
(1) ויהי בעת ההיא וירד יהודה, after Joseph had been sold. The fact that the Torah speaks of וירד, “he descended,” seems to imply that Dotan was situated at a much higher elevation than Adulam. According to a Midrash quoted by Rashi, the word וירד does not refer to a physical descent but to the brothers having demoted Yehudah from his role of their leader as they held him responsible for the debacle with Joseph. They had repented their part in the whole episode, and they accused Yehudah of not having been firm enough. Just as they had listened to him when he told them not to kill Joseph, they claimed that they would have listened to him if he had suggested that they should bring him back to their father. In Bereshit Rabbah 85,2 the whole paragraph commencing with וירד יהודה until the beginning of chapter 39 is considered as not relevant to the story, at least not at this point. Why then did the Torah insert this episode here thereby spoiling our concentration on what would happen to Joseph? According to Rabbi Eliezer the Torah wanted to create a conceptual link between one “descent,” and another “descent.” Rabbi Yochanan justifies the “interruption,” by linking one הכר נא “please identify!” to another הכר נא. Yehudah had deceived his father with these words, whereas Tamar reminded Yehudah that he had been deceived by her and that his assumption that she was a harlot who had become pregnant by her customer was totally unfounded.(compare 37,2 and 38,25 respectively)
AT THIS TIME. This is not the time that Yosef was sold, rather this was prior to his sale. We see the same occurrence relating to when the tribe of Levi were separated. Why then is the story of Yehuda placed in the middle of the story of the sale of Yosef (if Yehuda's story was much earlier)? To separate the story of his sale to the story of Potiphar's wife. I am obliged to explain this becuase from the day that Yosef was sold until the day that the entire family descended to Egypt was 22 years. Onan was born and he was Yehuda's second child, he had his own children which makes him at least 12 years old. Furthermore, Tamar was pregnant and gave birth to Peretz who descended to Egypt and had two sons. Don't question about Betzalel's heritage as I address that elsewhere.
THE DAUGHTER OF A CANAANITE Onkelos says 'a merchant' who came to dwell in the land. His thought process is since the sons of Yaakov were not permitted to marry Canaanites like their fathers Yitzchak and Avraham. It states in Pesachim: they married Egyptians, Ammonites, Moabites, Ishmaelites and from Ketura's family. This is why Shimon is singled out for marrying the father of Shaul. Only he married a Canaanite. There is a midrash that Shimon married Dina. R.Yehuda says that all of the children of Jacob married (their half-brothers') twin sisters. R. Nehemia says they married Canaanites. According to R.Nehemia the ones they married were strangers and immigrants from the other nations because it doesn't make sense to him that they married their sisters which was forbidden according to the Noachide laws.
ועל דרך סברא איננו נכון שישאו כלם כנעניות שיהיה בנוחלי הארץ מזרע כנען העבד הארור... והראוי היה שפירש בו שהוא תגר שאיננו מן הארץ שהיתה לחוי או לאמורי ... וכן תמר היתה בת אחת מן הגרים בארץ לא בת איש כנעני ביחוסו כי חלילה שיהיה אדוננו דוד ומשיח צדקנו שיגלה לנו במהרה מזרע כנען העבד המקולל ורבותינו אמרו (ב"ר פה י) בתמר שהיתה בתו של שם והוא כהן לאל עליון
According to logic, they did not marry Canaanites who descended from Canaan who was cursed along with his descendants. What makes sense is that Yehuda took a wife who was not from Canaan, rather a Hittite or Amorite who was dwelling in Canaan... God forbid that David and the Mashiach come from the cursed eternal slave Canaan. Our rabbis stated in the Midrash that Tamar was the daughter of Shem, the High Priest (brother of Cham, Canaan's father)
(א) בת איש כנעני, ולא זכר שמה אלא אביה ולא ידענו למה, וכנעני כתרגומו סוחר היה משאר האומות והתגורר שם, כי בני יעקב היו נזהרים מלהתחתן עם בנות כנען כמו האבות, כי שמעון שלקח אשה מבנות כנען זכרו לגנאי והפרידו מאחיו ואמר ושאול בן הכנענית.
(א) הבה נא אבא אליך. היה ראוי הכתוב לומר הבי, אבל מפני שהיתה בעינו זונה תובעת בפה כמנהג הזכר לכך שנה הכתוב ודבר לה בלשון זכר.
(1) . הבה נא אבא אליך, “if you please, I wish to have relations with you.” If the Torah had applied the rules of grammar here, it should have quoted Yehudah as saying הבי instead of הבה. However, seeing that Yehudah considered the woman a harlot, a woman who demands sexual relations outright in the manner males do, he changed his mode of address and treated her as if she were a male. The Torah preferred to quote Yehudah verbatim instead of observing the rules of grammar.
(2) ותשרף, according to the plain meaning of the text this was the standard penalty for a widow obliged to perform Yibum.