Should I make a move or move on

So, here's the skinny. I'm head of security at this mail service, which shall remain nameless. I'm contracted to this job site, meaning I don't actually work for the mail service, but there are people on the job site that do, most of the actually.

Anyway, there's this woman who works there, which I'm almost cretin kind of has a harmless crush on my, and vise versa. I tried to figure out if she was even single before I did/said anything that would make everyday a bit awkward. She was never really straight up about it tho. Anyway, I'm pretty sure she is single.

You think it would be a wise decision to ask her out? You think even if she 'sure I'd love to', would it be a bad idea in the long run since we work on the same job site? Mind you, I only spend 20 hours a week at that particular site, and I'm in a warehouse she's in an office.

Obviously it would be pretty awkward if I asked and she said 'pfftt, no'. FYI I'm 27 she's 32. More or less should I keep it professional? Or should I do what I think we both want to do?

Thanks!

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  • In my experience, when asking someone out in a quiet moment with two people your answer will never be anything bad, and it's only down to you as to whether it gets awkward or not.

    The only circumstances I have ever encountered a "pfft, no" response was during an approach in a bar, when the subject was with a group of friends she wanted to impress. I can guarantee you'll never get that response in a 1-2-1 conversation.

    Taking that away, there's no reason not to ask! There rarely ever is!

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