The blessing Jacob gives Judah concludes with the words: “his eyes will redden from wine, and his teeth white from milk.” Rabbi Yochanan says homiletically (Kesubos 111b) that you can read it as “teeth whiter than milk” — to give a smile to a friend is even greater than giving him nourishment.
When someone comes collecting charity, it is a difficult and often thankless job. Rejection can break a person’s spirits and keep him or her from continuing, no matter how important the cause. So, as it happens, a smile may be one of the most important things you can give — you can brighten that person’s spirits and enable him or her to persevere.
Closer to home, there is no one who doesn’t have a “hard day” now and then. There are great people who have tremendous internal reserves of happiness, so that no matter what, it seems like they are always happy. Even people like that need an encouraging word now and then — much less the rest of us, who sometimes just want to crawl back into bed and start over tomorrow, if not next week!
To be generous of spirit is at least as important as being generous with money — and when it comes to smiles, the more you give, the more you have!
Rabbi Yaakov Menken