How do you handle knowing someone’s secret problem and the solution?

I think you are answering your own help thread. Often when we feel conflicted about something, it is because we know what we really should be doing and we are not acting in accordance to our morals and values. Either we have to change our morals and values to match our behavior or we have to acknowledge that we are not following our own ideas and change our behavior.

You do not want to be helping this lady. You feel guilty about setting boundaries with her, for whatever reason you feel like you need to help her despite the negative toll it is having on you. You highlight her codependency, but that is behavior you are mirroring back to her.

I think the reason you are drawn to helping this lady and so distressed by her at the same time is that you see your own behavior in her actions and you are using her as a distraction from yourself. The reality is that you have no obligation to help her and you're stressing yourself out over this for no reason. If she wants your help, she will respect your boundaries. If she won't respect your boundaries eventually you will have less and less contact with her and she will lose what little of a relationship she has, like has happened in the past. You may feel like you are having empathy for her by dealing with her despite her issues, and we ALL have issues, but clearly she is not learning certain social rules and you are in some sense enabling her by continuing your relationship at the behest of yourself. If she is a danger to herself you can send a report to social services but honestly, at this point, listen to yourself and respect yourself. Stop guilting yourself for communicating your needs in a relationship and feeling hurt when you aren't getting them met. You are not being paid to take care of her, if this was a professional situation yes it doesn't matter if the relationship is mutually beneficial because you have a financial incentive. That's not the case here.

Really. Listen to yourself. You're the one saying all of this, not me. It's scattered in your post.

Nail on the head. It's true. That's why I know what's up. I guess I feel because she is intelligent and she showed me her self-help books on Safe People and Boundaries, she'd take the news of her codependency ok and be fine. But this tendency and life skills are something she has to be ready to see and ready to build on over time on her own. It's just too bad so much of her life is over. Also, as a Christian I am called to care for everyone, especially a fellow believer. It's just she doesn't want real help. She wants a controlled "relationship." That's why everyone has run from her. :(
 
Your solution is to tell her something?

I feel like I've missed something [significant] here. Telling people what's wrong with their life approach hasn't yielded good results for me. Perhaps I'm doing it wrong?

That being said. If you feel it could lead to professional counseling, it may not be a bad idea. Judging by your personal perspective of their situation, that's what they need.

What do you think? @MsLonelyHearts

Yes, thanks. See my reply to @slant. I actually don't think she is ready to hear what is holding her back. It's really sad because I can feel the pain she must have sometimes.
 
Yes, thanks. See my reply to @slant. I actually don't think she is ready to hear what is holding her back. It's really sad because I can feel the pain she must have sometimes.
Yeah 60 years of learned behavior, however dysfunctional, has worked for her. Doubt she'd change it now. More likely she'll be offended and start gossiping about you to the next shark she decides to pilotfish.

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