Rules to Follow When Looking for a Marriage Partner
44.It is permitted to discuss another person's shortcomings only when doing so will serve some useful purpose. Otherwise, this information once again falls under the prohibition of lashon hara.
Therefore, if you see that a person does not quite understand you and will misinterpret things after hearing about certain shortcomings, you should avoid answering or say that you do not know anything. The same applies when people do not trust you and will not heed your words, or when the person making inquiries about the shidduch has similar shortcomings themselves and does not consider them significant.
45.If you know that the young people have relied entirely on their parents or other adults, and those adults have convinced them that the shidduch is advisable, it is also forbidden to disclose shortcomings. The same rule must be followed when the young people have already revealed their feelings and opened their hearts, and will certainly not listen to anything about shortcomings. (This does not refer to an illness or shortcomings involving danger or very serious inconvenience)
46.
If the person responsible for the shidduch sees that one party does not regard a particular shortcoming as serious and that the sole purpose of the questions is to obtain a "trump card," it is forbidden to disclose that shortcoming. After all, after the wedding, the spouses may use this during an argument or confrontation: "Now I understand why people said that you…", "Your former neighbor warned me. She told me what your character is like…".
Even in cases where you are permitted to tell others about shortcomings, you must make sure this will not cause the person more harm than Torah law would warrant. Therefore, if you know that the person questioning you will make the information public, or if it could harm people and sow discord, it is forbidden to tell others about it.
47.
If, as a child, a person stole, violated Shabbat or did other bad things, but has now completely reformed, it is forbidden to tell others about it now. Only if certain actions show you that they have still not rid themselves of their bad habits is it permitted to warn the other party about this.
48.If the person in question behaved very immodestly in the past and was widely known as depraved and uncontrollable, or was baptized, and so on, and you are asked about their character and youth, you must consult an experienced rabbi. On the one hand, they have already returned to the fold of Judaism, and after a few years people have forgotten their reputation as a transgressor; by revealing stories from the past, you would restore their negative image, ruin the shidduch and their entire life. On the other hand, such serious transgressions and appalling behavior indicate extreme depravity.