The Talmud brings a famous argument about how we dance before the bride at a wedding:
The academy of Shammai says one praises the bride as she is, the academy of Hillel says one praises the bride as being beautiful and attractive (even if she is not). Beit Shammai said to Beit Hillel: if the bride was lame or blind, can one say she is beautiful and attractive? But the Torah states: “Keep away from a false matter” (Exodus 23:7). Beit Hillel said to Beit Shammai: According to your statement, if a man acquired an inferior item from the market, should another praise it to him or disparage it to him? You must say that he should praise it to him. From here the Sages said: A person’s mind should always be sensitive to how others perceive things.
This is an amazing lesson. You may not think the bride is good looking at all, but the groom did, so much that he chose to marry her (Jewish law encourages a man to see the woman he will marry first and make sure he finds her attractive).
Since the groom found her attractive, it is appropriate and not considered lying to praise her in front of him, so he will come to love her more.
This concept is not limited to physical looks. A man may choose a certain profession, or car, or guitar that you would never consider for yourself. Your feelings on the matter don’t make his preferences invalid. Don’t judge other people’s choices by your own personal standards.
Another man may choose to build a life for himself that is totally different to what you would choose, and that is fine. Part of being mature is to understand that other people can have different values, and this does not undermine your own.
However, don’t take this idea too far. Hillel and his students chose their words carefully: you should praise an acquisition that a man made in the public market. In the public market (more like a bazaar then) there were no returns. Even if there is some flaw he cannot exchange this purchase, so you may as well praise it so he will enjoy the item he got.
However, in a situation where he can return a flawed item, it would be proper to inform the purchaser so he can resolve the situation with the seller. We don’t let our friends get ripped off.
Similarly, after a man is already married there is no benefit in telling him the flaws of his wife. However, before they are married it may be proper to inform a man that you see specific red flags in this woman. A man can become enthralled and obsessed with a woman and ignore or repress issues she has that will undermine their relationship later on.
Of course this must be done with sensitivity and only when your goal is to protect the people involved.
Red Pill Rabbi 