When the brothers were united with Joseph, the verse says: “Benjamin cried on Joseph’s shoulder, and Joseph cried on Benjamin’s shoulders.”
The Medrash takes note of the switch from singular to plural. Why singular for Joseph’s shoulder and plural for Benjamin’s? The Medrash explains that this was foreshadowing a later period in Jewish history. Hundreds of years later the Mishkan Tabernacle would be in Shilo, in Joseph’s territory in the land of Israel. After that, two Jerusalem Temples would be built and destroyed in the portion of Benjamin. Joseph cried for Benjamin’s dual loss (the two Temples) and Benjamin cried for Joseph’s loss of Shilo.
Hey, but why didn’t they cry or mourn for their own losses?
The Lubavitcher Rebbe explains: We don’t cry for our problems. If its our issue, and within our control, we can’t cry. We must do something about it. Better one action than a thousand sighs. But for other people’s issues, if we tried to help them and its beyond our control, then crying and feeling with them is appropriate and laudable.