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Assuming Ann is Catholic and married to Bob. She later gets a civil divorce from Bob and gets married outside the church to Chris. Bob later dies.

Is Ann's new marriage now valid? If not, can she get a dispensation? Or does she need to marry Chris a second time?

3

Canon lawyer Cathy Caridi has actually discussed this very question on her blog, Canon Law Made Easy.

To briefly summarize her excellent article, canon law, following Catholic theology, does not recognize divorce as the end of a marriage, and so not recognize the validity of a marriage while either potential spouse is currently married. It follows that Ann and Chris are not, in the eyes of the Church, married at all. And of course it follows from that that there's no second marriage to become valid.

What Ann and Chris need to do to "regularize their situation" (that is, to ensure that they are living within the rules of the Church, but more importantly that they are living their lives rightly before God) is, firstly, to talk to their parish priest. It is likely that he will want to discuss the whole situation with them, and understand how they came to this point and what they understand of the Church's understanding of marriage. They will need to go to Confession and confess their sins, including the sin of adultery (which they committed by living together while Ann and Bob were still married, that is, while Bob was living) as well as fornication (which they committed by living together without marriage after Bob's death).

Then what? They certainly have an existing relationship, which they presumably believed was a real marriage. What they have to do now is to get that "putative marriage" (as it's technically called) validated. This can happen through the processes of radical sanation or convalidation (the likely next step in this case). How this is done is well explained in Andrew Leach's answer here as well as in other answers about validation of a marriage throughout this site.

  • Also if I were the priest I wouldn't allow Ann marry Chris but as a penance, after the confession, I would command her to stay single and abstain from any future relationships in order to offer reparation for the harm she caused to Bob and God. But I know today's priest are weak and cause people to suffer in purgatory instead of here on earth. – Grasper Aug 1 '17 at 12:29
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    I agree with most of this answer, but it seems to me that "sin of fornication" applies to the time after Bob died; while Bob was alive, sexual intercourse between Alice and Chris was adultery, not formication. – Andreas Blass Aug 1 '17 at 23:52
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Ann would be in an invalid marriage with Chris:

Can. 1085 §1. A person bound by the bond of a prior marriage, even if it was not consummated, invalidly attempts marriage.

§2. Even if the prior marriage is invalid or dissolved for any reason,* it is not on that account permitted to contract another before the nullity or dissolution of the prior marriage is established legitimately and certainly.

*such as by Bob's death, as in your scenario

Ann would have to convalidate her marriage (i.e., marry Chris).

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