Supervisor tries bonding with younger staff, ends up exposed for gossiping after intern sends message to the wrong person: 'Happy to report that I’ve now transitioned to a different department'

Author image for Isabella Penn
Isabella Penn
Dec 9, 2025 7:00 AM EST

Working for a company with a small team can feel a bit like working on a group project you can't escape. Everyone's close, everyone's tired, and everyone's pretending they don't hear each other's Slack notifications. At my last job, we all ate lunch together every day because "that's our culture," which mostly meant performative small talk and pretending we were all best friends. When a company is tiny, the walls feel even tighter, and the pressure to bond (especially with management) gets heavy fast.

And the truth is, as fun as it can be to vent about shared suffering or the coworker who loudly takes credit for breathing, you never really know who's listening. Or in this case, who's watching.

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  • That’s what happened at this startup, where a new employee noticed her supervisor, Tom, keeping a private chat with an intern pinned on his monitor during training. They often gossiped about coworkers, so it wasn’t shocking to learn she wasn’t an exception. 

    One day, after Tom accidentally addressed her instead of the intern, a message from the intern popped up on her screen: “She was SO offended.”

    She wasn’t offended, but she was done with the high-school level drama. She moved to a new department, Tom stayed awkward, and the intern couldn’t even make eye contact. 

    Sometimes the best revenge is simply outlasting the weirdos.

  • Safari File Edit View History Bookmarks **!: slack Why Slack? Solutio
    via Stephen Phillips - Hostreviews.co.uk For Unsplash+

  • "Gossipy coworker sends a 'private' message about me to me"

    When I started my current job, two things became very apparent to me. One, my team was small, given that the company itself is not much bigger than a startup.
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  • The team is also fairly young, as the CEO has admitted they're the ones who care the most about their work.
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  • We'll call my supervisor Tom, a man in his thirties who interviewed, trained, and worked closely with me.
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  • We'll call the intern Jane, a woman in her early twenties. I knew they were close.
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  • Again, the team is young, and a lot of young women including myself have been getting hired recently.
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  • These two talk a lot about their lives, which is fine and normal. But they also gossip a lot about other coworkers and Tom comes off like he really REALLY wants to bond with us young people.
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  • Once they realized I wasn't joining in, they kept it to private chats. I know this because I sat next to Tom and saw him on his monitor, clear as day.
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  • Couldn't help it. While demonstrating something to me during training, I noticed he'd pinned their channel of private messages.
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  • I don't know what I expected. I knew I wouldn't be an exception. Of course, I'm going to walk by to see Tom's chats on his monitor like always (unrelated, I have an ongoing list of grievances for this guy) and of course. I see my name.
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  • Of course. Then one day, we come back from a meeting and Tom asks me if I can come into the office tomorrow.
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  • I come in everyday and so does he. He knows this. Then Jane answers his question and I realize he was talking to her.
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  • No biggie. Whatever. Tom apologizes for addressing me by accident, I laugh, I get back to work.
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  • A notification pops up in the corner of my laptop screen. It's a message from Jane.
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  • person using phone and laptop
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  • "Lmao she was so SOOO offended you called me OP." It vanishes two seconds later. I laugh again and say "oh, I'm not offended.
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  • Don't worry, I was just confused." Meanwhile Jane can't get away from me fast enough. Meanwhile I'm trying not to burst out laughing.
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  • Happy to report that I've now transitioned to a different department and while Tom is still annoying, Jane will barely look me in the eye.
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  • Seriously, on one of our last days together, we were alone in the office and didn't say a word to each other, not even good morning.
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  • HellBunny69 Ahhh this reminds me of a time I was in the office and had my back to a couple coworkers who thought I couldnt hear them because I had my headphones in. Little did they know I hadn't actually picked my playlist yet so I heard all the shit they were chatting right behind me. So I just casually responded to one of their comments and added "I hear everything you know">
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  • OP Immediate-Evening Honestly, I've wanted to do this several times but held back for the sake of keeping my head down and working. I commend your bravery
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  • rbad8717 Are all 3 of you all named Jane? How da hell can they message the wrong person especially if they already have chat history
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  • OP Immediate-Evening My guess is that I was at the top of her chat history because she'd sent something to me recently? Otherwise, she just had my name on her mind and just....made a mistake
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  • cardamomgrrl I once sent theee worst pic of me ever - waking up on an airplane - to the guy who'd interviewed me a few days before rather than to my bf because of the chat order. Humiliated. Got the job tho.
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  • OP Immediate-Evening Hahahaha that's amazing!
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  • Ok-Cat-4975 I had a job as a consultant to help doctor's offices meet the requirements to get a government incentive (electronic health records). I was helping an office remotely so one person was sharing their screen while another was also on the video call. They had a chat open that they thought was on the other screen but I could see their messages. She's so annoying, why do we have to do this? type messages. I calmly told them that I can see their chat and that I'm not making these rules, I'
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  • halcyonwade My brother once got fired from a (very good) job for accidentally sending a text saying a slur about a colleague to that colleague. Yes, my brother is an asshole. And yes, he was sure he was wronged somehow.
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  • CharlieBr87 the front desk I did this once girl was VERY close to a young man on my team. I also had a friend whose name stayed with the same letter. One morning I sent my friend a message like "oh she gets his lunch like all the time, like they must be hooking up" I got a message back on teams: "why would you send this to me?" I responded out of sheer embarrassment "because I'm an asshole..."
    via CharlieBr87
  • cavia_porcellus 1972 I was covering a colleague for her break. When she got back and I got back to my desk I see my phone ringing from her desk. The desk I was just at. I answer it all happy "Hellooooo!" And she proceeds to talk sh!t about me and I realize about three sentences in she dialed the wrong number and thought she was calling her work bestie at a different extension. When she finally finished her diatribe I said "This IS cavia, thanks so much for that" and slammed the phone down. Prior
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  • LibraryLuLu I've had one of my staff members sending a text message complaining about a manager to that manager. It happens. Also, he's an idiot.
    via LibraryLuLu
  • 000-f I had this happen to me, but it was 100% an on purpose mean girl tactical move. Even a "whoops, teehee" message afterwards
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  • Chemical-Pattern480 At my last job, my Manager sent a Slack to me that she meant to send to another Manager, talking crap about me. I screen shot it immediately and replied with, "I don't think you meant this to go to me?" And she tried to play it off that she did. It was her 3rd HR violation in 9 months, but other than a formal apology, nothing happened. She was a big reason why I left.
    via Chemical-Pattern480

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