What entered Yehudah's head? Does a Tzadik like him seek intimacy with a Zonah?
Seforno: Yehudah's actions were initiated by Hashem, who wanted Yehudah, who was more perfect than his son Shelah, to father Tamar's child, from whom Mashi'ach was destined to descend. 1
Hadar Zekenim (to 38:14): Because she covered her face, he did not recognize her. 2
Riva (to 38:15), Da'as Zekenim (to 38:17), Hadar Zekenim (to 38:17), Moshav Zekenim (to 38:18): An important person takes two men to accompany himself. He was Mekadesh her 3 in front of them. 4
Oznayim la'Torah (citing R. Moshe ha'Darshan): The Pasuk is speaking about Yehudah when he was going to celebrate the shearing of the sheep when it was customary to hold a big party 5 - and Yehudah was heavily drunk when he came across Tamar.
Gur Aryeh (to 38:15 and 38:18): A Kedeshah (harlot), that the Torah would later forbid (Devarim 23:18), is defined as someone that is Hefker, devoted to and constantly available for Zenus (Rashi to Devarim ibid). But Yehudah said to Tamar, "'Havah Na' - i.e., prepare yourself with intent for this purpose!" (see Rashi to this verse). Yehudah told her she should not be with him in Zenus, but rather, that she would be designated for him (alone). 6
Refer to 38:26:1:2. Rosh, Moshav Zekenim and Da'as Zekenim (to 38:15), citing Bereishis Rabah 84:9 - Hashem sent an angel to arouse his desire and force him (refer to 38:16:151:1). Why did Hashem bring kings and Nevi'im in such a lowly way? We appoint a leader only if his past is shady. Had Yehudah produced kings honorably, he would have become haughty over the other Shevatim!
Hadar Zekenim says that this answers the question, but it is not clear how. Perhaps words are missing, and he asked why he paid to do Yibum, as if it was Bi'ah with a harlot. (PF)
Kidushin does not take effect through a security! We can say that he gave her additional money for Kidushin. Da'as Zekenim, Hadar Zekenim - This does not help (for she intends for the security)! Rather, he was Makneh the security to her, and later stipulated that she send the security in exchange for a goat. Riva - ... or, he was Mekadesh through a document or Bi'ah. But Kidushin does not take effect on a daughter-in-law! Refer to 38:14:2.3:1 and the note there. Da'as Zekenim (to 38:26) - Before Matan Torah, Kidushin took effect on Arayos, e.g. two sisters, or one's aunt (Yocheved).
Witnesses must recognize the parties involved. If they recognized her, Yehudah could have given the goat, like he promised! Perhaps she showed them an extraordinary Siman that Yehudah did not notice, e.g. an extra joint in her pinky. PF)
Oznayim la'Torah: As we find for example, by Naval in Shmuel I 25:36; and by Avshalom in Shmuel II 13:23.
Gur Aryeh (Mechon Yerushalayim edition), Footnote 87: This is like the Ra'avad (Hilchos Ishus 1:4); she is a Pilegesh. (In what sense was she designated for him? He did not recognize her. After the Bi'ah, he went away, and sought her only to redeem the securities from her! - PF)
How could Tamar make herself Hefker to Yehudah? She knew that she was his daughter-in-law, and forbidden to him!
Gur Aryeh (to 38:15) #1: For Bnei Noach, the prohibition of a daughter-in-law ceases after the son dies.
Gur Aryeh (to 38:15) #2: According to Rashi (to Sotah 10a), Tamar's marriage to Er and Onan was mid'Rabanan, and she could do Mi'un, undoing her status as a daughter-in law. 1
Gur Aryeh (to 38:15) #3: Prior to Matan Torah, the concept of Yibum applied not only to the deceased's brother, but his father as well. The Mitzvah of Yibum pushed aside the prohibition of a daughter-in-law, just as the prohibition of a sister-in-law is pushed aside after Matan Torah. 2
Why did Tamar ask Yehudah for a token?
Why does it say "va'Yet"?
Bereishis Rabah (84:9): Hashem sent an angel to arouse his desire and force him. It says here "va'Yet," like it says "va'Tet" (Bamidbar 22:23) about Bil'am's donkey; an angel made it veer.
Ha'amek Davar: Yehudah veered away from Chirah, who had been accompanying him.
We already know that he did not know that it is Tamar! Why does the Torah repeat this?
Ha'amek Davar: Even after he spoke with her, he did not know [from her voice].
QUESTIONS ON RASHI
Rashi writes: "'Havah' - Prepare yourself with intent for this [purpose]!" What does this mean?
Gur Aryeh (to 38:15): Yehudah surely did not sin by living with her as a harlot; rather, he told her to prepare herself to be designated for him (only). 1 Refer to 38:16:1:5.
Prior to Matan Torah, (and for Bnei Noach), there is no concept of Kidushin; designation (Yichud) for one man is the equivalent of marriage. See Rambam and Ra'avad, Hilchos Ishus 1:1 and 1:4; and Hil. Melachim 9:8. (CS)