Torah Portion: Mishpatim
…if she is not pleasing to [her master], he must let her be redeemed (Shemos 21:8).
It is a positive commandment to designate a Hebrew maidservant [for betrothal]. That is, the Israelite man who purchased a Hebrew maidservant is commanded to either marry her himself or to give her to his son for a wife—as it is written, If she is not pleasing to [her master], who has designated her for himself, then he must let her be redeemed (Shemos 21:2). Our Sages of blessed memory said that Scripture is alluding here that there is a mitzvah of designating for betrothal.
Among the roots of this mitzvah is the idea that God had compassion on the poor girl who was sold, and on her father who was compelled to sell her. He therefore commanded the one who purchased her to take her for a wife and to make her a mistress [over his home], for He is a gracious and compassionate God. And if the purchaser does not desire her for himself, he is to marry her to his son; for with her master’s son she will equally be happy and rejoice. Or else he is to deduct from her redemption price and thereby help her go free of servitude rather than cause her to remain under his ownership until the end of the full period of the purchase—even if he is pleased with her work. All this stems from the loving-kindness of God for His creatures.
This mitzvah applies only at the time that the Yovel year is in effect. One who transgresses it and designates her for betrothal neither to himself nor to his son, nor does he help her achieve her redemption, then he has not observed this mitzvah. However, it seems that he is not forced to fulfill this mitzvah. Nevertheless, if he did marry her or gave her in marriage to his son, as we have said, he has acted worthily; blessing shall come upon him; and it is befitting that good and worthy sons will come from them.