The sages viewed the encounter between Jacob and Esau as a guidebook to dealing with our enemies. Three major lessons that are emphasized are the need for: prayer; gifts; and preparedness for battle.  I would humbly like to add one more lesson: be aware of the ambiguity of motivation.

“And Esau ran to greet him. And he embraced him and he fell upon his neck and kissed him and they cried” (33:3).

When reading from a Sefer Torah one sees that the word for “and he kissed him” has dots over all six of its letters. Rashi quotes a midrash from the Sifrei that there is a disagreement regarding the proper interpretation of the dots. Some say that it means Esau did not kiss Jacob with all of his heart—i.e. he still retained a certain amount of hatred towards his brother. Rabbi Shimon ben Yochai said: It is a fact (the word halakha is used in the Hebrew) that Esau hates Jacob, but his compassion was aroused at that moment and he kissed him with all of his heart.

In other words, are the dots meant as emphasis—he really kissed him; or as scare quotes—he “kissed” him. Emphasis, or irony? This lack of certainty regarding the message of the scribal technique perhaps mirrors the uncertainty of Jacob. Is Esau sincere, or is he putting on a show? It also reflects a deep uncertainty the reader has regarding Esau.

Earlier, the text says (25:28) that Isaac loved Esau “ki tzayid b’piv.” The literal translation is “for the game was in his mouth”—what Esau had trapped in his hunting excursions was in Isaac’s mouth. In other words, Isaac loved Esau because of what he put in his mouth. Rashi cites a midrashic reading that the game/trap was in Esau’s mouth—meaning, he would trap/trick his father with his own mouth and deceive him. We are left wondering was Esau deceptive or sincere?