The Torah tells us at the end of Parshas Pinchos, that Bnei Yisroel brought thirteen cows as sacrifices on the first day of Sukkos, and day by day as the Yom Tov progressed, the number of cows steadily decreased. On the second day, only twelve cows were offered on the mizbeiach and so on, until the last day when only seven cows were brought as karbonos. Rashi quotes a Medrash to explain this practice. The Medrash writes that the Torah is teaching us the proper procedure (derech eretz) for hosting a guest. Just as the sacrifices decreased in number day after day, so too says the Torah, there should be a steady decrease in the type of food offered to one’s guest. The first day he should feed his guest fattened fowl, the following day he should feed him fish, thereafter meat, then legumes and after that vegetables.
Rav Wolbe asks (Shiurei Chumash Parshas Pinchos) that this does not seem to be the proper way to act at all. At this rate, in another few days he won’t feed his guest anything! He answers with an explanation offered by his father-in-law, Rav Avrohom Grodzhinski zt"l:When Chazal tell us that the Torah is teaching us the proper procedure of hosting a guest, this means the way one should conduct himself so that his guest feels completely at home. The first few days the guest is served lavish meals in the dining room on the table reserved for Shabbos. Afterwards he is cajoled into joining the family in the kitchen and eating the same food as the rest of the members in the house. This is the derecheretz to which the Medrash was referring; slowly but surely decreasing the difference between the guest and the host, until the guest feels at home and even part of the family.
Rav Wolbe writes (Alei Shur vol. II pg. 204), that often other areas of chesed also require some level of tact to ensure that the beneficiary is left with a good feeling. He relates how there was a man in dire straits but nevertheless was embarrassed to accept a monetary donation or loan. A good friend devised a plan to help him out. While in the company of his needy friend, he acted nervous and uneasy. The needy friend inquired as to the reason behind his distress, and he explained that an elderly man whom he used to visit often, had passed away and entrusted him with a large amount of money to distribute to those in need. He added that he is nervous to carry so much money around with him, and he doesn’t know where to start with its distribution. The needy individual smiled broadly and told him that he would put his worries to rest, for just now he was tight on money and he could use the amount of money his good friend was carrying. The latter handed over the money and the needy man felt that he was doing his friend a real favor!
Whether one is hosting a total stranger or helping out a good friend, the aim of the chesed is the same: Helping out a fellow Jew in a way that will make him feel comfortable and completely at ease.