why you left,” he said meekly.
“What? What did she say?”
“She said you were … imagining things, and they had to send you away to the hospital.”
“W—what? How?”
I bumped into John again in the diner, but I could tell that something was wrong | Source: Pexels
“She doesn’t have a kid and I don’t understand why you said she has. So last night I went over to her place and asked her about it, and she told me what happened,” he said, but then he paused for a moment. “She said you just showed up out of nowhere and started asking about her kid … Look, I don’t want any trouble here.”
That … wretched woman. I don’t know if I can still call her my sister anymore. Did she just throw me under the bus after all I did for her and presumably our father? Am I hallucinating? No, I was pretty sure I was not.
“Wait a second,” I said to John as he was about to leave. I then went through my inbox and showed the email to John. He looked at it and went quiet for a while. But at last, he responded.
“Look, it’s really none of my business, just leave me out of this,” he said, and he simply left the diner without touching his pancakes.
Here I am, back in San Francisco, wondering if I did the right thing | Source: Pexels
So here I am, back in San Francisco at my own apartment. I just drove all the way back here after that interaction with John—Lord knows what other folks in town were talking about right now. Can you imagine that? My very own sister, fabricating a lie so that I could save our father who never cared about me, and then throwing me under the bus and telling the folks that I was crazy? Seriously?
I am not sure how I should feel about it—I admit that writing it down did make me feel better. But still … I couldn’t help but wonder if it would have made a difference if I actually walked into the house and talked to them. Maybe I had a chance to change something? Maybe things wouldn’t end up the way they are now?
I don’t know. I really don’t know.
What can we learn from this story?
Sometimes we just have to let things go. It is what it is, sometimes there’s just nothing we can do about it. Let go and start living.
Look forward. We cannot change the past, whatever that is, but we can try and move on, one way or another.
Share this story with your friends. It might brighten their day and inspire them.
If you enjoyed reading this, you might also enjoy this one where a man sheltered a homeless woman and discovered who she really was.
Leave a Reply