Boss dates secretary and fast-tracks her promotion into power, sidelining his longest-serving worker’s career: ‘My career has stagnated while she gets all the good projects’

Author image for Etai Eshet
Etai Eshet • Editor
Dec 2, 2025 9:00 AM EST

Call me old-fashioned, or archaic, but I need to keep the people in my life firmly within their respective categories. Call me a categorizer.
So this story makes me uncomfortable on about four different levels. Office romance is already messy, but this one comes wrapped in a power imbalance, workplace favoritism, and a side of unpaid emotional labor.

Boss hires a secretary, starts acting like the office is a bar with fluorescent lighting, and before long, the whole place is watching late-night drinks, visible love bites, and affection-showing sessions in the same space where people sort orders. When staff raise concerns, the response is not to clean things up, it is to quietly fire half the team and promote the secretary to running operations.

The newly promoted favorite starts shifting attention to a coworker who has already been told there is nothing going on between her and the boss. Lines blur, a few more affection-showing sessions happen, feelings get tangled, and then the ladder suddenly looks a lot steeper. Raises only come after threats to quit. Extra responsibilities come with no real training. Meanwhile, the woman who walked in as support staff now gets overtime to sit and chat with leadership, first pick of good projects, and zero pressure to help when things fall behind.

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  • Boss Dating Secretary

    A man and woman sit at a desk holding hands flirtatiously in an office while a coworker looks over with suspicion.
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    Image is representative only and does not depict the actual subjects of the story.

  • Boss hired a secretary about 2 years ago and immediately there was some unprofessional behavior going on that we all noticed.
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  • They would drink and hang out late at the office.. people saw inappropriate touching, making out, and hickey marks.
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  • it bothered everybody and I was tasked with bringing it up to the boss since I was friendly with him.
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  • He ended up firing half the squad and promoted her to oversee the whole operations in a span of 3 months.
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  • Things settled down and she quit drinking. She started flirting with me heavy and since the boss told me they werent involved, I got carried away myself and made out with her a few times.
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  • A man and woman sit at a desk holding hands flirtatiously in an office while a coworker looks over with suspicion. You said: ChatGPT said: A man and woman flirt openly while holding hands in the office, as two coworkers in the background watch with concern and clear disapproval.
    via Ground Picture

    Image is representative only and does not depict the actual subjects of the story.

  • Yea I fcked that up but I thought she could be the one. It didnt work out and weve had a bad relationship with one another because I had to work my way up and ask for raises.
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  • threatened with quitting the job in order to get higher pay. everything was handed to her.
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  • She would always complain that we are behind on orders, but never come around to help us out.
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  • always just constantly flirting with the boss. She gets paid overtime just to hang out and talk with the boss after her 8 hours Well nowadays, im noticing the boss and her are getting extra close again and hanging out after work.
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  • Leaving in the same car together. He use to go to the gym after work but now does it before work to hang out with her more.
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  • He's acting extra happy too, its weird because he wasnt like this before. My career has stagnated while she gets all the good projects.
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  • A woman leans in with a flirtatious smile while discussing documents with a male coworker, creating an intimate moment in an otherwise busy, professional office.
    via Ground Picture

    Image is representative only and does not depict the actual subjects of the story.

  • im paid a decent wage, 7 above minimum and im an unskilled worker so im kind of stuck.
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  • Im stuck doing menial tasks and im rarely taught to new things. Ive been here the longest.
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  • How would you approach the situation? would you bring it up with the boss?
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  • Ive already done so and I felt like they don't take me seriously. But whenever she asks them for something, they will drop whatever for her.
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  • I want to quit but the job market is getting tough I hear. Tough love advice welcomed, just be gentle
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  • There is no clever way to fix a culture that runs on favoritism and blurred boundaries. The realistic advice here is simple and harsh. Quietly update the resume, and look for a place where your CV and Dating App bio are not one and the same, rather than trying to compete with a relationship that already owns the room.

  • TryharderJB You should have done what the secretary did instead of doing it with the secretary.
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  • OP poolboypedro2323 bang & flirt with the boss? loli dont roll that way but solid advice nonetheless
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  • TryharderJB lol glad you took it the way intended. In seriousness, nothing good will come your way if you bring it up with the boss. If you can, update your resume, brush up any skills you need to learn or sharpen and start looking for a new job. Here's the tough love bit: only you can change your situation so get going. Nobody will give you time so you just need to take it wherever you can and do the things that need to be done so you can move on asap.
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  • OP poolboypedro2323 I already had brought it up before the first time they were acting up, and he still kept me because I was in charge of one of side businesses that is now defunct. I think this time would be different since im more expendable. its just that other jobs are paying less right now then what I have. & I did some dumb things in my past so thats what holds me back good news is their retail store is suppose to open in a couple weeks and im going to be running it. they are going have a
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  • Square-Emergency-531 At a larger corp, hr would be unusually helpful for this. The big corps seem to actually care about boss/ underling relationships for legal reasons. Other than that, if your boss shows their colors this way you really do need to find a way to leave. Mostly trying to get accountability for your own bosses misdeeds will backfire, with few exceptions.
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  • OP poolboypedro2323 its a small operation with about 5 of us in office with the 2 brothers that started the business and the rest being online support. Ive brought up her being favored several times in front of both the bosses and secretary herself, and im still here for some weird reason their retail store which i will help run should be opening up in a couple of weeks and ill be away from them two canoodling hopefully. i wished the other brother saw how this could be a bad thing but he seems t
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  • Fabulous_Computer965 You knew she was a hoe but thought she was the one? I'm confused. This woman is a professional manipulator, she must be attractive and has never been shut down. Stay far away. Maybe you should get out of this circus and find a new job.
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  • OP poolboypedro2323 I confronted the boss about whether the rumors were true and I took his word for it. He even said, "you can have her".. then she started coming onto me and I fell for the trap. quickly realized the manipulation tactics she would pull and left the relationship to die out. when she first came in, she wasnt attractive. no father figure in her life, so she has a hatred for men. she use to be overweight, but she lost a lot of weight so shes def feeling herself. and she dresses up
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  • Bababababababaa123 It's good to be the boss!
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  • OP poolboypedro2323 you ain't lying! im trying to be more happy for him than jealous because we use to be tight and i do appreciate him supporting me when I started. i just wish he never hired that chicken lol ive been trying to become my own boss lately, reading up and trying ideas. that way we dont have to answer to nobody!
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  • Bababababababaa123 My comment was a riff from an old Mel Brooks movie haha!
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  • OP poolboypedro2323 haha I was getting all introspective and deep, but it aint that serious !! just live the best you can I remind myself
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  • Direct_Sir_2012 kinda wild how that works, society's just messed up like that
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  • marshmellowyoda Join in on the fun!
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  • !gif shecho18 Following this post for such "juicy" drama.
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  • RoRoo1977 Leave
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management terrible coworkers workplace discussion employment issues boss workplace-stories hr manager bosses work coworkers colleague PTO managers supervisor workplace Horrible Bosses work-life balance
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