בראשית, פרק כ״ח, פסוק ח׳

Esau’s delayed awakening regarding his marriages occurs against the backdrop of his brother's departure for Haran. Only after observing his father's strict instructions to Jacob does Esau finally grasp the profound distaste his family holds for Canaanite women. Commentators offer several explanations for why this realization dawns on him so late. It is possible that Esau previously assumed only his mother opposed his marriages, and he is just now exposed to his father's firm stance [ביאור שטיינזלץ]. Alternatively, his mother might have kept her complaints private, sharing them only with her husband, leaving Esau unaware until he overheard the public command given to Jacob [ברכת אשר על התורה]. Another perspective suggests that Esau already knew his marriages displeased his father. However, because his father never strongly protested or demanded that he annul them, Esau dismissed the issue. His father had refrained from confronting him, knowing that Esau was not destined to continue the family's spiritual lineage. Yet, when Esau sees the great lengths to which his father goes—sending Jacob all the way to Padan Aram simply to avoid a Canaanite marriage—he finally understands the true gravity of the matter [רד״ק]. This dynamic implies that had his father been more attentive and protested earlier, he might have successfully prevented Esau from marrying Canaanite women in the first place [ספורנו].

Interestingly, the narrative focuses solely on the fact that these women were displeasing to his father, completely omitting his mother, even though she had previously expressed utter despair over her life because of them. This omission stems from Esau's deep resentment toward his mother for her role in transferring the blessings to Jacob. Consequently, he entirely ignored her opinions and her displeasure [ביאור יש״ר, ברכת אשר על התורה]. Beyond the metaphorical understanding of the women being displeasing in his father's eyes, some interpret this detail quite literally. The wickedness of the Canaanite women caused actual physical harm to his father's eyes. Because they burned incense for idol worship, the resulting smoke entered his eyes and ultimately caused his blindness [שפתי כהן].

Esau's reaction to this newfound awareness reveals much about his character and underlying motives. His realization that the Canaanite women were bad did not stem from a moral awakening about their corrupt behavior. Rather, he only cared that their actions went against his father's will and provoked his strictness [ספורנו, אור החיים]. While he may have genuinely wanted to please his father without needing a direct command [העמק דבר], his true motivation might have been self-preservation. Fearing that the blessings he had received would be nullified if his descendants were born exclusively to Canaanite women, he rushed to marry into Ishmael's family to secure those blessings through her children [אור החיים].

Ultimately, Esau's attempt to correct his mistake only highlights his deep flaws. Although he recognized the problem, his solution was entirely inadequate. He neither divorced his Canaanite wives nor sought a wife from Laban's family, as Jacob was commanded to do. Instead, he went to Ishmael and simply added another wife to his existing household. By choosing a woman from a family that also carried spiritual deficiencies, he failed to fix the core issue, merely compounding his previous sins instead of resolving them [מלבי״ם, אור החיים].