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How Can I Trust Someone Who Says He/She Wants To Change
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Here is your answer in short form: "You cannot know, and will not know, until he or she has changed!" There is no way we mortals can read someone else's mind or heart, or predict their future. We have enough difficulty reading our own mind and heart without being deceived. But...there are some issues regarding this subject that might be enlightening.
The question as originally composed, suggested that the writer needed to know whether the person in question was sincere (read that honest) about changing given that individual's track record. That suggests to me that the inquirer's real question lies more around the issue of how much risk he or she should take with this individual. How much of his or her time, money, devotion, resources, and reputation can safely be invested in this individual with a blemished background. If this is the case, then the question is quite likely more one of safety and wisdom than anything else.
The safety issues I have seen in my office tend to fall into two camps, personal safety and psychological. Personal safety can involve both physical and material aspects. How involved (close) can the inquirer become with this individual without serious risk of physical injury. Can he or she become so involved that, if things go awry, this individual might rape (in the case of a woman inquirer), beat, disfigure, or otherwise injure the inquirer. And it can also include how much of the inquirer's resources should be put at risk of loss.
The psychological issue is a bit more vague of an area and includes such self perception issues as fear of rejection, anxiety over being unable to control or influence others, and fear of humiliation, etc. In this category I place the subject of forgiveness -- how often does the inquirer think he or she should forgive this individual?
The wisdom issue includes the inquirer's knowledge of, and willingness to live within, the principles and laws of God in human relationships. At the heart of this is the real nature of love, particularly what has come to be popularly referred to as tough love. The solution to the inquirer's question lies in living a life soundly based on God's wisdom as provided to us in His written Word. Material to all of this is the inquirer's ability to accept and live in accordance with God's principles and laws.
Trust is the first issue that comes to my mind and that is based on the principle of "reaping and sowing." This would guide me, if I was the inquirer, to let my friend know that whatever lifestyle he or she lived before is going to have consequences now and in the future, not the least of which is trust. So...he or she should not expect me or anyone else to blindly begin trusting this individual as though nothing had ever happened. The trust is going to have to be earned, this time around, and that will take time, effort, and sacrifice. If the individual is not that committed to earning trust, then no trust should be freely offered. (A check of this individual's background would likely reveal that he or she has been able to avoid many of the consequences of his or her behavior.)
Second is the issue of material aid, loans, and co-signing. There is much confusion within the church as to what and how much believers are to loan to their "brother or sister in need." A close look at scripture shows that we are to loan survival items such as food and clothing. I do not recall reading where we are to loan such things as chainsaws, automobiles, or chinaware. Apparently God left loaning those non-essential items up to us to figure out. That is far too deep of subject for this response. However, the inquirer would be "safe" to only loan survival related items to this individual. And what about money? If the money, like other material objects, is loaned for survival purposes, be prepared to lose it and consider it a gift. If the money is used for non-essentials, and not repaid, the inquirer will have to take his or her lumps for extending a hand beyond scriptural requirements. If the individual requests a co-signature, the answer is NO! And that request can come in many forms, both legal, as in a car loan, and promissory in the form of performance. That latter one can be sneaky. The individual might make a promise to perform a task for someone and ask the inquirer to carry out that promise for him or her should "something come up" that prevents his or her keeping the promise. The answer is NO.
The psychological side includes a "need" to reach out to this individual and "help" him or her. So often, that is not the case but then our hearts can be very deceptive. More often than not, it is the inquirer who is seeking help to mend old heartaches, rebuild lost esteem, or feed his or her pride. These folks can become dependent on others "needing" them in order to have some kind of foundation for self worth and significance. To that end, they become unwisely involved with hurting individuals to the point that they act like a parent to them, and/or insulate them from the natural consequences of their foolishness, and/or pay the consequences for foolishness that should impact the person whom they seek to help. On top of all that is the very real possibility that the "helping" person is trying to gain influence or control over the person being helped -- to reform him or her to the inquirer's specifications.