Kiddushin can be perform based on a condition. For example, we have learnt that one can perform kiddushin on condition that it will only take effect in the thirty days time. The Mishnah (3:1) however teaches that if one does so, and during that time another person performs kiddushin then she is considered married to the second man and not the first. We shall probe this ruling.
The Gemara (59b) initially records a debate about what happens after the thirty-day period. According to Rav, she remains married to the second man, while Shmuel disagrees and the kiddushin of the first man would take hold. The Gemara however rejects this understanding of the debate and explains that Rav and Shmuel were arguing about a different case. The reason is that once kiddushin of the second man takes hold during the thirty-day period, it cannot simply disappear on its own once the period expires. In other words, everyone agrees that should would remain mekudeshet (betrothed) to the second man.
What if the second man divorced her or died before the thirty-day period expires? Would the kiddushin of the first man then take hold?
The Tosfot R' Akiva Eiger cites the Ramban who maintains that she would indeed be mekudeshet to the first man. The Ramban derives this from the Mishnah that simply writes that she is mekudeshet to the second man and does not state that she is not mekudeshet to the first. In other words, the only thing preventing the kiddushin of the first man from working in the Mishnah is that once the time expires she is already mekudeshet to someone else. It is not however that the second kiddushin somehow reverted the first. Consequently, if she is no longer mekudeshet to the second man when the time expires, the first kiddushin would still work. The Ramban cites the Yerushalmi that also maintains this position.
Interestingly the Ramban continues, citing the Yerushalmi, that if the second man died during this period and she required yibum, this would also prevent the first kiddushin from working. The Ramban explains that the Yerushalmi maintains Rav's position that kiddushin in general would not work for a shomeret yabam (a women who is waiting for either yibum or chalitza). The Ramban however explains that since we rule that kiddushin does work with a shomeret yabam, she would require a get from the first man and yibum or chalitza from the brother of the second.
The Rashba however disagrees. He explains that we rule according to R' Yochanan who maintains that even if no one else came during this period, and she simply changed her mind, this would prevent the kiddushin from taking effect. The Rashba reasons that if a declaration alone can prevent the kiddushin, then certainly her accepting the kiddushin from someone else should be no different. He rejects the Ramban's proof from our Mishnah since once it states that she is mekudeshet to the second man, it is understood that she is not mekudeshet to the first.
The Ran however dismissed the Rashba's argument. The Ran accepts that in general an action demonstrating one's intent is more powerful than a declaration. He however argues that her accepting the kiddushin from the second man need not be interpreted as a complete retraction from the first. She could still be maintaining the first kiddushin if the second's does not work out during this period.1 The Ran argues that since the Gemara entertained the idea that according to Shmuel that second kiddushin would only work until the thirty days were complete, this must mean that her acceptance of the second kiddushin is not a complete rejection of the first.
In defence of the Rashba, the Tosfot R' Akiva Eiger rejects the Ran's proof. He explains that according to the original assumption, Shmuel maintains the second kiddushin would be temporary. Considering it is temporary, that is why the acceptance would not be considered a rejection of the first kiddushin. However according to the conclusion, where the acceptance of the second kiddushin would be permanent, perhaps such acceptance should indeed be considered as a rejection of the first kiddushin. Consequently no proof can be brought from the Gemara's initial assumption.
1 The Rashba brings other proofs which the Ran addresses.
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