Which three questions did Yaakov tell the messengers Eisav would ask them?
Rashi: The three questions were - (a) 'To whom 1 do you belong (i.e. who sent you)?; (b) 'Where are you going?'; (c) 'To whom do these animals belong (i.e. to whom are they being sent)?'
Because a 'Lamed' in front of a word is equivalent to 'Shel' (belonging to [whom]).
What is the significance of the four times ?Gam? in the Pasuk?
Ba?al ha?Turim: It hints at the four Galuyos - Bavel, Paras and Madai, Yavan and Edom.
Why does it say "Leimor" regarding Eisav?
Ohr ha'Chayim #1: Even if he does not ask in exactly these words (give these answers).
Ohr ha'Chayim #2: Even if he does not ask you himself, rather, through an intermediary (give these answers).
Why did Yaakov command the first messengers to answer Eisav only if he asks?
Malbim: He wanted Eisav to think that Yaakov is going to Se'ir, and the gift is going to there.
Why does it say, "Eisav Achi"? Before, Yaakov said, "Adoni" (32:5)!
Ha'amek Davar: He is my brother, and loves to investigate what he sees. Surely, he will ask you!
Why would Eisav ask, "where will you go?", and not, 'where are you going?' Why did Yaakov not give an answer to this question?
Ha'amek Davar: He told them, even though you see Eisav continuing on his way, also they should go and not return; Eisav should understand this. Yaakov said, "take my gift... that was brought to you" (33:11). I.e. he cannot take it now; for the messengers brought it to Sedeh Edom.
QUESTIONS ON RASHI
Rashi writes: "'L'Mi Atah' - To whom do you belong; i.e. who sent you?" Why does Rashi explain this way?
Gur Aryeh: We cannot explain the prefix Lamed in the usual sense of 'to' - i.e. 'to whom are you going' - for they were to answer, "l'Avdecha, l'Yaakov" (32:19)! Rather, it must mean, "to whom do you belong."
Rashi writes: To whom do you belong; i.e. who sent you?" What does Rashi add this explanation?
Gur Aryeh: People do not normally ask a passing worker or slave, 'To whom do you belong,' as it is none of their business. But a large tribute passing by is unusual, and it causes people to ask as to who sent it.
Rashi writes: "'ul'Mi Eleh Lefanecha' - These [animals] before you, whose are they? To whom are they being sent?" Why does Rashi explain this way?
Gur Aryeh: It cannot mean 'to whom do they belong [presently],' for that was already the first question ('who sent you'). It must mean, "for whom are they."
