15He who is (A)guarantor for a stranger will surely suffer for it,
But he who hates being a guarantor is secure.
25The (A)generous man will be prosperous,
And he who (B)waters will himself be watered.
The Bible
I love the way scripture puts two diabolically opposed statements into the same passage. We are told not to be a guarantor, but it's good to be generous. We are made aware of a curse for giving, and a blessing at the same time.
I normally side with verse 25. I remember one summer at camp, there was a young man who was "trying" to get on the right track. He was apologetic for his past. He studied and spoke of the scriptures constantly. He prayed beautifully. I personally decided to invest in him and help him become a productive staff member at camp. I spoke with him, counseled, and encouraged him all I could. I even yelled at some of the people in charge because of their public distrust.
In the end, the administration was right. He got caught in sin and sent home promptly. My heart shattered. I truly believed that God would bless my investment in him. But my investment was lost.
We are constantly told to measure our investment and ensure that we are good stewards of what God has given us. We are told not to cast our pearls before swine.
While generosity is a positive thing, we must be careful who we are generous with, and to what extent we expose ourselves. If not, we can do more harm than good.