57-year-old Executive assistant catches her boss getting cozy with a young woman from logistics, lies when his wife asks if anything abnormal is happening, deciding silence is safer than risking her job

Author image for Etai Eshet
Etai Eshet • Editor
Aug 14, 2026 7:15 AM EDT

Office affairs play out like a daytime soap opera written by someone who has never met a subtle person. The boss, the young woman, the wife asking questions, the assistant caught in the middle. Everyone is playing a role in the drama, and the script is painfully obvious

A 27-year-old from logistics decides the director is her new main character. She ignores the chain of command like it is a suggestion box. She makes his coffee before the actual assistant can get there. She books his trips. She brings homemade desserts. She brags about lunch dates outside the office like she is collecting achievements. The boss entertains it because having a personal fan club is apparently part of the job description now.

The only unexpected, and also great, part of this is that this woman asked r/whatdoIdo and pretty much immediately decided what's right for her.

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  • My boss's wife wants me to tell her if I saw anything abnormal at the office. I said I didn't, but I lied and it involves a young woman

    Blonde woman in a blue blouse sits at an office desk, looking to the side beside a keyboard and papers.
    via PeopleImages

    Office worker in her 50s looking conflicted at her desk

    Image for illustrative purposes.

  • I (57F) work as an executive assistant for the director (47M). Our relationship is good, I get along with everyone(there are round 500 people here) and I am like an auntie for my colleagues.
    via Working-Simple8753
  • There is this 27 years old woman who is obsessed with gaining his validation. She got no business with him. She works in the
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  • logistics, she reports to the head of logistic departments. but she often ignores the hierarchy and goes right to the director.
    via Working-Simple8753
  • My duties do not include making coffee or cleaning his desk or anything like that but I do sometimes make coffee for my colleagues if I arrive earlier. And
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  • Blonde woman talks on a phone while writing at a desk surrounded by boxes and packing paper.
    via PeopleImages

    Executive assistant on a phone call

    Photo is a representation of scenes.

  • now she makes efforts to arrive before me so she can make him coffee. I don't really like my boss's attitude towards her. he encourages this behaviour. He is busy, has meetings, barely even
    via Working-Simple8753
  • knows most of the employees here as there are so many but he etertains her. Normally we don't really have an open door policy. People cannot just enter his
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  • office. They have to talk to me first if he is free. And one day not knowing he is inside (he hed a meeting in another building) I just "stormed" inside to search some docs. and he was there and she was sitting on the desk. not
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  • in a overly provocative way, more like half sitting and one leg was swinging. and he was sitting on his chair very relaxed. and his hand was resting on the desk near her body but wasn't touching it
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  • I didn't see anything weird. like his tie was in the place if you know what I mean and her clothes too, but it still felt ... not ok. I dared to ask him about it
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  • after he asked her to leave. he said she is just very available. I was free for over a week (and I had a back up for that - who wasn't her) and she did everything for him. Papers,
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  • reports, booked his trips. I went for my back up who is a 25 years old guy and he laughed it off. he said he simply didn't have the opportunity to do anything for
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  • the boss because she was alwasy 2 steps ahead and the boss also didn't call him and he just enjoyed the free schedule and laughed. he called him just once
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  • to ask him whether he could renew his gym subscription but before he was able to do it, this woman said she will.
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  • My boss is married, has 2 teenage children and his wife is a very loving mother and wife. and she asked me out of nowehere last week if I saw anythign
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  • abnormal. I said no but I feel guilty now. she asked me to tell her if I do. What should I do. its true that my boss never really talks to random employees (not
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  • out of arrogance but simply doesnt have time for that adn is mostly just the head of departments). yet he always has time for her. forgot to say, but will add now: he went to the
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  • lunch break with her. and not to the canteen, somewhere in the city. she bragged about it, he didn't tell me anything. she sometimes brings him desserts made by her
    via Working-Simple8753
  • ok, update: I guess I made up my mind. I will not tell her anything. I don't want to be on his black list, this man is ok as a boss, but can be very cruel when he wants to be
    via Working-Simple8753

  • So the assistant walks in one day and finds her half-sitting on the desk, leg swinging, his hand resting near her body. Nothing overt enough to prove anything. Nothing that would hold up in a court of law. Just a vibe that feels like a scene from a show nobody wants to admit they watch. The boss says she is very available. The backup guy laughs because she is always two steps ahead of everyone else trying to do the same thing.

    The wife asks if anything abnormal is happening at the office. The assistant says no. The lie sits heavy. The guilt creeps in like a slow-motion close-up shot. The wife asks to be told if anything changes. The assistant now knows more than she admitted. The boss can be cruel when he wants to be. Getting on his blacklist is not worth the drama.

    This is the trap. Tell the wife and risk your job. Stay silent and carry the guilt. The boss gets to keep his little office romance going while everyone pretends nothing is happening. The wife suspects but has no proof. The young woman gets the validation she craves. The assistant gets to lie to a loving mother and wife while watching the whole thing play out like a bad episode of something that should have been cancelled after season one.

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management workplace discussion employment issues boss workplace-stories hr coworkers colleague Horrible Bosses
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