What made Yehudah assume that she was a Zonah?
Rashi #1: Because otherwise, what she was doing sitting at the cross-roads?
Ba'al Ha'Turim, Malbim: In lands of Yishma'el, the custom is to burn a letter on the face of harlots, so people will know that she is a harlot. They cover their faces so the letter will not be seen. 1 Later, Yehudah commanded to burn [a letter on the face of] Tamar.
Ba'al ha'Turim, Malbim: That is what Yehudah meant when he said "Hotzi'u'ha v'Sisaref" (38:24) - 'Burn a mark on her forehead!' See Torah Temimah, note 25, who presents a source for this explanation.
Why did Yehudah not recognize Tamar?
Rashi #1, Rashbam, and Targum Onkelos: Because her face was covered [at the present time]. 1
Rashi #2 and Targum Yonasan: Because when she lived in his house, she had always covered her face (out of modesty 2 ), so there was no way that he could have known who she was. 3
Seforno: Refer to 38:16:1:1 .
See Ramban, who elaborates on this explanation. Ha'amek Davar - Because he did not recognize her from afar, and assumed that she is a Zonah, he did not recognize her through her voice.
Sotah 10b: To teach us that 'A daughter-in-law who is modest in the house of her father-in-law, merits that kings and prophets will descend from her'. See Torah Temimah, note 19.
Tamar would be the last person he would expect to do so! See 38:15:2.1:2.
Why did Yehudah not recognize Tamar through her voice?
Ha'amek Davar: Because he did not recognize her from afar, and assumed that she was a Zonah, he did not recognize her voice even when he talked to her directly.
QUESTIONS ON RASHI
Rashi writes: "'For she covered her face' - ... Our Rabbis interpret, for she had covered her face while in her father-in law's house; she was modest...." Why does Rashi cite the Midrash?
Gur Aryeh: Were it to mean only that she had covered her face now, we already know this from the word "va'Tis'alaf" in the preceding Pasuk (38:14), which Rashi interpreted to mean that she concealed her face.
Sifsei Chachamim, Oznayim la'Torah: Even if her face was covered initially, he should have recognized her as Tamar upon speaking to her; and she surely uncovered her face prior to relations. 1 Rather, because Tamar had been so modest in his home, he did not suspect that this was actually her.
Rashi writes: "... For she had covered her face while in her father-in law's house; she was modest." What did Tamar merit as a result of her modesty?
Maharal (Chidushei Agados Vol. 2, p. 42, to Sotah 10b): The Gemara says that Tamar merited to be the ancestress of kings and prophets. Modesty is sanctifying oneself against indecency, a trait that transcends the physical. So too would her descendants merit G-dly distinction.