Deuteronomy 34:8

The Israelites wept for Moses in the plains of Moab thirty days. Then the days of weeping and mourning for Moses came to an end.

1 Samuel 1:10, 16

Deeply hurt, Hannah prayed to the LORD and wept with many tears. (16) “Don’t think of me as a wicked woman; I’ve been praying from the depth of my anguish and resentment.”

2 Samuel 18:33, 19:1b, 4

The king was deeply moved and went up to the chamber above the city gate and wept. As he walked, he cried, “My son Absalom! My son, my son Absalom! If only I had died instead of you, Absalom, my son, my son!” (19:1) It was reported to Joab, “The king is weeping. He’s mourning over Absalom.” (4) But the king covered his face and cried loudly, “My son Absalom! Absalom, my son, my son! ”

2 Samuel 12:16

David pleaded with God for the boy. He fasted, went home, and spent the night lying on the ground.

Matthew 26:38-39

He said to them, “I am deeply grieved to the point of death. Remain here and stay awake with me.” Going a little farther, he fell facedown and prayed, “My Father, if it is possible, let this cup pass from me. Yet not as I will, but as you will.”