Summary: Several Scriptures in the Gospels record Jesus weeping. Two showed His heartfelt love for groups of people. A third showed that His love extends to you as an individual.
Luke 13:34-35a “O Jerusalem, Jerusalem, you who kill the prophets and stone those sent to you, how often I have longed to gather your children together, as a hen gathers her chicks under her wings, but you were not willing! [35a] Look, your house is left to you desolate.”
Luke 19:41-42 As he approached Jerusalem and saw the city, [Jesus] wept over it  and said, “If you, even you, had only known on this day what would bring you peace — but now it is hidden from your eyes.
•• These two instances where Jesus wept reveal to us how deeply Jesus’ heart was (and is) moved by the plight of people who choose to reject Him. Both while en route to Jerusalem (Luke 13) and then overlooking the city of Jerusalem and its thousands of residents (Luke 19), Jesus’ heart was deeply saddened by the failure of the majority to receive Him.
• “O Jerusalem, Jerusalem...”
• “How often I have longed to gather [you]...”
• “You were not willing ... [and are] left...desolate.”
• “[Jesus] wept over it” on one occasion.
• “If you ... had only known ... what would bring you peace.”
•• I personally feel a sense of conviction when reading these verses. Am I moved to tears as I look around and see people rejecting the free gift of life in Christ? Ask yourself: Are you brought to the point of weeping over lost souls? The Savior was. We see Jesus crying as He pondered the pending condemnation of those who chose to resist His gracious words.
•• Jesus was moved to tears by the faithlessness and hardness of heart of the majority of the population of an entire city, Jerusalem. Ponder that. Allow the Holy Spirit to place into your heart a burden for the lost souls of your city.
•• Jesus is the same yesterday and today and forever (Hebrews 13:8). Today, in your city, your town, your community, I can visualize Him weeping over many people’s resistance to Him and His gracious offer of forgiveness and eternal life. Ask Him to plant in your heart a sense of His sorrow over lost souls. And allow that to energize and increase your efforts to be effective witnesses for Him.
John 11:32-36, 39, 43-44 When Mary reached the place where Jesus was and saw him, she fell at his feet and said, “Lord, if you had been here, my brother would not have died.”  When Jesus saw her weeping, and the Jews who had come along with her also weeping, he was deeply moved in spirit and troubled.  “Where have you laid him?” he asked. “Come and see, Lord,” they replied.  Jesus wept.  Then the Jews said, “See how he loved him!” ...  “Take away the stone,” he said...  Jesus called in a loud voice, “Lazarus, come out!”  The dead man came out, his hands and feet wrapped with strips of linen, and a cloth around his face. Jesus said to them, “Take off the grave clothes and let him go.”
•• In this second instance we see that Jesus cried over the plight of an individual. The importance of this, as I see it, is to show that not only is Jesus concerned with reaching the world at large with the Gospel of His grace. He is also vitally concerned with the life and needs of each person.
•• Lazarus was dead, and Jesus was “deeply moved”. The onlookers noted His sorrow and commented: “See how He loved him.”
•• The Lord plays no favorites. As in the case of Lazarus, Jesus is “troubled” and “moved” by your needs — your health issues, your financial struggles, your emotional captivities, your spiritual shortcomings, and much more.
•• Come boldly to His “throne of grace ... to find grace to help [you] in time of need” (Hebrews 4:16). Remember how Jesus wept at Lazarus’s tomb. He is similarly “touched with the feeling of our infirmities”, our weaknesses (Hebrews 4:15).
•• Don’t ever feel that you are “imposing” upon Jesus when you come to Him with your needs. He is touched by your weaknesses. He loves you deeply as an individual, not just as part of a larger group. He was moved to tears by the sad plight of one man, Lazarus. He is the same today, and His heart is touched by your needs. Come to Him humbly, yet confidently, knowing that He loves you and is “deeply moved” to help you.
In sum, the Gospels record several instances where Jesus wept:
1) Once as He was traveling towards Jerusalem, and then again as He was approaching Jerusalem. In both instances He was tearfully lamenting the lost condition of the people as a whole.
2) And at Lazarus’s tomb, Jesus wept over the death of one, solitary individual.
•• For those who have wondered why Jesus wept, the message is clear — Jesus’ heart is moved for the world at large, as well as for you and every individual in it. How blessed we are to have a Savior who is “touched with the feeling of our infirmities” (Hebrews 4:15).