What does Genesis 37:29 mean?
After securing Joseph in the pit, Reuben seems not to have stayed to eat with his brothers (Genesis 37:18–25). He seems to have missed the exchange recorded in the last few verses, in which Judah talked his brothers into selling Joseph as a slave to passing traders (Genesis 37:26–28).When Reuben returns to check on Joseph—perhaps to free him and return him to their father—he finds the pit empty. Heartbroken, Reuben tears his clothes in a sign of grief. Unlike the modern era, where people often see clothes as disposable, garments in the ancient world were meant to last. Tearing one's clothes was both an act of sacrifice and a clearly visible sign of mourning. Reuben is deeply upset by what has happened.
Depending on his motives for rescuing Joseph, this might be selfish grief. It's possible Reuben saw rescuing Joseph as a way of redeeming himself, after defiling the family by sleeping with his father's concubine (Genesis 35:22). Now that opportunity is lost (Genesis 37:30).