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Rabbi DY Stern: Parashat Vayishlach 5786

3 December 2025 – 13 Kislev 5786 | Torah Commentary

Crossing the Narrow Bridge: Fear, Hope and the Path Forward

To what might the challenges in our lives be compared? Rebbe Nachman of Breslov suggests the image of crossing an extremely narrow bridge. It may be the safest path through a difficult moment, yet how easy it is to lose one’s balance and fall. He goes on to teach that in crossing such a bridge, as in life, the most important thing is not to succumb to fear. When we encounter pain, despair or hardship, the essential task is simply to keep moving forward.

In Parashat Vayishlach, Jacob faces his own narrow bridge: a long awaited encounter with his estranged brother, Esau.

Their conflict begins before birth. The Torah tells us that Jacob and Esau struggled even in the womb, causing their mother great pain. Our personal struggles are rarely contained within ourselves. They spill out, and others feel the impact.

As the brothers grow, the distance between them deepens. The episodes of the birthright and the blessing leave Esau feeling cheated, leading him to exclaim, “I will kill my brother Jacob!”

Jacob flees, and the brothers remain apart for many years.

Eventually, though, avoidance is no longer possible. Jacob understands that for his own sake, and for the sake of future generations, he and Esau must meet.

Vayishlach offers insight into both the emotional and practical dimensions of reconciliation. While Jacob takes precautionary steps to protect his family, his first act is to send messengers to Esau to gauge whether his brother is open to meeting. The messengers return saying, “We came to your brother Esau; he himself is coming to meet you, and his delegation numbers four hundred.”

Jacob is unsure how to interpret this. The 18th century Kabbalist Or haChaim reads the four hundred as armed men and proof of Esau’s evil intentions. Chizkuni, the 13th century commentator, instead sees Esau as coming toward Jacob happy to welcome him and with 400 diplomats in order to honour him.

Faced with uncertainty, Jacob prepares carefully. But he also recognises that real peace, and indeed inner calm, can only emerge through communication. Despite his fear, he continues to reach out.

And so, after a long process, the two families finally meet, embrace, and part peacefully.

If only all reconciliations were so simple.

Sometimes the rifts between people rest on genuine wounds. Yet the story reminds us that sustaining hope, seeking dialogue where possible, and refusing to be ruled by fear are all part of crossing the narrow bridges of our own lives.

The journey may be unsteady, but we keep going.

Shabbat shalom.

  • Rabbi DY Stern serves Radlett Reform Synagogue.