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I'm interested in what the teaching of the Jewish religion is on a man marrying a woman who had a deceased husband? Is there further considerations in regards to whether the widow has children. A woman cannot with the best intentions be a father to her boys would it be OK to have a second man in her life to help with male role models for her boys?

Would it be better for them to marry or could a living arrangement that is beneficial to both widows be made for the children that does not involve marriage?

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  • Sefer hachinuch on a Kohen gadol marrying a widow come to mind. And Pesachim 112a
    – robev
    Jul 29 at 18:45
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    Except for certain rare cases that are extremely unlikely to apply, a man is completely permitted to marry a widow. If the woman was instead divorced, it would be permitted as long as the man is not a kohen (member of the priestly class)
    – Daniel
    Jul 29 at 19:32
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    As life expectancy used to be far shorter, blended families were incredibly common. Talmud's tractate of Kesubos goes through all sorts of cases of a spouse bringing in children from a previous marriage.
    – Shalom
    Jul 29 at 19:56
  • Are the rules the same for women? I know I did specify men in the question. I will post it as a separate question if need be.
    – Neil Meyer
    Jul 30 at 7:34
  • @Shalom could you post some of those cases as an answer. I would love to read a full account.
    – Neil Meyer
    Jul 30 at 7:36
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In Judaism, the only person who is restricted from marrying a widow is the high priest, a position which unfortunately does not exist nowadays. In fact, many of Judaism's greatest leaders married widows (e.g. King David, Rava).

With regard to blended families, there may be some potential issues regarding yichud (isolation with a member of the opposite sex) but there are generally accepted workarounds in cases of need such as these. As always, AYLOR.

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