(1) The LORD spoke to Moses, saying: (2) Tell the Israelite people to bring Me gifts; you shall accept gifts for Me from every person whose heart so moves him.
Morinis, Alan. Everyday Holiness: The Jewish Spiritual Path of Mussar (p. 151). Shambhala. Kindle Edition.
Do you rationalize rather than commit the effort it may take to be generous in a relationship?
What reasons do you give yourself to turn away?
All who give tzedekah to the poor with a frown while looking at the ground, even if they give a thousand gold coins, they lose whatever merit they might have achieved. Rather, one should give with a smile, with joy, and empathize with the recipient in their pain as it says, “Do I not weep for the unfortunate? Do I not grieve for the needy? (Eyov 31:25).”
(ז) ועוד אמר החכם: מידת הנדיבות תלויה בהרגל. כי אינו נקרא "נדיב" עד שיהא רגיל בכל עת ובכל שעה להתנדב כפי יכולתו. כי אדם שנותן למי שראוי ליתן אלף זהובים בבת אחת למי שראוי – אינו נדיב כמי שנותן אלף זהובים באלף פעמים, כל זהוב וזהוב למי שראוי לו. . . . . ועל זה אמרו רבותינו (אבות ג טו): הכל לפי רוב המעשה, ולא אמרו: "לפי גודל המעשה".
(7) Our Sages, of blessed memory, said further, "The quality of generosity depends upon habit, for a man cannot be called generous unless he gives of his own free will at all times, and at all hours, according to his ability. A man who gives a thousand gold pieces to a worthy person at one time is not as generous as one who gives a thousand gold pieces on a thousand different occasions, each to a worthy cause. For the man who gave the thousand gold pieces at one time had a sudden impulse to be generous, but after that the desire left him. . . . . Concerning this our Sages said, "Everything must be according to the multitude of the task" (Aboth 3:15); they did not say according to the greatness of the task."