Question: I have been told that you may not compliment a person if you do not mean it——so how do you go about when a friend wears something and in my opinion I think it looks bad and she asks how do I look? What should I say?
Answer: Thank you for asking this important question. I think that the best way to answer this question is to first establish what speech is.
In Judaism, we consider speech to be equivalent to the divine power of creation. Therefore when speaking to a person we must understand that a person was created in the image of god. With that in mind you are correct in saying that one should always try their best to speak the truth.
However, sometimes the truth can be more harmful if stated the wrong way. If a person is wearing something that they enjoy wearing but someone else believes that it looks bad telling them will only hurt them. There is no constructive purpose and telling someone that what they’re wearing looks bad. Therefore, because we as Jews value speech and we do not believe in the old saying, “sticks and stones may break my bones but words will never hurt me” we therefore are obligated to be mindful of a person’s feelings at all times. Bones do heal, but words stay in a person’s mind forever.
Instead of commenting on your friends clothing ask her if she would like to go shopping and suggest things that you believe would look good on her. This way, you are not hurting her feelings but you are helping her to see the truth about the way she looks in a helpful way.