53 Jokes For Pleaser

Updated on: May 08 2025

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In the bustling town of Jesterville, there existed a barber named Benny, known for his relentless desire to please his customers. One day, a new client entered, seeking a simple trim. Benny, eager to impress, unleashed a barrage of compliments as he snipped away.
"Your hair is so magnificent, it's an honor to work on such a masterpiece!" Benny exclaimed. The client, bewildered but amused, nodded in agreement. However, as the haircut progressed, Benny's enthusiasm reached new heights. "This hair, my friend, is a work of art. I'm not just a barber; I'm a hair maestro!"
The client, now adorned with a rather unique hairstyle, couldn't help but laugh. Benny, undeterred, handed a mirror, saying, "I hope you love it as much as I do. You're not just a customer; you're a walking masterpiece!" The client left the barber shop, turning heads and embracing the unintended avant-garde style.
Once upon a time in the quaint town of Mirthville, there lived a notorious pleaser named Oliver. His need to please was so profound that it bordered on the absurd. One day, he decided to bake a cake for his friend's birthday, aiming to outdo all previous birthday surprises.
The day arrived, and Oliver presented his masterpiece - a towering cake adorned with intricate decorations. As the birthday song commenced, Oliver, eager to please, attempted to carry the cake to the table. In a classic slapstick moment, he slipped on a banana peel, sending the cake airborne. It performed an impressive somersault before crash-landing onto the table, leaving everyone in stitches.
Amid the chaos, Oliver looked around with a sheepish grin, exclaiming, "I guess the cake really took the phrase 'party crasher' to a whole new level!"
In the pirate-infested waters of Jocular Bay, there sailed a peculiar pirate named Percy, renowned for his excessively polite demeanor. Percy couldn't plunder a ship without saying "please" and "thank you." His crew, though baffled, appreciated the politeness until they encountered a rival ship led by the dreaded Captain Snarltooth.
As the two pirate crews faced off, Percy, eager to please even in battle, shouted across the sea, "Excuse me, Captain Snarltooth, would you mind surrendering your treasure, please?" The opposing captain, utterly perplexed, responded, "Is this a jest, matey?"
Percy, determined to maintain decorum, replied, "Oh no, it's just customary to ask politely. But if you'd rather not, I completely understand." The standoff dissolved into laughter, as Captain Snarltooth couldn't fathom the politest pirate on the high seas.
In the whimsical world of Jokeburg, a magician named Marvin was known for his incredible tricks and equally impressive politeness. During one of his shows, Marvin attempted a daring escape act involving disappearing into thin air. However, things took an unexpected turn when, instead of reappearing on the stage, Marvin found himself in the mayor's office.
Panicking, Marvin apologized profusely to the bewildered mayor, saying, "I sincerely apologize for the inconvenience, Your Honor. It seems I've taken my vanishing act a bit too literally this time." The mayor, suppressing laughter, replied, "Well, Mr. Marvin, I appreciate the apology, but could you please disappear from my office now?"
With a courteous bow, Marvin performed a hasty vanishing act, leaving the mayor and his staff in stitches. The next day, the headlines read, "Magician Apologizes His Way into Mayor's Office – A Disappearing Act Gone Right!"
You ever meet those people who just can't say no? I mean, they're like human doormats. I've got a friend, let's call him Dave, but I should probably call him "The Pleaser." This guy can't turn down anything. You ask him for a favor, and he's like a politician during an election year – promises everything and delivers... well, not much.
Dave's the type of guy who, if you asked him to jump off a cliff, he'd be like, "Sure, do you prefer a somersault or a cannonball?" And you know he'd do it with a smile. I told him once, "Dude, you need to learn to say no." He said, "No problem!" See, that's the issue right there.
One day, I decided to test him. I asked him to help me move. Now, I live on the fifth floor, no elevator. Most people would've been like, "Hell no!" But not Dave. He showed up with a smile, a back brace, and a motivational playlist. We started calling him "The Human U-Haul." I even gave him a tip at the end, not in cash, but in a t-shirt that said, "I'm with Stupid." Because, well, you get the idea.
I've been thinking about starting a support group for Pleasers – call it "Pleaser Anonymous." Picture it: a room full of people sitting in a circle, introducing themselves like, "Hi, I'm Dave, and I'm a Pleaser." The group would probably plan a fundraiser, and Dave would be in charge of setting up the tables and decorations.
I can see the slogans now: "Just Say No... Sometimes." Or how about, "Putting the 'me' back in 'pleaser.'" We'd have a 12-step program, and step one would be learning to use the word "no" without breaking into a cold sweat.
But, you know what, despite all the craziness, we need Pleasers in our lives. They're the unsung heroes making the world go 'round, one overly enthusiastic "yes" at a time.
So, you think being a Pleaser is all rainbows and sunshine? Not when it comes to dating, my friends. I tried setting Dave up on a blind date. I told him, "Just be yourself, but maybe sprinkle in a little self-respect."
He shows up, and the girl's like, "So, what do you like to do for fun?" And Dave, with his Pleaser charm, goes, "Oh, whatever you like! I'm easy." She looked at him like he was a lost puppy. I asked him later how it went, and he said, "Great! We're going bungee jumping next week." Bungee jumping on the first date – that's not a date; that's a test of survival.
I told him, "Dave, you need to assert yourself a bit. Take charge!" The next date, he took her to a restaurant and said, "You pick the food, and I'll pick up the tab." Smooth, Dave, real smooth.
You know you've got a real-life superhero when you've got a Pleaser in your life. I mean, move over Spider-Man, we've got Dave, The Pleaser. His superpower? Making everyone else feel incredibly lazy and unhelpful.
I asked him once, "What's your secret, Dave?" He said, "It's simple – a crippling fear of disappointing people." Well, that's relatable. But hey, it works for him. He's like a human Swiss Army knife, ready for any task. Need someone to water your plants while you're away? Pleaser's got it covered. Want someone to proofread your novel about alien hamsters? Pleaser's on it, probably with a thesaurus and a red pen.
I've started giving him absurd challenges just to see if he'll say no. "Hey, Dave, can you juggle flaming bowling pins while riding a unicycle?" He didn't even hesitate – "Sure, I've been practicing." Who practices that?!
What do you call a pleaser with a time machine? A jest in time!
I asked a pleaser to tell me a joke about construction. They said, 'I'm still building up to those kinds of punchlines!
What's a pleaser's favorite game? Hide and seek... with punchlines!
Why did the pleaser go to comedy school? To brush up on their 'haha-has' and 'hehe-hes'!
I tried to out-joke a pleaser, but they said, 'You're in for a pun-derful surprise!
Why did the pleaser become a gardener? Because they wanted to grow a sense of humor!
I asked a pleaser if they could make a joke about stairs. They said, 'I'll step up to the challenge!
What do you call a pleaser who tells jokes in secret? A whisperer of whimsy!
Why did the pleaser bring a ladder to the comedy show? Because they wanted to reach new heights of laughter!
I asked the pleaser if they could make me laugh underwater. They said, 'Sure, I'll sea what I can do!'
What's a pleaser's favorite dessert? Punning cake! It's always layered with laughter!
What did the pleaser say to the grumpy joke critic? 'You need a humor injection!
How do pleasers apologize? They say, 'I'm sorry if my joke was a little too pun-ishing!
Why did the pleaser bring a pencil to the comedy club? To draw in the laughter!
What's a pleaser's favorite type of humor? Wordplay! They find it pun-derful!
I asked a pleaser if they could make a joke about time travel. They said, 'I'll let you know yesterday!
Why did the pleaser become a detective? They wanted to solve the case of the missing punchline!
Why don't pleasers ever get lost? Because they always find their way to the punchline!
I tried to challenge a pleaser to a joke-off, but they said, 'I'm a pleaser, not a teaser!
I told my friend a pleaser joke, and they said it was very uplifting. I guess laughter really does lift the spirits!

The Constant Complimenter

Feeling the need to praise everything, even when it's not warranted.
I praised a malfunctioning elevator. "What a creative take on a staircase!

The Over-Apologizer

Constantly saying sorry even when it's not necessary.
I'm so used to apologizing, I said sorry to a chair for accidentally kicking it. I swear it moved to let me pass.

The Agreement Enthusiast

Agreeing just to keep the conversation going.
I nodded so much during a conversation, I think I accidentally agreed to be a godparent to their pet goldfish.

The People-Pleaser

The pressure to always say yes and keep everyone happy.
I try to please everyone. I held the door for someone too far away, and now I'm just standing here like a doorman on a coffee break.

The Eternal Yes-Man

Saying yes without considering the consequences.
I agreed to join a book club. They're on their 50th novel, and I'm still on the blurb of the first.

The Pleaser's GPS

I have this friend who's such a pleaser, he turns into a human GPS when we're deciding where to eat. I'll be like, I could go for some pizza, and he'll go, Oh, I read your mind! Let's get sushi. I'm convinced he thinks pleaser is short for mind reader. I'm just waiting for the day he hands me a menu and says, You're having the lasagna. Trust me, your taste buds will thank me later.

Pleaser Olympics

I suggested to my overly eager-to-please friend that he should compete in the Pleaser Olympics. He got so excited, he started practicing by agreeing to everything. I asked him, What event are you training for? and he said, The 100-Meter Yes Sprint! I'm thinking of entering too, but in the Skeptic's Marathon. You know, where you doubt everything for 26.2 miles.

Pleaser's Horror Movie

You know you're dealing with a pleaser when you suggest watching a horror movie, and they say, Sure, I love romantic comedies! I'm sitting there, waiting for the jump scares, and they're waiting for the romantic plot twist. It's like watching a horror movie with someone who thinks the scariest thing is a broken heart.

Pleaser's Weather Forecast

I asked my pleaser friend what the weather was like outside, and he said, Well, I heard you like sunny days, so it's sunny. But if you prefer rain, then it's raining. I told him, Just look out the window! He said, I don't want to assume what the window wants.

Pleaser's Got Talent

I told my pleaser friend he should audition for a talent show. He asked, But what's my talent? I said, Saying 'yes' to everything! Imagine the judges' faces when he walks in, and they ask, What's your talent? and he responds with, I don't know, what do you want it to be? I can already see him winning the grand prize: a lifetime supply of indecisiveness.

Pleaser's Coffee Order

My friend, the ultimate pleaser, takes so long to order coffee. The barista will be like, What can I get you? and he'll reply, Oh, I don't know, surprise me! I'm convinced if aliens ever invade Earth, he'll be the one saying, Take me to your leader... or whoever you want, really. I'm not picky.

Pleaser's Pet Peeve

I asked my pleaser friend if he had any pet peeves. He said, Not really, but it bothers me when people don't have a preference. I told him, So your pet peeve is people who don't have pet peeves? He nodded and said, Yeah, it's just so indecisive. The irony was lost on him, but then again, what isn't?

Pleaser's Fortune Cookie

My friend, the eternal pleaser, got a fortune cookie that said, Today, you will meet someone special. He spent the whole day introducing himself to everyone he met, saying, Are you the special one? I guess the fortune didn't specify it wouldn't be a person; it could have been a special sandwich or something.

The Pleaser Dilemma

You ever notice how some people are just relentless pleasers? I mean, they're so eager to please, I'm starting to think they'd say yes to being a human doormat if you asked nicely enough. It's like having a walking, talking yes button. I asked my friend, Are you a pleaser? and he said, Well, if pleasing was an Olympic sport, I'd be a gold medalist. I told him, Dude, the only gold medal you're getting is in the 'Trying Too Hard' category!

Pleaser's Bucket List

My friend, the pleaser, has a bucket list that's just one item long: Make everyone happy. I told him, Dude, even Santa Claus has more realistic goals. Last week, he tried to make a grumpy cat happy. The cat hissed at him, and he said, Well, at least I tried! I'm waiting for the day he tries to negotiate world peace during his lunch break.
If being a pleaser was an Olympic sport, I'd probably win a gold medal for apologizing. I'd like to thank my parents for raising me with guilt and society for setting impossibly high standards. Thank you, thank you.
Being a pleaser must be tough. I mean, how do you decide which person's expectations to meet first? It's like having a to-do list that's longer than your Netflix watchlist.
You know you're a pleaser when you apologize for apologizing. It's like, "Sorry, I'm just so sorry all the time. Wait, did I apologize for saying sorry? Oh, I'm sorry about that too!
I've got a friend who's such a pleaser that they apologize to inanimate objects when they accidentally bump into them. "Sorry, Mr. Door, didn't mean to disrespect your personal space there.
I once dated a pleaser, and let me tell you, every decision was like playing a game of "Guess What I Want." Spoiler alert: I never won.
Ever notice how people pleasers are the only ones who can make a sentence sound like a question even when it's not? "I finished the report on time...? Is that okay...?
You ever notice how the word "pleaser" sounds like someone who's just desperate for approval? Like, "Oh, look at me, I'm such a pleaser! Please like me, please laugh at my jokes, please validate my questionable life choices!
I met someone the other day who introduced themselves as a "people pleaser." I thought, "Great, you can start by pleasing yourself by not telling me your life story in the first five minutes of our conversation.
I tried to teach my cat to be a pleaser, but it turns out she's more of a diva. She just sits there, judging me with those eyes that say, "You can't please me; I'm feline fabulous!
I recently discovered that my pet dog is a pleaser. I mean, he wags his tail so much, it's like he's auditioning for a role in a Broadway musical. "Coming this fall, starring Fido the Pleaser in 'Tails of Approval!'

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