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Dating : Should I shoot my shot with a former coworker?

Dating : Should I shoot my shot with a former coworker?


I manage staff at a clinic and one of the ladies who works with me was recently fired. She is very nice, but got into an argument with a different manager and was fired for a silly reason. I always got flirtatious vibes from her, but because I was her manager I never acted on that because it would be way out of line for me to do so. Now that she’s fired, would it be worth it to send a text letting her know how I felt?

I’m still hesitant because I let her know she could use me as a reference and as a result there’s still an awkward power dynamic where she may not want to say no because she doesn’t want to risk losing a reference. I’d still give her a stellar reference either way, but she may not know that.

Should I go for it or am I out of line as her former supervisor?

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What do you think?

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  1. Wow. I was kinda involved in something similar to this recently but the reverse: I was the direct-report, and he was the supervisor. I also had a disagreement with a different supervisor and decided to quit, because I wasn’t going to be disrespected in the workplace for the wages I was receiving.

    I would say, 100% shoot your shot, but…

    You don’t know how she is feeling about her untimely departure: it could really be taking a toll on her mentally, emotionally and financially in ways that you wouldn’t know.

    Also, you offered the reference. That’s…an uncomfortable power dynamic. How does she know that you don’t just want to use her (dangling a reference over her head)? How do you know that she’s not just using you (for a good reference)?

    If you have her number, then maybe reach out to her after a couple of weeks to check in. If she is receptive of a few pleasantries, then maybe mention that you hold her in high regard and would like to get to know her personally. Do you know if she’s single and receptive to interested guys?

    I’ll let you know that it didn’t work out with my workplace crush, because, surprise, surprise, the day before I was going to ask him out, I learned that he had a son, pieced together that he probably had an SO, and realized that I couldn’t make a move.

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