Judaism discourages loneliness and recognizes the pain of solitude. It seeks to encourage those who are alone to seek meaningful and richer lives. Hence, whenever possible, it urged remarriage. Tav le’metav tan du mi-le’matav armelo: Better to remain coupled than a widow (single).

The Rabbis showed sharp insight into the difference between first and subsequent marriages, although there is an apparent conflict. Resh Lakish says, "One should match two people only on the basis of their deeds"; Rav says, "Forty days before the creation of a child, a heavenly voice calls out: ‘So-and-so’s daughter is destined for so-and-so.’" Is there a conflict between the opinions? According to Rashi, no. "Rav is speaking of a first marriage, Resh Lakish of a second." The first marriage expresses Rav’s dictum—G‑d makes the ultimate determination. The second marriage expresses the insight of Resh Lekish—it depends on the rational, planned blending of the qualities of the soul.

There is a positive value to the suggestion that divorced couples remarry one another (machazir ge’rushato). The Torah, however, forbids a man from remarrying a former wife who had married another man in the meantime.

Unlike other religions, the Torah expected remarriage, as a matter of fact: "Lest he die in battle and another marry her" (Deuteronomy 20:7); "Then this latter man... writes her a bill of divorcement... or the man who married her last dies" (Deut. 24:3). Just as divorce frees her to marry, so does death.

There are some differences in the ceremony between first marriage and remarriage. For example, the remarried ketubah substitutes for be’tulta da (maiden) the words armalta da for the widow, and matarakhta da for the divorcee, and the amounts stipulated are changed.

The first marriage requires seven days of rejoicing; the subsequent marriages, though they may be just as joyous, require only one day of Sheva Berakhot. However, if one of the couple had never been married, the full seven days of the Sheva Berakhot are to be observed.

The veiling need not be done for a woman’s subsequent marriage. The yichud, which seals the marriage for a first-time marriage, is not necessary in a second or third marriage. Such marriages are sealed upon retirement to their home, when the couple can fully, not just symbolically, consummate the marriage. The elective elements of the ceremony—who walks down the aisle, who are the escorts, whether the children of the previous marriages should attend—are matters for intelligent and sensitive determination by the couple.

Several points should be remembered for remarriage:

  1. If the deceased husband was childless and he has a surviving brother, a chalitzah ceremony must take place.
  2. A divorcee may remarry a number of times.
  3. A divorcee may not marry a kohen.
  4. Jewish divorce must precede remarriage. This is an absolute requirement of Torah law. A civil divorce is not recognized by traditional Jewish courts. The child whose mother did not obtain a Jewish divorce from her former husband may very well be categorized as a mamzer.