Our Gemara on Amud Aleph tells us about the semi-annual Shidduch festival that happened on the 15th of Av and Yom Kippur. The young maidens would each promote their particular strength and virtue. The beautiful women would extoll the virtue of being attractive. say? Women with yichus would say, “Set your eyes toward family, and the children of a wife from a distinguished family will inherit her lineage.”  But the Gemara wonders, “What would the ugly ones among them say?” They would say, “Acquire your wife for the sake of Heaven, provided that you adorn us with golden jewelry after our marriage to beautify us.”

The last category, marrying a woman who is unattractive “for the sake of heaven”, does not sound like a good idea. The Gemara Kiddushin (41a) says it is forbidden to marry a woman without seeing her first, lest she be considered ugly in his eyes. We could draw a distinction, and say that in our Gemara, the person sees her first, and therefore is psychologically at peace with his choice. This is a good technical answer, but it hardly seems wise. 

I would like to offer the following explanation, based on a Mishna in Nedarim 66a, and also a careful reading of our Gemara’s text. The Mishna Nedarim tells us of a person, who apparently was feeling family pressure to marry his niece but found her too unattractive . In order to silence the pressure from his overeager relatives, he made an oath against marrying her. Rabbi Yishmael wanted to find a way to annul the oath, which can be done via a rabbinical court with the proviso that the one who made the oath expresses a changed circumstance.  He must affirm that, had he known of circumstance xyz, he would not have vowed as such. In this case, Rabbi Yishmael took matters into his own hands, and arranged for her to have a “makeover”. He then presented her to the fellow, stating, “My son, did you vow that you would not derive benefit from this woman?” (Meaning, do you now find her beautiful that you regret having made the vow, not realizing her potential?) He agreed to the Marriage and the vow was annulled. At that point, Rabbi Yishmael wept and lamented, “The daughters of Israel are beautiful, but poverty makes them ugly.” 

This was not a one-time event for Rabbi Yishmael. He apparently was accustomed to funding and providing for makeovers for young impoverished maidens of marriageable age because the Mishna reports: When Rabbi Yishmael died, the daughters of Israel raised a lamentation, saying: “Daughters of Israel, weep for Rabbi Yishmael.”

We see from here that the Talmudic Standard of attractive and unattractive was subject to remediation by investing in appropriate adornments and beautification. If so, the language of our Gemara is actually precise. The less attractive maidens do NOT merely say, “Acquire your wife for the sake of Heaven.”, which implies settling for somebody who is unattractive. Rather, they end their appeal with, “provided that you adorn us with golden jewelry after our marriage to beautify us.” Once we pay attention to it, the implication is clear. The Gemara is saying that the husbands who choose to marry these women are also responsible to invest and help them beautify themselves.