What were the answers to the three questions in the preceding Pasuk (refer to 32:18:1:1)?
Rashi: The answers were - (a) '[We were sent by] your servant Yaakov;' (b) (c) 'It is a gift being sent to my master Esav.' 1
Riva: The three answers were - (a) 'To your servant Yaakov;' (b) 'It is a gift being sent to my master Esav;' (c) 'The sender, of whom you said "in front of you" (32:18) - he is not; rather 'he is in back of us!' 2
Ohr ha'Chayim: (a) 'To your servant Yaakov;' (b) "Minchah Hi Sheluchah" (we are going to give a gift); (c) 'To my master, Esav.'
The responses followed the order of the questions (Rashi). Riva disagrees, for if so, there is no answer to the second question! Refer to 32:19:1:2. Ha'amek Davar also noted this, refer to 32:18:154:1.
Our text of Riva says, "in back of you;" but it seems that this is a mistake. Tosfos ha'Shalem (18:6) says similarly, and concludes "in back of us." (PF)
Why is the word "to" repeated, in the phrase, "[belonging] to your servant, to Yaakov"?
Gur Aryeh (to 32:7): This implies 'your absolute servant (without conditions), whose name is Yaakov.' 1
I.e., he is inherently a servant; the name merely comes to clarify who is speaking. But 'to your servant Yaakov' would mean Yaakov is independent; not inherently a servant. (EK)
Why is the word "to" repeated, in the phrase, "[being sent] to my master, to Esav"?
Gur Aryeh (to 32:7): He was flattering Esav, by implying, 'my absolute master (without conditions), whose name is Esav.' 1
I.e. Esav is his generic master; the name merely comes to clarify who is being spoken about. But 'to my master Esav' would mean he is a master, yet not excluding the possibility of other masters as well.
QUESTIONS ON RASHI
Rashi writes: "'Behold, also he' - [i.e.] Yaakov - is behind us." But right behind flock number one was not Yaakov, but rather flock number two?
Gur Aryeh: The pronoun "he" must be referring to someone already mentioned (and the first messenger made no mention of a second gift).
Rashi writes: "'Behold, also he' - [i.e.] Yaakov - is behind us." But verse 32:21 will state this explicitly?
Gur Aryeh: Even so, the latter verse repeats this, in order to add, "... for he said, I shall appease [Esav's] countenance, etc." (32:21) - all of which the shepherds were to say to Esav as well. 1
Refer to 32:21:2.1:2.