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Do I lend/give money to a close family member?
My brother-in-law has been out of work for 5 months and asked me for nearly $10K today. The money will help pay medical, auto and basic needs for his family of 5. He is “80%” sure that he will be employed within 30 days with a very reputable accounting firm but, historically speaking, he hasn’t been able to secure or retain such a position since his bout with addiction 7 years ago (and has remained sober ever since.)
I am torn because I “lent” the family $20K 6 years ago and they remain underwater to this day. He is a former executive but has a history of some poor decision making despite his brilliance.
I am a single mom who, in another lifetime, earned some $ but am pretty worried about my own future now that I am earning much less and am feeling as though a “loan” will further enable the situation. However, I feel terrible with this kind of tough love approach and love my family deeply. This won’t be a loan if history repeats itself.
PS: My sister is unaware of this request…their marriage is struggling at this point due to this never ending situation.
Where is that fine line between helping and enabling??