Why There Is Concern About Marrying a Widow

To the questioner, Here is a comprehensive answer on the matter, from the author of Peninei Halacha: "Some of the sages said that although according to the law it is permitted to marry a widow three months after her husband’s death, nevertheless they recommended not marrying her, for their reason was that, according to Kabbalah, there can be an objection on the part of the soul of the deceased against the one who marries his widow, and this objection may cause danger to the groom or to the widow (Responsa Chaim Shaal 2:19, Maharam Shik, part 2, Kama), and there are great authorities who did not concern themselves with this at all. There are those who hold that if there is room for concern, it is only within twelve months of his passing, but afterward there is certainly no need for concern. (See Nisuin Kehilchatah 2:53.) It is told of the Vilna Gaon that he himself married a widow who was the daughter of a Torah scholar. And some are concerned about this and perform a special tikkun for them. In any case, if a person is concerned about danger, he should say the tikkun of the Rashash, and with that he will be saved from danger (Rav Paalim 2, Sod Yesharim 1). "By contrast, it is brought in the book Bnei Yissachar in the name of the Maggid of Mezritch, the great disciple of the Baal Shem Tov and the teacher of the great leaders of Chassidut, that not only is there no need to be concerned that the widow will marry, but if the widow is fit to marry, then for as long as she does not marry, there is no ascent for the soul of her deceased husband. This is because, as it were, because of him his widow remains lonely and wretched, and this is counted against him. "And if the widow has children, then by marrying her one fulfills a double and redoubled mitzvah: in addition to the mitzvah of marriage, there is also an element of kindness and charity of the highest degree. For the Talmud in tractate Ketubot (50a) cites the verse, 'Ashrei shomrei mishpat oseh tzedakah bechol eit' (Tehillim 106:3), and the Sages ask: Is it possible for a person to perform charity at all times? If so, who is this blessed one who does charity always? Rabbi Shmuel bar Nachmani answers: This refers to one who raises an orphan boy and an orphan girl in his home and arranges their marriages."