'Things started to get really awkward': Guy accidentally invites boss to weekend getaway with friends, boss shows up

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Ben Weiss • Writer and Editor
Mar 6, 2023 2:00 PM EST

This guy discovered that he accidentally invited his boss to his weekend getaway with his friends. Sounds like this boss was lonely and/or couldn't take a hint; that being said, it seems like he handled the weekend as well as he could. The employee who messed up shared this now updated thread on Reddit's r/tifu subreddit.

 

The highlight of the weekend definitely came when the Redditor's friend started cracking inappropriate jokes after the group had been drinking. The Redditor got anxious and didn't know how to compose himself in front of his boss, but his boss apparently chimed in and contributed more dirty jokes. This certainly will change the tone for what the office dynamic will look like come Monday morning, but the truth is, work is work, and outside of work is a totally different ballgame. People were a bit tough on the Redditor in the comments for getting uptight. It definitely is a stressful, awkward situation, but maybe next time it won't be.

 

Keep scrolling below for the full story. For more, here's one about an employee who discovered their CEO is their half-brother.

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  • 01
    World - "TIFU By Accidentally Inviting My Boss to My Weekend Getaway"
    via Mike Erskine
  • 02
    Font - TIFU by Accidentally Inviting My Boss to My Weekend Getaway S So, I had been planning this weekend getaway with my buddies for months. We were going to a remote cabin in the woods to have some fun, drink some beers, and forget about work for a while. As the weekend approached, I was excited to finally take a break from my stressful job and just let loose.
    via u/neon_gaber
  • 03
    Font - But here's where I messed up: I accidentally included my boss in the group message about the weekend getaway. I didn't realize it until I saw his response in the chat, saying he was excited to join us. I immediately panicked because, let's be real, nobody wants to spend a weekend away with their boss.
    via u/neon_gaber
  • 04
    Font - I tried to backtrack and come up with some excuse, but it was too late. My boss had already made plans to come with us, and there was no way out of it. So I spent the whole weekend trying to have fun while also keeping a professional demeanor around my boss. It was the most awkward and uncomfortable weekend of my life.
    via u/neon_gaber
  • 05
    Font - TL;DR: Planned a weekend getaway with friends. Accidentally included boss in group message, couldn't back out. Spent weekend awkwardly balancing fun and professionalism. Edit: For anyone wondering how the weekend getaway was. I posted an update!
    via u/neon_gaber
  • 06
    Font - TIFUpdate By Accidentally Inviting My Boss to My Weekend Getaway M Wow, I never expected my last post about accidentally inviting my boss to my weekend getaway to blow up like that! Thank you so much for all the comments and messages, and for those who asked for an update, here it is. And for some who did not understand, the weekend already happened.
    via u/neon_gaber
  • 07
    Font - First things first, it was just as awkward as you can imagine. I spent the entire weekend trying to have fun with my friends while also trying to impress my boss. I felt like I was constantly walking on eggshells, trying not to say or do anything that would make me look bad in front of him.
    via u/neon_gaber
  • 08
    Font - But despite the awkwardness, we did have some fun moments. We went fishing, we played board games, and we even went on a hike in the woods. I tried my best to act normal around my boss, but I could tell he was a bit uncomfortable too.
    via u/neon_gaber
  • 09
    Font - At one point, my buddy brought out a case of beer and we all started drinking. My boss joined in too, and before I knew it, we were all pretty drunk. That's when things started to get really awkward.
    via u/neon_gaber
  • 10
    Font - One of my friends, let's call him Dave, started telling some inappropriate jokes. I knew I should have told him to stop, but I was too afraid of offending my boss. So I just sat there, trying to laugh politely while Dave told joke after joke.
    via u/neon_gaber
  • 11
    Font - Then, to make things even worse, my boss started telling his own inappropriate jokes. I couldn't believe it - this was my boss, the guy who signs my paychecks, telling dirty jokes in the middle of the woods.
    via u/neon_gaber
  • 12
    Font - The rest of the weekend was pretty uneventful. We all went to bed early each night, and I made sure to keep my distance from my boss. I could tell he was relieved to go back to work on Monday, and so was I.
    via u/neon_gaber
  • 13
    Font - Overall, it was a pretty stressful and awkward weekend. But at least I learned a valuable lesson - always double-check who you're inviting before you hit send. And maybe, just maybe, don't invite your boss to your weekend getaway in the first place.
    via u/neon_gaber
  • 14
    Font - TL;DR My boss came to my weekend getaway with my friends, making it awkward for me to act normal around him. things got really uncomfortable when everyone got drunk and started telling inappropriate jokes.
    via u/neon_gaber
  • 15
    Font - AnoxisD 2 days ago Hey mate, the fact your boss cracked 'inappropriate' jobs is a good sign. It means there is a degree of trust between you. In a previous job, my boss was my best mate, seriously couldn't ask for more. Yes, we had our serious moments typically where I got a bollocking because I forgot to do something big, but we also had our far less serious moments - sitting in a control room at 10pm laughing our off at something seriously not worth the laughter. Now we've both moved on
    via u/neon_gaber
  • 16
    Font - Jag0tun3s 2 days ago You should've tried to ignore that he is ur boss. The only way, in my opinion, to kill the awkwardness 792 Reply Share
    via u/neon_gaber
  • 17
    Font - ldnk +2 2 days ago The only TIFU I'm seeing here is that your own anxieties/insecurities prevented you from having fun. 476 Reply Share
    via u/neon_gaber
  • 18
    Font - silent_cat 2 days ago Seriously, you tried to impress your boss outside of work? Screw that. At work I get paid. Outside of work I'll treat him like anyone else. 313 Reply Share
    via u/neon_gaber
  • 19
    Font - Zikkan1 2 days ago If your boss accepted the invite then this was a perfect opportunity for you to become buddies with your boss, which never hurts. 219 Reply Share
    via u/neon_gaber
  • 20
    Font - 111210111213. 2 days ago You put your boss way too high up on a pedestal. 4 199 Reply Share
    via u/neon_gaber
  • 21
    Font - garry4321 2 days ago So let me get this straight; Your boss came along and meshed well with your group, didnt take it so seriously and even told some jokes? You seem like a prude NGL. Your boss is human too. Why cant you just treat them like a person?
    via u/neon_gaber
  • 22
    Font - neon_gaber OP 2 days ago I never was on a getaway with my boss. At work, he always behaved more seriously. I wasn't expecting him to act like that, it made me panic, but after reading all the comments, I realized there wasn't actually a reason to panic
    via u/neon_gaber

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