Rambam, Mishneh Torah: Gifts to the Poor 10:4
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רמב"ם הלכות מתנות עניים פרק י: הלכה ד
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כל הנותן צדקה לעני בסבר פנים רעות ופניו כבושות בקרקע אפילו נתן לו אלף זהובים אבד זכותו והפסידה, אלא נותן לו בסבר פנים יפות ובשמחה ומתאונן עמו על צרתו שנאמר אם לא בכיתי לקשה יום עגמה נפשי לאביון, ומדבר לו דברי תחנונים ונחומים שנאמר ולב אלמנה ארנין.
Whenever a person gives charity to a poor person with an unpleasant countenance and with his face buried in the earth, he loses and destroys his merit even if he gives him 1000 gold pieces. Instead, she should give her with a pleasant countenance and with happiness, commiserating with her about her troubles, as [Job 30:25] states: "Did I not weep for those who face difficult times; did not my soul feel sorrow for the destitute?" And he should speak to him words of sympathy and comfort, as [ibid. 29:13] states: "I would bring joy to a widow's heart." [Translation by Eliyahu Touger. Edited for gender neutrality]
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Suggested Discussion Questions:

1. What type of behavior must we avoid when giving tzedakah? Why?

2. How should we act when giving tzedakah? Why?

3. Why does tzedakah often make us uncomfortable? How can we combat these tendencies?

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Time Period: Medieval (Geonim through the 16th Century)