Question:
Is a kallah who is not a besulah required to disclose this information to the chasan, and if so, at what stage of the shidduch should it be revealed?
Answer:
Yes. According to most Poskim, this information must be disclosed to the chasan prior to entering into an engagement and certainly before marriage. However, it should not be disclosed at the beginning of the shidduch process.
Rather, the information is to be revealed only after the chasan has expressed serious interest in the shidduch and there is a realistic possibility that the relationship will lead to marriage. At that point, before any final commitment is made, the matter should be disclosed.
Some Poskim rule that it is even improper, and forbidden, to divulge this information at the outset of the shidduch, prior to the first meeting, or before the shidduch has developed into a serious and viable prospect. Accordingly, disclosure should take place only once the relationship has progressed to a stage of genuine interest and potential engagement.
Sources:
Implication of Michaber E.H. 67:5; Eiyn Yitzchak E.H. 1:67 – 15; Igros Moshe O.C. 4:118 “Once it reaches a point that you wish to marry the young man, and he likewise wishes to marry you, this information must be disclosed to him. However, there is no obligation to reveal it at the very beginning of the shidduch process or before the first few meetings.”; E.H. 4:32 -4; Kovetz Teshuvos of Rav Elyashiv 1:159; Even Yisrael 9:133; Nitei Gavriel 12:28; Mishpat Hakesuba 21:27
Other opinions: Some Poskim give room for the Chasan to not be informed that his Kallah is not a Besula. [Maharsham 7:152 “A young woman who is an orphan, who had been seduced and gave birth out of wedlock, and from that time onward has conducted herself modestly and properly. Now she has become engaged from a distant location, without this matter having become known. If it would be disclosed to the chasan, he would break off the match. Now the time of the marriage has arrived, and the question is how they should proceed regarding the wording of the kesubah….. However, to actually write it differently would cause a financial loss to the groom. If this cannot be corrected through the reader’s recital, then they should arrange the kesubah with witnesses who are unaware of the matter. In addition, a document should be deposited with Beis Din, signed by witnesses, based on the orphan’s authorization, stating that she releases the husband from any kesubah obligation in excess of the amount to which she is actually entitled according to halachah.”