The entire back-and-forth between Bilaam and the angels is very difficult to comprehend. Initially, when Balak’s representatives came to invite Bilaam to curse the Jews, Hashem said to Bilaam in no uncertain terms (22:12): lo seilech imahem – do not go with them.

When Balak followed-up by sending higher-ranking officers, Hashem relented and explicitly permitted Bilaam to go with them (22:20), which he indeed did the following morning. Curiously, the very next verse states that Hashem was angry with him for going. Why did Hashem change his position regarding the permissibility of going with Balak’s agents, and why did he get upset when Bilaam merely followed His instructions?
A number of commentators (the Vilna Gaon, Malbim, and Tosefes Bracha) beautifully note that there are two words in the Hebrew language

which mean “with them” – imahem and itam. As every subtle difference is loading with meaning, they explain that while both words mean “with them,” the word imahem is used to refer to a case in which one is completely identical “to them,” while itam is appropriate for a case in which one is similar, but not identical, “to them.”
We may now understand that the agents of Balak wished Bilaam to go with them not just physically but in kindred spirit, united in their plan to curse and destroy the Jewish nation.

Not surprisingly, Hashem replied lo seilech imahem – you may not go together with them in an identical fashion, one in which you share the same motives that they do. When Hashem subsequently appeared to relent, it was with one crucial condition: kum leich itam – you may walk together with them, but not united with them in your intentions, as Hashem explicitly permitted him to say only what He would command him. Bilaam, with his intense hatred for the Jews, refused to accept this subtle, but critical, distinction, and the Torah relates that vayeilech im sarei Bilaam – united with them in their mission, and it was precisely at that moment that Hashem got angry at his refusal to follow directions!
We may now answer another difficulty with this understanding. When the angel subsequently gives Bilaam permission to go with the men, Rashi comments (22:35) b’derech she’adam rotzeh leilech molichin oso – a person is led in the direction in which he truly wishes to go, so in this case Bilaam was given permission to go with Balak’s agents for the purpose of cursing the Jews. Why didn’t Rashi write this comment when Hashem previously allowed him to go with these men?

The Gaon explains that until now, he was permitted only to walk with them, but not united with them in their intentions.

At this point, the angel said to him leich im ha’anashim, thereby giving him permission for the first time to join them in their diabolical scheme, and it was precisely at this point that Rashi noted that Hashem permitted him to travel in the path he truly desired to go in!

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