TIFU by accidentally sexting my boss instead of my boyfriend

r/

Kill me.

So I’ve been dating my boyfriend for a while and we’ve been sending flirtier texts lately. Yesterday, he sent something flirty and I decided to one-up him. Nothing graphic, but I replied with: “If you don’t behave, I’m gonna have to punish you tonight 😏💦.”

Only I didn’t send it to him.

I sent it to my boss.

My 58-year-old, married, very Catholic boss who ends every meeting with “Let’s all be kind to each other.”

The realization didn’t hit until he replied with, “I’m assuming this wasn’t for me.” I died. I wanted to throw my phone across the freeway. I immediately apologized, said it was a mistake, and to his credit, he was very professional and said not to worry, “these things happen.”

But now I can never say the word “punish” again. Ever. Anywhere. Not even in board games.

TL;DR: Tried to sext my boyfriend, accidentally sexted my boss. I’m never going to work again.

Comments

  1. _aaronroni_ Avatar

    Hey, at least that’s pretty mild and not like a pic of something you’d REALLY not want him to see

  2. Expensive_Top_796 Avatar

    🤣🤣 just another day in the life. 🤣🤣

  3. DMonpoke Avatar

    This is a thing in our current age of being easily connected across technology. Many of us are bound to do it and many of us have. He played it off perfectly; it happens, it wasn’t meant for me, let’s move on. You’re lucky it happened with a boss who understands. You goofed. But it’s not a fuck up.

  4. morbidi Avatar

    Now you can use the marvelous world of synonyms :

    https://www.merriam-webster.com/dictionary/punish PUNISH Definition & Meaning – Merriam-Webster

  5. highandhungover Avatar

    An incredibly real story that is not AI, finally

  6. lyfe_Wast3d Avatar

    Hi I’m boss

  7. hippieninja6 Avatar

    It’ll be ok😅 we all fuck up the recipient sometimes😅 at least the boss understands and is cool… that’s the rare part… have good day

  8. LaraNeedsMore Avatar

    Oof, that’s a legendary slip-up, your phone really said “career challenge unlocked.” At least your boss handled it like a pro! Just embrace the cringe, laugh it off, and maybe rename him in your contacts to avoid a sequel.

  9. Coiltoilandtrouble Avatar

    Eh your boss was a champ about it. Just forget about it

  10. worldofcrap80 Avatar

    Literally the name of a podcast

  11. Heartless-otaku07 Avatar

    Better your boss than your dad , I was txting my bf as a teenager late like that and said me and the twins miss you and accidentally hit dad instead of Dan . Thankfully I was able to delete it/ unsend though before he saw as he was asleep

  12. PerspectiveJohn Avatar

    20+ years ago, my stepsister took a very naughty photo of a soda-pop can in an extra secret place to send to her husband. Instead of sending it to her husband, she sent it to her father. It was a special kind of Christmas that year.

  13. NovaDusk12 Avatar

    Honestly? This is the kind of story that’s going to haunt you for years but also absolutely kill in a group chat one day. At least your boss didn’t respond with “😏💦.” Small mercies.

  14. Babblingbutcher420 Avatar

    Honestly if it’s just a text like that I think it creates a fun awkwardness in the work place. You’re lucky you didn’t send a pic.
    Hey and just because he’s a catholic doesn’t mean he wasn’t freaky deaky in his youth. That man probably did his fair share of “punishing” and then found god 😂

  15. kidsaredead Avatar

    how do you reply to someone else from a private conversation ?

  16. assassbaby Avatar

    the problem is you dont have a separate work phone.

    my personal does not have any work people contacts

  17. BananaBrute Avatar

    Now you know when your boss says lets all be kind to eqch other, he means that for real!!

  18. Raingood Avatar

    “Let’s all be kind to each other.” – Does he mean one on one or all at the same time? What a perv! Def needs to be punished.

  19. sen456 Avatar

    would never even have my boss’ number to text. unless it was like a young friend boss. my company uses slack and even there im always anxious about accidentally sharing to it

  20. _nosynose_ Avatar

    22 day old account and this is the only post. If you factor in the fact that this follows the same pattern as all those other « TIFU by sexting my X instead of Y », I’m tempted to argue that it’s ChatGPT doing the lifting here.

  21. jungle21 Avatar

    I recall a friend of mine from football who accidentally sent a photo to our head coach instead of his girlfriend.

    He went to the solarium and sent a picture of himself naked only covering his noble parts with a sock. He was embarrassed 😅.

  22. The_Darkness140 Avatar

    At least it wasn’t a spicy photo. THAT would’ve made things awkward, probably would’ve gotten you a promotion though. 🤔

  23. jugo5 Avatar

    My one employee used to text me instead of his wife. He’d send one that says “love you baby 😘” then followed by “Oops sorry”. I always laughed.

  24. Kynandra Avatar

    There are a lot of people in this sub that text their boss naughty things instead of their BF/GF/Husband/Wife.

  25. Mehnard Avatar

    So, Did you get a raise?

  26. viper3k Avatar

    I hope he responded “let’s all be kind to each other now”

  27. lookaroundewe Avatar

    Skip to Halloween and your boss dresses as the Punisher.

  28. rdmvdb Avatar

    I texted my boss “I love you” one night. Didn’t realize it until the next morning when I texted my girlfriend (what I thought) again. He didn’t respond. I ended up going into his office saying “look it’s not that I don’t love you but that text I sent was meant for someone else’ . He thought it was hilarious and we both laughed (him a little harder than me).

  29. ATrollOfTheDice Avatar

    It could be worse. I sent a flirty text to my mother once. She didn’t understand, so she showed it to my brother who was visiting her at the time. So not only did I feel utterly ashamed, I have a brother to remind me every now and then for the rest of my life.

  30. jordanpatriots Avatar

    Oh, another “accident” to someone’s boss. Congrats on the promotion lol

  31. bucho80 Avatar

    meh, lean it to it with your boss, something like “Hey, I need next Thursday off or you get the punishment again!”

  32. Thin_Performance7344 Avatar

    It’s almost like it wouldn’t of happened if you would have been doing something productive with your time.

  33. hippykid64 Avatar

    I once accidentally sent my boss a message meant for my son about leftovers in the fridge…he answered as if he were my son…to see how long it would take me to notice my mistake. He was a real piece of work!

  34. brakeb Avatar

    I don’t even have my manager contact info on my phone

    Perhaps move the interactions with work people to a different message system or move your boyfriend to signal or WhatsApp?

  35. wolfhuntra Avatar

    Things happen. Don’t punish yourself over it 🙂

  36. AngelsMagicdust Avatar

    Blame a friend. They had your phone and asked your boss’ name whilst they were playing a game on your phone and you were distracted in that moment so just told them his name. They did it as a joke.

  37. Shadowdragon409 Avatar

    What boardgame would you say “punish” for?

    Also, that title made me think you were sexting your boss for weeks or months on end. Not a single text lol.

  38. tweakingforjesus Avatar

    A client once sent a very flirty text message that was clearly not meant for me. She immediately apologized saying that was meant for her husband. I laughed my ass off.

  39. Ecstatic_North_7367 Avatar

    As a manager that has seen & heard it all. Your good. Shit happens.

  40. Boniouk84 Avatar

    Congrats on your promotion

  41. AshkenaziTwink Avatar

    girl you didn’t just burn a bridge, you set the whole office on fire 💀 “Let’s all be kind” is now loaded forever

  42. SkarbOna Avatar

    Shit I have some fat contacts in my private phone…hope it doesn’t ever happen lol.

  43. RedNeckPizzaMan Avatar

    Ok sorry but I gotta do this or I’m gonna burst.

    Buh ha ha ha ha ha ha. Breathe. Buha ha ha ha ha.

    My wife did this to her boss once.

  44. ethanlewis12 Avatar

    Considering he said “these things happen”, I’m now curious whether this has happened to him a few times before

  45. hjo1210 Avatar

    My husband sent his boss a very detailed description of what he was going to do to me when he got home. His boss replied “I’m hoping this was for your wife.” Hubby almost died of embarrassment almost – my husband always checks who he’s replying to now though.

  46. rncshow Avatar

    Hey, on the upside when you get fired in a few weeks due to the awkwardness, you at least know why

  47. Travice0 Avatar

    My old boss Ted was a real one.

    I accidentally sent him an “i love you babe” over IM that was meant for my girlfriend.

    He responded back with “awww i love the work you do too” as i heard him laughing like a madman from his office.

    We never spoke of it or mentioned it again after that.

  48. OrionTuba Avatar

    I swear this followed the exact same template of 4 other miss texts I’ve seen here

  49. gwillacker Avatar

    Stop texting while on the freeway, including reading texts.

  50. steen101984 Avatar

    Just wait until he punishes you Monday morning.

  51. SadDragonfruit6181 Avatar

    I’m going to punish whoever got ahold of my phone and sent that. Sorry.

  52. Kind_Blackberry3911 Avatar

    This reminds of a time when our whole team was in an online meeting, while WFH, and I forgot my mic was on. We were watching a training video as a group. The presenter said something and I muttered, “All the fucking time” to myself… or so I thought. Immediately my chat lit up: “YOUR MIC IS ON!!!” Including from a real bitchy woman on my team who I do not trust one iota.

    I was mortified. My manager is a WWJD bracelet-wearing, super-Christian pure-as-the-driven-snow Certified Nice Guy and he’s probably never even watched a movie or TV show with cussing, let alone dropped an F-bomb.

    I was so embarrassed I never said a word to my manager, and bless his heart, he said nothing about it, either. I did immediately apologize to the three people who had chatted me. Thankfully this incident had no repercussions but by golly I’m more careful with my mic these days!

  53. Red_dragon23 Avatar

    If I was your boss one day in the future at the right time I would say “You’re not going to punish me are you? 😉

  54. Speechisanexperiment Avatar

    I send my wife sexy texts all the time followed by “sorry, that was meant for my boss.”

  55. Ag_in_TX Avatar

    I am a 63 year old very Catholic boss. I got a similar text from one of my 20-something year old female engineers. It was the funniest thing I’ve had happen in years.

    She was mortified – I thought it was hilarious.

  56. snarknsuch Avatar

    My boss was named Chris, and my bestie I talked shit about him with was named Christine in my phone.

    I had to change her to Xtine after a few too many close calls.

  57. Otherwise_Yellow_311 Avatar

    I wish I could’ve sexted my boss. Him and his rules ugh

  58. RaiseYourDongersOP Avatar

    new promotion incoming