Feelings for married, older, female boss, what do I do?

I have recently developed feelings toward my female boss. I work at a small business and her husband is my second boss. I see both everyday of the week. I am 23, she is 37 or so. I am typically attracted to older women, and have dated one.

Oddly I have worked here for 2.5 years but over the past 2-3 weeks my feelings have gone from occasional "you look pretty" thoughts to another level, bordering utter infatuation.

Part of the issue is that she will often flirt to get people to do things, and I have accidentally stumbled upon some suspicious beyond-plationic texts with a co-worker so I feel like a have a chance; making matters much worse.

This is turning into a problem. I want to go back to not really caring for her, and not thinking about ulterior motives when she flirts to ask me to do something.

I am considering giving her a platonic oriented valentine if I can hold my feelings in. After that I'll see how things go and maybe offer a text-message confession of my feelings requesting help, perhaps a single friendly hang-out.

Any ideas? This was mostly me venting but any comments would help immensely


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Most Helpful Guy

  • It's thin Ice because it is where you make your money. I am sure she would be flattered and blush. Who knows how that would go but I would hate to lose my job over messing with the bosses wife. It may sound really far fetched but let's say she DID take you serious. Ping pong texts. She reluctantly decides to take you up on the "hang out". Next thing you know you hang out a lot and she steps outside of the marriage. You are at her place... Hubby comes home early and catches you. Least that happens is you get fired. He might just shoot you in the face.

    There are so many more women in the world with less strings and less danger. In the end you will do what you like but be prepared to deal with the result if this thing goes badly.

    Good luck

    Eagle.

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    • I do not fear losing my job, or being shot. Being discovered in bed would almost be invigorating, like a big FU to the boss-man, you know?

      I am a risk taker I guess, and don't care about consequences. They are both pushovers and I'm fairly confident that if it came down to a situation like that they would sell the business and move away, but I wouldn't lose my job.

    • Invigorating: Ahhhhh to be young and bulletproof again. This is not a game bud. This is real. They may be pushovers and like you. Both of them. The level of like and how much of a push over he is if he saw you with your hog in the woman he loves and supports could be very surprising to you. I will leave it at that. You have been warned. There will be many more "Don't do it" and for good reason. If you decide to go ahead with this. Practice your sprints til you are faster than 1100 fps

What Girls Said 3

  • STAY AWAY. Do not put yourself in that position. You may be mistaking her flirting for just being a friendly female, maybe not. But don't get tangled in that mess. You could end up harming your job or worse, be involved with some sort of sexual harassment if things go wrong. Avoid the awkwardness and treat her as your boss, not a friend.

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    • Thank you. I think a larger part of the problem is that I don't really have anyone to discuss these feelings with besides her. Its a rather racy subject that I would like to get straight from the horses mouth. Anyone who doesn't know the situation won't quite grasp my feelings, obviously saying what a terrible idea it is. Anyone who is familiar with it would be way more awkward to talk to than her. We live in a super small community and I really don't trust anyone immediate to keep matters private.

  • Why even consider this? Do you want to get fired?

    Its not worth it.

    Put your feelings aside, and remain professional (something she isn't doing).

    It is a job, not a dating lounge.

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  • Um go for someone else. Don't be a home wrecker

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What Guys Said 4

  • No. Marriage is a no-go, do not mess with that, under penalty of horrible kharma (or worse if you're a religious man). And don't fish off the company pier. Horrible horrible idea, find someone else.

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  • Dude, don't let her know how you feel, you might come across as a creep. You know you're getting into a lot of trouble with all this developing feelings thing. For many reasons just don't do it. Instead, go date other ladies that will keep your head busy.

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  • Your digging your own grave. The girl clearly married plus she just another attention seeker.why do you want to destroy somebody elses marriage. Plus keep your professional life from your personallove life sseparate

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  • This won't end well, never try to sabotage an marriage.no matter how sweet the ass looks, she said I do for a reason.

    try looking for older ass elsewhere

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