• You see a disheveled person asking for tzedakka: Is he an alcoholic or drug addict, or just a person down on his luck and in need of a helping hand?

• Your friend asks you to help him find a job, but to tell the truth, you don’t think your friend is responsible or reliable. Do you offer assistance blindly or do you candidly tell him why you think he doesn’t have the right attitude for successful employment?

• A young woman whom you know is in conflict with her family asks if she can live by you: Are you offering appropriate kindness or are you enabling her to rebel against her family and sustain a feud?

Sometimes, it is hard to know whether you are doing a chessed, or you are enabling dysfunctional or maladaptive behavior. There are certain people who use others’ kindness from family or friends as a way to avoid dealing with their problems instead of genuine help to move forward. In the addiction lexicon, that is known as enabling instead of helping and it can be a draining and painful experience. Addicts, and sometimes others who are in denial about their problems, need to “hit bottom” before they can utilize help properly.

The myriad requirements of chessed in the Torah do not seem to attach qualifications to them. In fact, the Gemara Kesuvos (67b) tells a story of how Hillel the elder would fulfill the requirement of tzedakkah to provide a standard of living to the impoverished that matched their former lifestyle. For example, aside from providing the basic support, Hillel would hire a servant and horse for a wealthy person who lost his fortune. (Presumably, even Hillel’s provision of lifetysle supported charity was only when there were sufficient funds to feed those in greater need.) One time, Hillel could not find a servant for this person to escort him, and so Hillel did it himself!

How would we react today if we encountered a millionaire who lost his fortune, while still riding around in a limousine, provided by charitable funds? Apparently, the Torah attaches a great deal of weight and meaning to a person’s subjective need, and endorses the expenditure of time and money on kind and charitable acts that are unnecessary from a more objective perspective.

Does this then obligate us to assist a person in any way that the person describes his or her need, even if we believe it to be not helpful? Not necessarily so. Perhaps it is only deemed a chessed when the act feels subjectively good but objectively causes no harm. So, while it may be a kindness to offer a relatively healthy person a candy, even if it has poor or little nutritional value, just because the person asks for it. However, this would not necessarily obligate you to give a person with diabetes or other health problems a candy bar, even though he or she may subjectively be very pleased, since the actual act is not just neutral but rather harmful.

Moreover, Kli Yakkar (Shemos 23:5) makes the case that one is not obligated to help someone who makes no effort to help himself. The verse describes a situation, where you happen upon someone whose donkey is fallen under a burden you are obligated to assist him, even if it is someone whom you despise. Nevertheless, the language used is “help with him"

“If you happen upon the donkey of your enemy fallen under its load, and you hold back from helping him, you must surely work with him to assist him with unloading the donkey.”

Kliy Yakkar explains:

“The phrase ‘with him’ informs us he must specifically want to work with you. Only then are you obligated to help him. However, in a situation where he sits back and says, ‘Since you are obligated to help me, you are solely responsible’, that is why the verse states ‘and you hold back from helping him’. The implication is that when it is helping him only, and him not working along with you, then it is is indeed permitted to hold back assistance.

From here we see a rebuke to some of the impoverished people of our nation who burden the community and refuse to take upon themselves any employment despite having the ability to work or generate income for themselves and their families. Moreover, they raise a hue and cry if we do not provide them with their needed supports. This is not in accordance with Hashem’s command, as we only are to provide assistance along with their own efforts. The destitute person must make every effort to support himself, and then if he cannot fully succeed, every Jew must help him and support him with no limits."

Kli Yakkar’s position is apparently that there is no obligation of chessed or tzedakah when the recipient is lazy or otherwise not showing adequate initiative to help himself.

What about regarding spiritual matters? Are we obligated to rebuke, advise or otherwise encourage someone who clearly and willfully shirks his spiritual or religious responsibilities? Of course, we are not talking about someone who is ignorant about religious obligations, rather we are referring to someone who doesn’t express any interest or will in religious life despite knowing better.

Ohr Hachaim understands the following verse in a metaphoric manner:

“Do not ignore your friend’s donkey or ox fallen on the road, you must assist with him in picking them up.” Devarim 22:4

Ohr Hachaim explains that the fallen donkey is the person who is lost spiritually:

“This verse instructs the righteous to not ignore the sinner, even a sinner who is so far gone that he has fallen beyond hope. He must still assist him in finding his way back up. However, the verse specifically uses the language of ‘with him’ to indicate that you only are required to help him if he shows that he wants to repent. If he is fallen and does not want your help in getting back up, then he is characterized as a mocker, and Mishley (9:8) warns us not to rebuke a scoffer.”

From this Ohr Hachaim we see that even when it comes to spiritual matters, there is a limit to how much help we should offer. Specifically, so long as we sense some wish to be helped and to get out of the religious or spiritual quagmire, we can and should do everything we can to assist -- no matter how far gone and hopelessly lost is appears to be. But if the person does not even want to be helped, then we are free from any obligation.

Many of these situations require careful assessment and judgment, as it is difficult to know what is truly in another person’s heart. One fellow might appear to be lazy and unmotivated but actually doing his best to fight feelings of despair and hopelessness, while another person might give the outward appearance of cooperation and effort but actually is resisting and fighting all efforts to change. In addition, there are people who have been terribly hurt, disappointed or even abused by key religious figures or authorities such as parents or rebbes. Such individuals may show great hostility toward religious practice as a result of their trauma. On practical terms, it still might not be helpful to try to be mekarev such persons because they may be too angry, on the other hand, sometimes people secretly want to be reached out to, almost as if they are waiting for a representative of the community to apologize to them for all their hurt.  

When considering to refuse to help another person who you feel does not care enough to help himself, be it materially or spiritually, it is advisable to talk these situations over with a trusted friend who can help provide you with objective feedback. It is also helpful to discuss the halachic moral aspects with a rabbi, not just to clarify if it is technically permitted. Refusing to help a person, especially a close relative such as an addict who keeps asking for help but doesn’t take responsibility for his problems can be difficult emotionally, and twist your heart with guilt. Therefore, finding out what one’s moral obligations are does make it a little easier to say no, if that is what seems to be best.