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
“When you have a broken heart – at least when I do – you got to get it out of your system. You want people to sympathize with you. I was at rock bottom, in the middle of hell.”
Rumors of a breakdown dogged Blake Shelton and Miranda Lambert’s brief marriage. Both are now contentedly wed to separate partners.
Given their prominent positions in the music industry, it is understandable why Blake Shelton and Miranda Lambert fell in love so soon.
Even though he was still married when he met her, their shared love of music drew them together. Their love affair ended in divorce eventually.
Following their introductions at CMT’s 100 Greatest Duets Concert, the two musicians first came into contact with one another in 2005.
From the beginning, she was drawn to him, but he ignored her because he was married. In a similar vein, Shelton was instantly smitten with the “Drunk” singer.
The beginning of their romantic tale
In a subsequent interview, Lambert claimed to have seen Shelton’s wedding photo in Country Weekly and to have known he was married. She continued, saying:
“I should have known better—this is forbidden. For crying out loud, my folks work as private detectives. I’ve witnessed affairs my entire life. I am one of the few who can truly know better than this.
Even still, she was powerless to ignore the “inevitable chemistry” they shared from the start. Shelton separated from his wife Kaynette Williams a year later and went after Lambert.
Shelton asked Lambert to marry him in 2010, but he did so in remembrance of her father. The “God’s Country” singer gave Lambert’s father a call to get his OK before proposing on May 9 and bringing out a platinum and diamond ring that he had personally picked out.
“It’s so much more perfect than I could have picked myself, but we’ve been together for five years, so he knew exactly what I wanted,” Lambert remarked. The country music artist cherished the casual party that was the proposal.
Apart from that specific instance, 2010 was an exceptional year for Lambert, as she achieved her first number one song, “White Liar,” in January and won both Album of the Year and Top Female Vocalist at the ACM Awards.
The pair married in 2011, but problems soon arose in their union. Rumors of a breakup surfaced in 2013, which the couple refuted.
In order to demonstrate that there were no secrets in their marriage, the “The Voice” judge at the time said that his wife had access to his phone anytime she wanted. He declared:
We truly do have that level of trust. Nothing is hidden. “Go search through my drawers or my computer if you feel like it,” is what I’ll say, and it’s been extremely helpful since I don’t want her to ever question anything.
Even though there were still rumors in 2014, the pair didn’t seem to be affected and even made jokes about the supposed divorce. In the past two years, Lambert joked, “I think I’ve had like five sets of twins and we’ve been divorced four times, and one of us had a $100 million divorce.”
Shelton and Stefani were married in a modest chapel on the “Home” singer’s property in July 2021 in a private ceremony held in Oklahoma.
The pair sent heartfelt wishes on social media to commemorate their third wedding anniversary the same year.
Lambert acknowledged that marriage was difficult, but he also stated it was a wonderful gift that shouldn’t be taken too seriously. She continued, saying:
It is our constant goal to be together. On our anniversary, I wouldn’t want to be on the other side of the nation! That moment is precious.
However, the pair soon shown that there was turmoil in paradise, proving the claims to be real. Gwen Stefani collaborated with Shelton as a coach on season nine of “The Voice” in April 2014.
After four years together, Shelton and Lambert announced their divorce within a year. They said in a statement that was released:
We are actual individuals with actual lives, families, friends, and coworkers. As a result, we respectfully request your understanding and privacy in this very private situation.
The couple disclosed that they were surprised by the split and that they had to take a risk by choosing to continue living their lives on their own.
Both before and after the publishing of the statement, Shelton and Lambert said nothing about the matter. They had ten wonderful years together, including their courtship phase.
LIFE AFTER PARTNERSHIP
Shelton quickly started dating Gwen Stefani, his co-star on “The Voice,” following their breakup. On November 4, 2015, they made their relationship official via Shelton’s agent, who stated:
“Gwen and Blake have been friends for a long time, but they recently started dating.”
The couple claimed that their congruent divorces and life events strengthened their bond.
Shelton eventually told Lambert about his divorce in 2020. Details regarding their breakup were disclosed in his song “If I’m Honest.”
He answered, “Maybe not specifics.” However, you get the gist of it. It is my chronicle of divorce, but perhaps even more than that, it is also my record of happiness and infatuation.
He’s got to admit that his second divorce has devastated him to the point of no return. Even though Shelton did not create the song “She’s Got a Way With Words,” which describes a partner who strayed and lied, he isn’t stopping people from believing it was a reflection of his own relationship. He declared:
“You have to let go of it when you’re feeling down, or at least that’s how I feel. You want to be able to relate to other individuals. I was in the midst of hell, at my lowest point.
But there was also someone who understood him quite well. It was a day he will never forget. “Gwen, who I didn’t really know, had these enormous tears in her eyes when I looked at her. It struck me, “Wow, she really feels bad for me.”
The singer of “Candyman” had recently filed for divorce from Gavin Rossdale, her husband of 20 years. Later, she spoke with Shelton by herself, and that’s when their close relationship began.
As time went on, their friendship grew; they went from communicating their understanding to exchanging emails once a week. He declared:
“Then I wake up, and she’s my entire world, and I wonder if she feels the same way about me.”
Shelton and Stefani were married in a modest chapel on the “Home” singer’s property in July 2021 in a private ceremony held in Oklahoma. Luckily, Stefani’s family and kids adore her new husband and have a wonderful impact on her. Says she:
“I’ve never had a more feminine style. I think it’s because I have a pretty macho man and I’m genuinely in love. Now that I’ve let that side of myself show, I enjoy it.
Within three months of their first date, Lambert also wed Brendan McLoughlin, an officer in New York City. Even though he was married when they initially met, their love remained. It was made public in 2022 that the couple was attempting to conceive.
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