I have worked with my secretary for a couple of months. She’s extremely intelligent and diligent and I appreciate her work every day. I have had a bit of a crush of her for a bit but never mentioned it due to the supervisor-report dynamic. I believe she may have reciprocal feelings though.

She texts me outside of work about personal things or just to talk, and is flirtatious over text and in person, though never to a degree that would be totally unprofessional. We communicate well beyond what would be the norm (texting together at 2:00am on a Saturday, etc)

I think we’d genuinely be a good match, my workplace has no specific policies against workplace romance but I want to make sure that I don’t bring this up in a way that would create an uncomfortable environment for her if I’ve misread the situation (though I am very certain this is a mutual feeling).

What would be the most appropriate way to pursue a relationship?

Tl;dr I think me secretary and I have a mutual crush, how do we appropriately pursue a relationship?

3 comments
  1. You can’t date her as your subordinate. You just can’t. It puts you both in disadvantageous positions. Can she be someone else’s secretary or take a position that wouldn’t directly report to you?

    Personally, one of us would have to change employers. I’m not running personal matters through HR.

  2. Do NOT make the first move. It’s extremely dangerous for a male superior. If you really do like each other, it would be best if either of you changes company. Every other employee would be “she fucked her way for a christmas bonus” or whatever. Everything good she will ever do or gets will be tainted. “Oh, i bet she slept with the boss for that raise”. Also keep in mind that she may actually be malicious as well and really fuck her way to the top. All kinds of people exist.

  3. let me give you some serious advice.

    i am a lot older than you and got into a relationship with a beautiful, sexy, seductive younger woman at work. she is management, i am not. we were together for 18 months. we got engaged, then there was suspected infidelity, gaslighting, manipulation, belittling etc. she absolutely broke me psychologically and emotionally. i had 3 months off of work where she broke up with me.

    i went back to work this week and she is flirting with other staff, dressing like she’s going clubbing or on a date, not very appropriate for management. she is stepping up to a higher position next month, so my life will be hell as she will have authority over me. she is a narc, she is messed up, she is not stable. no one will believe what she is if i tell them and what she did to me. i am currently looking for another job. i was on my way to healing before i went back to work and seeing her and interracting with her has put me many steps back. she does not care for me, she has no interest other than climbing up the corporate ladder. i asked if we could meet up outside of work just to draw a line under things and she will not even give me that.

    DO NOT FLIRT/TEXT/GET INVOLVED WITH YOUR SECRETARY. SHE WILL F*CK YOU UP FOR LIFE! YOUR CAREER WILL BE OVER. IF YOU DO NOT LISTEN TO MY ADVICE THEN THAT IS YOUR DOWNFALL.

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