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Dear Peace:
I am pleased to read this: “Me helping him financially was one time help from me”!
“Should I be more supportive?? Or should I move on.. Do you think.. my future with this ‘long distance lover’ can be full of mess”?- yes, I think that a relationship with him is likely to be full of mess because he is a mess: “he is doing nothing to change this apart from complaining”. You can be more supportive of him as long as you don’t send him money, you can be supportive by telling him something like: I hope you do what it takes to change your situation, I hope that you make the right choices for yourself!
“he is otherwise a sweetheart”- you need a man in your life who is responsible, a man who is doing what can be done to solve problems in his life, and better yet- to prevent problems from happening.
anita