A young man wanders alone in a distant field, his mind set on a single purpose. Despite the deep and bitter tensions that exist within his family, his search reveals a profound dedication to his siblings. He is simply looking for his brothers.
When sharing his mission with a stranger, it seems unusual that he expects the man to know who his family is without any further explanation. One perspective suggests that his family's shepherds were a regular and well-known presence in that specific region, making them easily recognizable to anyone passing by [ביאור יש״ר]. Another possibility is that the young man assumed the stranger already knew him and his family. This fits with the idea that the stranger was actually an angel, as angels of God were frequent and familiar visitors in the homes of his ancestors [ברכת אשר על התורה]. On the other hand, it is also highly likely that he did not rely on the man knowing them at all, but rather provided a physical description of his brothers so the stranger could identify them [ביאור שטיינזלץ].
The reason he so readily asks the stranger for information stems from the way the man first approached him. The stranger did not merely ask what he was doing; he invited the young man to share what he was missing, strongly hinting that he could help him find it. Because of this welcoming approach, the young man naturally asks for his assistance [אור החיים]. When asking for their location, his request is generally understood as a polite and conditional one, essentially meaning that the man should only tell him if he actually knows where they are [אבן עזרא, רד״ק, מחוקקי יהודה ויהל אור]. Other commentators focus on the geographical nature of the inquiry, suggesting he was asking for the specific part of the region they were occupying [ספורנו], or whether the stranger had seen them moving their flocks to a completely different field [ביאור יש״ר].
Within this search lies a quiet tragedy. Moving an entire flock of sheep to a distant and unfamiliar pasture is not a normal occurrence. Once he learns that his brothers have completely left the area for a faraway location, he should have immediately suspected a trap. However, he ignores the clear warning signs and continues to follow them, driven by a heart that still views them as his beloved brothers [מלבי״ם].