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Man accidentally mixes up his envelopes and confesses his love to his boss.

Man accidentally mixes up his envelopes and confesses his love to his boss.


"TIFU by Accidentally Sending a Love Letter to My Boss Instead of My Girlfriend"


So, this literally happened yesterday, and I’m still cringing at the thought of going back to work on Monday.

A bit of context: I’ve been dating my girlfriend for about six months now, and things have been going great.

We’re both a bit old-fashioned, so we like sending each other handwritten letters every now and then, just to keep the romance alive, you know? Anyway, I spent the better part of Sunday evening crafting the perfect love letter.

I’m talking about pouring my heart and soul onto this piece of paper, confessing my deepest feelings, and even including a couple of (what I thought were) pretty steamy paragraphs. I sealed it in an envelope, ready to be mailed first thing in the morning.

Monday morning comes, and I’m in a bit of a rush. I grab the letter from my desk, along with a bunch of documents that I needed to hand over to my boss. My mind’s already on the busy day ahead, so I’m not paying much attention to what I’m doing.

Fast forward to the afternoon, my boss calls me into his office with a very… interesting look on his face. He hands me an envelope – the envelope – and asks if I meant to give this to him. My heart sank. I immediately realized what had happened. In my morning rush, I’d mixed up the envelopes and handed him my love letter instead of the documents.

Thankfully, my boss is a pretty cool guy. He laughed it off, saying he was flattered but happily married. He even joked about my “impressive” choice of adjectives. I wanted to disappear right then and there.

So yeah, that’s how I ended up accidentally confessing my undying love to my boss instead of my girlfriend. I’ve since rewritten the letter (and triple-checked the recipient this time). As for my girlfriend, she found the whole ordeal hilarious once the initial mortification wore off.

Here were the top rated comments from readers:


"My dearest June, it's been a fortnight since I last gazed upon your ample bosom..."


...talking like that should automatically get someone a 30% raise.


"As for my girlfriend, she thought my TPS reports were really boring. In fact, she was baffled as to why I would have given her an envelope full of TPS reports at all."


-I want to talk to you about something
-Is it about the love letter I gave you accidentally?
-*stops pouring 2 glasses of wine*. Accidentally?


The worst part is that it looks like you did that in office time, since you gave it with the other documents (even though you really did it at home).


At least your love letters didn't get posted in a literal book of the Bible 😂😅 Seriously though, this would make my stomach turn for weeks at least.


Yea I’m going to need you to come in on Saturday.


Well... what did it say!!?

So, yikes, right? Luckily it sounds like it worked out okay...hopefully? Does anyone have an embarrassing work mistake that can top this one?

Sources: Reddit
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