re: Complicated situation. Advice appreciated. Will try to be brief.

I see your future, though it is quite blurry.

I see a broken man, literally flat broke, land seized by the Federal Government, alone in prison, sitting down while he pees for fifteen to twenty.

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wow... amazing

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you might want to heed some of the sarcastic and humorous comments here, it appears that you are playing with fire

seriously, there is something very off with someone wandering around someone's property without permission. very off. also she is connected to people in jail. you need to make it known in no uncertain terms that she is not to be on the property without your express permission. no exceptions. let her know you have a company that will be watching teh property and the sherriff is in the know. if she can't handle that or can't understand your side of it, then you need to disassociate yourself from her or you will get hurt in more ways that one--personally, financially, maybe legally

I agree with the poster that said it sounds like you have feelings for her but you know it is a bad idea. You stated a couple of times that you are concerned there is a "father figure" thing going on. Of course there is, and even though you may regret it now, you have probably promoted the father figure role. There is no other reason that you should know that much information about her personal life unless you have somewhat enjoyed participating in the father figure role and trying to give her advice. When women at work start talking personal business, get the hell out of the room!

Now, as things are coming to a head, you see that it was poor judgment to get this involved in her personal life but you can't just undue what you have already done. Perhaps the soon to be released boyfriend is what has brought the matter to its current unmanageable situation.

You need to have a conversation with her, with a witness present, and let her know she can't just hang out on your property. If she does not take the kind warning, then try the sheriff's department. However, that only works out if you have honestly not led her on in any way. Otherwise, you've got problems.

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I'm not worried about her b/f. I'm worried about liability. She's very comfortable talking to me - always has been - i just get the vibe that she views me as some kind of father figure

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You are going to get screwed, and not in a good way.

I agree with the rest of the OT who thinks your property is going to wind up being used by the BF to be a barricaded standoff set piece in some played out on TV drama where you went to talk her down and got held hostage before being shot.

You said you haven't done anything with this woman, but the way you describe her makes you sound incredibly interested. Stated her dad and youngest daughter died. How many kids does she have? Are they from the BF? Who is watching these kids while BF is in jail and she's just aimlessly wandering your property?

yea you are likely going to have a meth lab in your barn soon. prob should have this convo before her bf gets out of jail and merks you.

listening to all the good advice but some of you are way off the mark on a few things

i don't have feelings for her beyond friendship

the property is well watched by neighbors - not even a concern of mine. also a man who leases part of it is out there everyday

i'll admit she's nice to look at - won't deny that but i have zero interest in sleeping with her

there's basically 2 options here - be gentle with the situation or just run her off - that's mainly the part I was conflicted about

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ll admit she's nice to look at - won't deny that but i have zero interest in sleeping with her

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Impossible. Unless...

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you're old, you've never been married, and you have no kids

It sounds like you enjoy musical theater.

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damn