What To Do When Students Ask For Help?

This should be a Will Okun post, but I'll give it a try:

There's a scene in the HBO drama "The Wire" where a former student comes back to his old elementary student to see a favorite teacher and ask for help. The student had been one of the teacher's favorites, and had done better academically than his friends despite severe disadvantages. However, he's dropped out of high school and shown up after school, asking the teacher for money to get a place and get off the street. After hesitating, the teacher says he'll help. Turns out the money was for drugs.

What do you do when students -- current or former -- ask you for help, financially or otherwise? Do you help? Do you not?

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