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Re: in debt for ever?
You basically need to open up to him with your feelings about the entire situation. Keeping calm and non confrontational, you need to let him know how much you appreciate his kindness in helping you...but you also want him to know you are working on your finances and have made a lot of improvements. Make him understand that in order to complete your financial transformation, you must fly solo without his interference. Say it kindly but firmly.
Finances are a very significant reason for turmoil in relationships. Get all the help you can to get a handle on your budgeting and spending. There are many psychological reasons why people get themselves into heavy debt. If you have not gotten help to get to the core issues of your tendency to overspend, then it's likely you will continue this vicious debt cycle forever. Most often, people who have spending and budgeting problems have emotional issues which reach way back to their childhood. There are many who were simply never taught self-discipline or basic home economics.
Right now, have this talk with him...talk until it is completely resolved. But you are going to have to clearly understand that no relationship you are ever in will be on solid ground unless you are able to get your financial house in order.
It sounds like you've got a really good guy here, although I don't really think he does you any favors by bailing you out every time you come up short. If he continues to do that, you have no serious motivation to keep your spending in check. Keep this guy around, though!!!
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