א"ר יהודה אמר רב מעשה בבתו של נקדימון בן גוריון שפסקו לה חכמים ארבע מאות זהובים לקופה של בשמים לבו ביום אמרה להם כך תפסקו לבנותיכם וענו אחריה אמן
There are 2 difference between this case and that of 65a
1. here is perfume, there was wine לציקי קדירה
2. here is daughter, there was daughter in law
1 doesn't seem to supply reason why didn't answer amen after wine לציקי קדירה because gamara there said it's OK, so no logic to disapprove and say no amen bc of disapproval.
2 doesn't seem to supply reason why didn't answer amen and in fact doing so, would be disparaging to Rabannan as if they were more careful with dealing with bloodline relative of rich person
Tos, Maharsh and others in gmara's back pages distinguish that 65a was Yabam, since husband died, they didn't answer with amen on the brocha on their own daughters but 66b husband was alive so they answered amen.
But Rashi 66b clearly states that its case also deals with a deceased husband. If so, why did they answer amen here and not on case of 65a? Can't use answer of Tosfos and also can't answer based on two remaining case differences as explained above.
א"ר יוחנן מעשה בכלתו של נקדימון בן גוריון שפסקו לה חכמים סאתים יין לציקי קדרה מערב שבת לע"ש אמרה להן כך תפסקו לבנותיכם תנא שומרת יבם היתה ולא ענו אחריה אמן
DANIEL GRAY, Toronto Canada
Shalom Daniel,
The main difference is as follows. In the case on Daf 65, the woman was not only a widow, but also a Yevamah, which means her husband died childless. This is a tragedy, and therefore the Chachamim did not answer Amen, since they didn't wish such a misfortune to befall their daughters.
However, in the case on Daf 66, the only adversity which befell the woman was that she was a widow. Generally one spouse will always pass away before the other, thus leaving the other spouse a widow or widower. Therefore, the Chachamim didn't refrain from answering Amen, because it's no use trying to avoid the normal course of events in life. The Shitah Mekubetzes and the Pnei Yehoshua both understand this way.
But the Pnei Yehoshua adds another facet; that is, assuming one spouse inevitably will outlive the other, then the Chachamim -- if anything -- would prefer their own daughter, who is their own child, to outlive her husband, who is "only" their son-in-law.
I hope this helps!
Warmest regards,
Yishai Rasowsky