As a professional matchmaker, and someone who has helped more than 400 people get married over the past 17 years -- I can tell you that the topic of 'settling' is one that rankles virtually all singles.
This is one of the most delicate topics imaginable, and it arises when it becomes necessary to tell a person that they should ‘cut their losses,’ accept what’s out there in the singles market, and perhaps even ‘settle’ for someone a little bit less spectacular than what he or she originally hoped for.
Rav Yosef Eliyahu Henkin, ZTL saw this message contained in a famous passage in the Talmud (Gittin 56a).
The Talmud there relates that Marsa bas Baisus was the richest woman in Jerusalem at the end of the Second Temple period. Her wealth notwithstanding, she too suffered from hunger during the Roman siege on Jerusalem.
As such, she sent out her agent and instructed him to bring her bread made of fine flour.
Unfortunately, by the time he went, it had all been sold. He returned and told her there’s no bread of fine flour, but that there is still white bread (ie. a lesser product), to which she agreed.
However, by the time he arrived, all of the white bread had been sold. Again he returned, and he related that while there is no white bread, there remains coarse bread in the market place.
Reluctantly, she accepted this and instructed the servant to bring her some.
Once again, by the time he arrived, it had been sold. The servant then told Marsa that the only remaining item in the market place was barley flour.
Lo and behold, by the time she agreed to accept it, there was no more remaining of it in the marketplace, and shortly thereafter, Marsa died.
Rav Henkin saw in this Talmudic passage a warning to all single people seeking their spouse.
Beware! You must know that there may be a time to cut your losses and accept a ‘lesser’ match than you had originally hoped for.
Beware of delaying, because in many instances, by the time you reluctantly accept to date a certain ‘type’ of person you hadn't been considering before (ex. less wealthy, divorced, someone with children from a previous marriage, some a little bit older than you preferred, etc), the high-quality members of that group might no longer even be available on the singles scene, and you run the real risk of ending up with no one!
A wise person will allow other competent, caring individuals to get involved and help him find a suitable match, or at least be open to their input -- whether as to timing or otherwise. This was the practice of the Patriarch Yitzchak, who openly agreed to his father’s matchmaking suggestions, as well as Eliezer’s role as his matchmaking agent.
Experience shows that one cannot rely solely upon one's own assessments in picking a good spouse for oneself, because a person is undoubtedly not objective.
In fact, this explains the ‘phenomenon’ of a young person getting married and shortly thereafter ‘discovering’ that the spouse of their choice no longer possesses the characteristics and qualities they believed the other person possessed!
Unfortunately, we find in today’s world that most people are making their marriage decisions -- the when and the who -- with more autonomy than ever before, but instead of this bringing divorce rate down, the number of broken homes and marriages has skyrocketed!
The overwhelming number of singles I encounter would be well-served to emulate the timeless example of Yitzchak.
He gladly acquiesced to receiving loving, wise help and a third-party perspective in finding a suitable spouse, and ultimately was blessed by meeting Rivkah, the second Matriarch of the nascent Jewish nation.