We grow up learning that honesty always trumps lying. When we begin to mature, we discover nuanced situations where a little white lie is more honorable than the truth. Seinfeld describes this as a "must lie situation," a time when avoiding the truth causes no damage, whereas honesty can come off as offensive or hurtful. In the Seinfeld episode "The Hamptons," Jerry and Elaine meet their friends' baby and find that he is "one ugly baby." When the parents inquire: "isn't he gorgeous?" Jerry and Elaine find that they are confronted by a "must lie situation;" wincing in comical disgust, Jerry fibs: "so very gorgeous!"
The Torah teaches that we should "distance ourselves from lies (Exodus 23:7)," but what happens when like Jerry and Elaine we find ourselves in a situation where a white lie is seemingly necessary? Unsure whether the idea of a white lie is even tenable, the rabbis in the Talmud debate whether complete honesty is the best policy.
Shamai and Hillel––the two classical contending talmudic foes––debate this issue by posing the following question in the second chapter of Ketubot (16b-17a): What do you say to the bride at the time of dancing at a wedding? They add that we are talking about a bride who has some sort of physical defect like a limp leg or a blind eye (הרי שהיתה חיגרת או סומא).
Shamai says: כלה כמות שהיא , praise her as she actually is. This is to say that you should avoid mentioning any blemish and try to praise something about her that is worthy of praise (perhaps her shoes)
Hillel on the other hand would be in agreement with Seinfeld in that "it's a must lie situation!"
Hillel says: כלה נאה וחסודה, in all cases, tell her that she is a beautiful and graceful bride. Brides dress up and adorn themselves in jewelry with the expectation that they will receive praise from their wedding guests; it is therefore an implicit obligation of those around her to make her feel the way that she wants to feel. In the same way, Jerry and Elaine saw it fitting to answer the parents of the ugly baby with an answer that they wanted to hear.
The discussion about this scenario centers on two values which appear at odds with one another: honesty and graciousness. In the end, the rabbis (as per usual) side with Hillel and prefer that one tell a white lie to be gracious rather than tell the truth and be rude. The sages conclude that: לעולם תהא דעתו של אדם מעורבת עם הבריות, a person's mind should always be attune with people. Giving someone an unfitting compliment about a quality that they see in themselves should be considered an act of compassion. But in the end, whether or not it's appropriate to do so depends on the person and the situation.