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How/Whether to Cross the Line Between "Business" and Pleasure?


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Lately, most of the women I've met that I am interested in are colleagues (not co-workers) and women whom I volunteer with. I am really floundering with this. I don't really know when it is appropriate to cross that line between business and pleasure -- pretty stupid about the smart/ethical way to do this.


For instance, I am meeting a colleague for lunch tomorrow. She is super cute, we seen to have a lot in common, and I think that she is single or dating. I invited her, and she may just want to network, but I'd like to be friends with her and maybe more. She seems to like me, but I don't have a good sense right now of whether she is attracted to me. Hoping to get more of a sense tomorrow.


Anyway, is it sleazy or inappropriate to flirt with her or ask her out tomorrow? I plan to play it by ear, but I don't really know if it makes sense to just come right out and ask her on a date. Similarly, I've been having exchanges with colleagues/volunteer friends on Facebook, etc., and don't really know how soon (if ever) to get a little more personal. My professional reputation is important to me, and I want to go on some dates, but I don't want to start getting a reputation for hitting on too many women in my work/social circle.


Any advice on general protocol / strategy for this sort of thing would be very much appreciated!!! Especially from women. When you go to lunch with a colleague, or email on Facebook -- and there is no clear professional agenda involved in the conversation -- what is out of bounds? What are signals to send or watch out for? Thanks in advance for the help!!! I need it.

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You know the old saying, "Don't get your meat where you make your bread". Crude, but true. Unless you meet someone at work that you just have some amazingly strong chemistry with, I wouldn't advise mixing your business and personal life. Once you start doing that, you risk screwing up both of them. I personally always make a point of keeping the two in their proper spheres.

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These are not people that I work with. I have a business and these are people at other organizations in my area who do similar work or volunteer where I do -- they are not clients and I do not have any formal relationship with them.


If you don't do business with them then it's open season. I'm not sure why you think it would be intrepreted as sleazy or inappropriate. Carpe Diem!

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I asked her out. Feeling pretty proud of myself


I don't know her answer yet. It turns out that she has been dating a guy for a few months and they are starting to get serious. She said that she would think about it. I suspect that the answer will be "no", and I'm sort of bracing for that. Still, I like her a lot and I'm pretty glad that I tried, whatever happens.


Thanks for the encouragement!

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