Funny Prank Letters

(280+ words)

Dear [Name],

I hope this letter finds you… Oh wait, you’re not here yet. Surprise surprise!… It’s like your watch is set to a different time zone or you’re on a mission… However, I do have a few suggestions that might help you improve your punctuality game. First, try setting your alarm a little earlier. It’s a radical idea… we can’t wait to see you bright and early (or at least, not too late) tomorrow.

Sincerely,

Everyone

(260+ words)

Dear [Annoying Coworker],

I hope this letter finds you well, although I suspect it won’t since you seem to always be in a foul mood. Maybe it’s because you wake up on the wrong side of the bed every day, or maybe it’s because you have a permanent wedgie… But fear not, for I have a solution that just might solve all our problems. How about you take a vacation? A nice, long one. Say, six months or so?… maybe a little time off will do wonders for your mood and you’ll come back to work as a changed person.

Sincerely,

Everyone

(280+ words + includes a stick of gum)

Dear [Name],

I hope this letter finds you well, and I hope you don’t mind if I get a little personal here. You see, I couldn’t help but notice that your breath smells like a hot garbage dump… But fear not, my friend! I have a few solutions that might help you combat this stinky problem. First… And hey, if all else fails, maybe you can embrace your bad breath and start a new trend. Who knows, maybe stinky breath will be the next big thing.

Sincerely,

Everyone

(218+ words)

Dear [Bad Haircut],

I hope this letter finds you well, even though I can’t help but notice that your hair seems to have taken on a life of its own…And let’s talk about that fringe situation. It’s like a wall of hair blocking your forehead, almost as if you’re trying… eventually, or at least find a job as a scarecrow. Either way, I’ll be here to support you (and your hair) through it all.

Sincerely,

Everyone

(270+ words)

Dear [Bad Taste in Men],

I hope you’re doing well and that you’re ready for some tough love. You know, like when your best friend tells you that you have spinach in your teeth and you want… I’m not trying to be mean or anything, but let’s be real. The last guy you dated was so unreliable that he made the weather look consistent… Anyway, thanks for listening to my rant. I hope you don’t hate me too much, and that you find the perfect guy (or cat) someday.

Sincerely,

Someone Who Cares

(225+ words)

Dear [Body Odor],

I hope you’re doing well, but I can’t help but notice that there seems to be a bit of a funk following you around lately… Now, I’m not saying you need to start bathing in perfume, but maybe consider taking a few extra minutes in the shower and… In all seriousness, though, I do care about you and I don’t want your body odor to affect your relationships… Thanks for taking the time to read this letter, and I hope we can work together to keep things smelling fresh.

Sincerely,

Someone Who Cares

(245+ words)

Dear [Name],

I hope this letter finds you well, although I suspect it won’t because karma has a funny way of catching up with people who do… I mean, who needs trust and honesty when they can have deceit and betrayal… But don’t worry, I’m not mad. I actually find your lack of integrity quite amusing. It’s like watching… In all seriousness, I just wanted to let you know that even though you’re a cheating scumbag, I still wish you the best (kind of)…

Sincerely,

[Your Ex Who Deserves Better]

(205+ words)

Dear [Name],

I hope this letter finds you well, but judging by your recent behavior, I suspect it probably won’t. I mean, who knew being… while you were busy playing “two truths and a lie” with me and your other partner(s), I was busy playing “two middle fingers and a goodbye”…don’t worry, I’m not mad. In fact, I find your cheating antics quite comical… may your future partners be able to keep up with your web of lies.

Sincerely,

[Your Ex Who Deserves Better]

(265+ words)

Dear [Name],

I hope this letter finds you well, and by the time you finish reading it, I hope to have given you quite the shock. Are you sitting down? Good, because… Okay, here it goes… I’m pregnant! I know, I know, it’s a shocker. I couldn’t believe it myself when… I hope you’re as thrilled as I am. But then again, maybe you’re not. Maybe you’re thinking… a terrible prank to play on someone. But I couldn’t resist. I’m sure you’ll forgive me eventually… You’re truly one of a kind, and I’m grateful to have you in my life.

Sincerely,

[Name]

And again, I’m not pregnant.

(235+ Words + Fake winning lottery ticket included.)

Dear [Name],

I hope this letter finds you well and not too annoyed at receiving a random lottery ticket from me… you’re thinking: “Great, now I have to waste my time scratching off this thing just to find out that I didn’t win anything… I had a dream last night that you won the lottery and bought me a yacht. And let me tell you, it was a really nice yacht. It had a hot tub, a built-in bar, and… Maybe you’ll win big and we can split the winnings 50/50 (or you can… scratch away and let’s hope that dream of mine becomes a reality. And if not, well, there’s always the option to sell a kidney on the black market.

Sincerely,

[Your Name]

(230+ words)

Dear [Name],

I hope this letter finds you in good health and not hovering over your employees like a vulture waiting to pounce on any mistake… with a spoonful of sugar instead of vinegar. You know, like Mary Poppins taught us… Jokes aside, I do want to address the fact that your behavior has been affecting the morale and productivity of the team. It’s hard to focus… Thank you for your attention to this matter, and I hope to see a kinder and gentler version of you soon.

Sincerely,

Everyone