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Older female boss basically admitted she wants to sleep with me

kevinhart

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Feb 10, 2018
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I'm posting this here, because it's as good a place as any for anonymous advice.

Basically, I'm a man in my late 30s who used to work with a woman in her late 40s in the same office. She got promoted to manager of the office. There was always a bit of flirting as colleagues, with her assigning me as her work husband and bringing me baked goods and such, but I never thought anything of it. When she was promoted, I assumed that she, being a seasoned professional who had been through thick and thin in her career, would act professionally and everything would be fine.

But an interesting turn of events has occurred. I became somewhat envious that she was promoted and not me, so I began to test my new boss' boundaries a bit in terms of what I could get away with, in terms of work rules. I knew I was being obnoxious, but everything I was doing was within the realm of the rules, just sort of pushing them to annoy her a little bit. Then she started to push my boundaries too as my boss, so we both sort of decided to stop and get along. Again, no rules were broken during this era, we were both just trying to annoy each other.

When I asked her, in veiled terms, why we couldn't get along anymore, she basically admitted it's because she was sexually attracted to me. The exact statement went something like this: I was analogizing she and I to two former colleagues, a male and a female, who fought with each other just as my boss and I were fighting. I asked her why those two other colleagues just couldn't seem to get along with each other, which was my indirect and passive-aggressive way of asking my boss why she and I couldn't get along with each other. She replied that it was because they wanted to sleep with each other. She might have even used the phrase, "They wanted to f*ck each other," and that's why they couldn't get along. So I took that to mean that my female boss was telling me that she and I couldn't get along because we wanted to sleep together, or at least she wanted to sleep with me. This sort of seems like something out of one of those HR videos that everyone makes fun of all the time.

This happened on a Friday. On Monday, my boss was clearly freaking out about what she had said. She made sure that a colleague was in the room with us each time we spoke that day, and two of her female associates (who I suspect had been the ones who told her that this was a big mistake) were calling her frantically all day and she kept making excuses about the calls that were clearly bad lies (my boss can't lie very well).

Ever since then, I've been documenting everything, but here's the thing: it doesn't really bother me that my boss wants to sleep with me, I just don't want it to affect my work nor do I want my boss and I not to trust each other. If she and I can never be in a room alone together again without one of us worried about the other, how is that going to work for us?

The other thing that is sort of sad is that my boss doesn't deserve to be fired or let go or have her reputation hurt. She is a good person who probably has Asperger's and has spent her whole career defending those in need in a genuine way. She likes working with troubled children, animals, and she especially likes misunderstood types, like sociopathic young people, pitbulls, etc. I don't feel that someone with a good heart who is on the autism spectrum should be dinged for not knowing where the boundary was. At the same time, I don't know what to do to both protect myself and protect her. I.e., what if I act like nothing's happened, but her dingbat female friends get her all worked up and try to convince her to get some dirt on me or something? I don't want to feel that I have to watch my back.

I also have a bit of a strategic side to me as well, and for the last year I've been trying to transfer to an office in the same company closer to home, so I won't have to drive so far every day. Upper management keeps saying no because my current office is out in the boonies and they had no one to replace me in that office. But now they are short several people in lots of more plum offices closer to where I live. One of those offices is a place where I would have a fellow male manager, who likes me a lot and whose staff thinks of me as one of their own. It seems like this might actually be a good time to put in for transfer, and my current boss would find that beneficial too given what's taken place. But at the same time, I feel like me transferring because of what transpired is almost the equivalent of being pushed out for not doing anything wrong. Even if it works for everyone --- my current boss, myself, and the company --- it seems unfair in a way. If the shoe was on the other foot and a female employee transferred because of a male boss admitting sexual interest, everyone from lawyers to the media would act like that male boss was the worst person who ever lived. So I'm not sure what I should do here. I would appreciate any input.

(And yes, I will be honest, I am a red blooded male and I have found myself fantasizing about naughty office sex with this woman, but at the same time, I know that this wouldn't end well for anyone.)
 
Well, I've never been in this position, but it seems like you genuinely care about this woman and don't want to see her hurt or punished for what is basically a slip of the tongue. If you had the opportunity to speak to her one-on-one and clear the air would you take it? Given that she's navigated the business there seemingly well, it might be best just to establish some ground rules, if you will, about you being friends and the limits of that. If you still wanted to transfer you could make the case to her that it isn't about her, but the convenience of the alternate location and maybe she could help you achieve that transfer. Mostly, my best advice is to approach the situation in a way that won't put her on the defensive. It sounds like you recognize that she's a human with feelings that in any other situation would be a good thing and so I think you're in a good position to give her a graceful way out.
Again, having never been in this situation this is just what I think is the best way for a resolution that is good for both of you and preserves privacy and each other's feelings, whatever they are.
Keep us updated though, I'm curious as to how this turns out.
HappyD
 
You were trying to transfer before this all happened and you couldn't. You now have a chance to transfer. What happened between you and your boss in no way invalidates the logical reasons you already have for transferring. Don't let pride or ego get in the way of a logical choice with more benefits then not.

Secondly, you say you like this person, and by moving it would resolve many of the issues that have arisen lately. It just makes sense to leave.
 
I'd say just briefly talk to her and say tell her that you don't plan on reporting to the upper levels of the company and that she's not in trouble and that's she's a nice and lovely woman but your not ready to start a relationship at this time in your life so while your flattered you'll have to decline. Basically be a gentleman about the whole thing, there's no need to get mean about this. ^_^
 
You were trying to transfer before this all happened and you couldn't. You now have a chance to transfer. What happened between you and your boss in no way invalidates the logical reasons you already have for transferring. Don't let pride or ego get in the way of a logical choice with more benefits then not.

Secondly, you say you like this person, and by moving it would resolve many of the issues that have arisen lately. It just makes sense to leave.

And don't admit anything or even make references to being attracted, nothing awkward or even vaguely inappropriate that could be used against you if taped.

If her friends made her paranoid, and if other people get access to any tape or documentation of you saying anything that could be considered anything but professional, someone else could use it against you.

I'd speak generically about "getting along" at most, if you address it at all. I'd just stay positive, friendly & ignore the slip entirely.

Always speak as if the CEO and Board of Directors are in the same room.
 
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