A choice of Husbands in Paradise
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Question: A pious man married a pious woman and [after some time] he died. Then she married a second man who was [also] pious - and [after some time] he also died. So will the widow be a wife to the first or the second [of the two husbands] in Paradise? And did anything like this ever happen to any of the Companions [of Muhammad (sal-Allaahu 'alayhi wa sallam)]?

Response: Yes, this did occur during the time of the Companions, [whereby] one of them married a woman whose husband had died, and then [later] he [himself] died, and then a third one married her and then he died; So this occurred a lot in the time of the Companions up until our time [today].

As regards which of the [two] husbands will be hers [in Paradise], then it has been mentioned in a hadeeth on the authority of Umm Habeebah that she said: "O Messenger of Allaah! A woman from amongst us has had two husbands. When she [herself] dies and enters Paradise - with her two husbands, to which of the two will she be [a wife], the first or the last?" He (sal-Allaahu 'alayhi wa sallam) said[1]:

«She will have a choice; She will choose the one whose attitude and conduct with her was best - as he was towards her in the world [prior to death] and he will be her husband in Paradise. O Umm Habeebah! a good attitude (character) brings one the best of this world and the Hereafter» - transmitted by at-Tabaraanee in al-Mu'jam al-Kabeer.

And Allaah has the complete knowledge [of all affairs].

Muhammed ibn 'Abdillaah as-Subayyal
Fataawa wa Rasaa.il Mukhtaarah - Pages 545-546

Footnote:
[1] Shaykh al-Albaanee declared this hadeeth "munkar" in Dha'eef at-Targheeb wat-Tarheeb - Volume 2, Page 103, No.1604

Important Note: The Scholars have spoken about this topic in great detail with differing viewpoints; Time permitting, their viewpoints will be published here or on madeenah.com, inshaa.-Allaah.