"You may not take a widow’s garment as security” (24:17)
The Torah warns, “You may not take a widow’s garment as security”, even in reference to a widow who is wealthy (Sefer Hamitzvos prohibition 241). Now, it could be the case that the lender does not intend to pain the widow at all by taking her garment as security, and since she is wealthy it is extremely unlikely that she will become upset. Furthermore, by failing to take any security, the lender is actually endangering his own assets. Nevertheless, he “may not take a widow’s garment as security,” for there is a remote possibility that, for a widow, this may be a distressing experience.
From this we can learn that even in a situation where: a.) It appears unlikely that somebody will be hurt by one’s actions; b.) There is no intention to hurt another’s feelings; and c.) One suffers a personal loss—nevertheless, there remains an obligation to “love your fellow like (you love) yourself.”
(Based on Sicha of 5th night of Chanukah 5747)