A Shidduch With the Daughter of a Talmid Chochom:
His uncle sent him to learn in a yeshiva in Lithuania so that he would become fluent in Toras Nigleh before starting to learn Toras Nistar. He learned in that yeshiva for many years and excelled, becoming a tremendous talmid chochom.
One day, two men came to the yeshiva seeking a distinguished young scholar to marry their daughters. One of the men was an unlearned but very wealthy man, who also had no yichus to speak of. The second man was a talmid chochom and a man of great lineage, but he had very little money. Both of them took note of the Me'or Einayim and wanted him to become their son-in-law.
His uncle wanted him to marry the daughter of the wealthy man, but he had other ideas. He told his uncle, "It says in the Torah (Bereishis 38:2) that Yehuda took a wife who was 'the daughter of a Canaani.' Rashi explains that 'Canaani' means that he was a businessman. Why is the Torah telling us this man's occupation? I believe we can answer this question by asking another: Yehuda was a great man, yet some of his sons acted improperly, as the Torah testifies that Er and Onan were 'bad in the eyes of Hashem.' How did this happen?"
"I believe the answer is that Yehuda married for money. Instead of looking for the daughter of a talmid chochom and meyuchis, he married the daughter of a wealthy businessman, and the result was that some of his children were tainted. A proof of this is that when he later married Tamar, whom Chazal (Bereishis Rabbah 85) describe as the offspring of Noach, he bore Peretz, the father of the house of Dovid.
"Therefore, it would be better for me to marry the daughter of the talmid chochom and meyuchis." (He married his Rebbitzen Sara a"h, who was a granddaughter of Rav Yitzchok Shneira zt"l, the Rov of Kovni-Lublin, and the son of Rav Nosson Nota of Horodna zt"l, author of Sefer Mavo Ha'Shearim.)