"Rejoice with those who rejoice; mourn with those who mourn." Romans 12:15

"Praise be to the God and Father of our Lord Jesus Christ, the Father of compassion and God of all comfort, who comforts us in all our troubles, so that we can comfort those in any trouble with the comfort we ourselves have received from God." 2 Cor. 1:3 & 4

"The sacrifices of God are a broken spirit; a broken and contrite heart, O God, you will not despise." Psalm 51:17

Ask God for His heart for others, He will allow you for a time to feel another's pain and to feel His heart.
Cry out for a spirit of conviction of sin, righteousness and judgment to come, a revelation of this, a lighting of the Holy Spirit upon the preaching of the Word of God.

There are many scriptural examples of this type of prayer:

"I am worn out from groaning; all night long I flood my bed with weeping and drench my couch with tears" Psalm 6:6.

"Be merciful to me, O Lord, for I am in distress; my eyes grow weak with sorrow, my soul and my body with grief" Psalm 31:9.

"Oh, that my head were a spring of water and my eyes a fountain of tears!  I would weep day and night for the slain of my people" Jeremiah 9:1.

"Jesus wept" John 11:35.

"As he approached Jerusalem and saw the city, he wept over it" Luke 19:41

"Then he said to them, 'My soul is overwhelmed with sorrow to the point of death.  Stay here and keep watch with me" Matt. 26:38

Other verses that refer to compassion and weeping:
Acts 20:19,31
2 Cor. 2:4
2 Cor. 7:5-7
Philippians 2:27
Lamentations 1:2; 2:18-19
Isaiah 62:6 & 7

Sorrow is one of the fruits of wisdom; "For with much wisdom comes much sorrow; the more knowledge, the more grief" Ecclesiastes 1:18.  The more you get apprehended with a vision of what God wants to do, and the more you have a knowledge of the Lord Jesus Christ, the bigger a gap you see of where you are and where He is, and where the body of Christ currently is, and where He wants to take us.  And it can create within you, if you'll let it, a heart smitten with compassion and brokenness.  That is an expression of sorrow.

The prayer of tears is an expression of having humbled yourself before God: "Grieve, mourn and wail.  Change your laughter to mourning and your joy to gloom.  Humble yourselves before the Lord, and he will lift you up" James 4:9 & 10.

Emotions are a vital part of prayer:

"Streams of tears flow from my eyes, for your law is not obeyed" Psalm 119:136.

".........I saw the tears of the oppressed -- and they have no comforter; power was on the side of their oppressors -- and they have no comforter" Ecclesiastes 4:1.

"Record my lament; list my tears on your scroll  --  are they not in your record?  Then my enemies will turn back when I call for help.  By this I will know that God is for me.  In God, whose word I praise, in the Lord,  whose word I praise  --  in God I trust; I will not be afraid.  What can man do to me?  I am under vows to you, O God; I will present my thank offerings to you.  For you have delivered me from death and my feet from stumbling, that I may walk before God in the light of life" Psalm 56:8-13

God's heart can change when He hears our cry:

"In those days Hezekiah became ill and was at the point of death.  The prophet Isaiah son of Amoz went to him and said, 'This is what the Lord says: Put your house in order, because you are going to die, you will not recover.'  Hezekiah turned his face to the wall and prayed to the Lord, 'Remember, O Lord, how I have walked before you faithfully and with wholehearted devotion and have done what is good in your eyes.'  And Hezekiah wept bitterly.  Before Isaiah had left the middle court, the word of the Lord came to him: 'God back and tell Hezekiah, the leader of my people, "This is what the Lord, the God of your father David, says: I have heard your prayer and seen your tears; I will heal you.  On the third day from now you will go up to the temple of the Lord.  I will add fifteen years to your life.  And I will deliver you and this city from the hand of the king of Assyria.  I will defend this city for my sake and for the sake of my servant David." 2 Kings 20:1-6

A great key to moving in the power of God is mercy:

"When Job's three friends, Eliphaz the Temanite, Bildad the Shuhite and Zophar the Naamathite, heard about all the troubles that had come upon him, they set out from their homes and met together by agreement to go and sympathize wit him and comfort him.  When they saw him from a distance, they could hardly recognize him; they began to weep aloud, and they tore their robes and sprinkled dust on their heads.  Then they sat on the ground with him for seven days and seven nights.  No one said a word to him, because they saw how great his suffering was" Job 2:11-14.

One of the best things we can do sometimes is not speak a word, and just weep over someone.  There's the prayer of tears that releases comfort.

There are different categories of tears:
 

• tears of gladness
• tears of repentance
• tears of grief
• tears of pain
• tears of intercession
• tears of sorrow

How do we weep with those who weep?  Discern the time and just do it.  Decide to share the pain.  Take the time to hear and to weep with other.  Don't always try to cheer them up and automatically offer solutions; "Like one who takes away a garment on a cold day, or like vinegar poured on soda, is on who sings songs to a heavy heart" Proverbs 25:20.

There's a time to cheerup, forgive and find the answer, but first weep with those who weep, take time to do this.  Be slow to say, "snap out of it right now in the name of Jesus."  Encourage people to talk about their situation and sometimes with specifics.  Sometimes venting is a part of healing and we must give time for someone to express their woundedness, their hurt, their anguish.  And even if we know their feelings aren't totally right, to let them express how they feel, but it can be a part of cleansing of the soul.  Be willing to wait in silence.  Be channels of compassion for God, because this expresses the love of God.  Then out of the place of waiting, don't assume sin automatically.  There's a place for clear, bold, gentle statements, but it takes time to achieve them.  Build a bridge called love to carry your truth over.  Incomplete forgiveness is better than none because you're making steps down the path.  Allowing time for the processing means you believe God is at work in them.  Then you enter into the prayer mode.  Pray for the person and ask the Holy Spirit to minister the promised comfort ("Blessed are those who mourn, for they will be comforted" Matt. 5:4; "But everyone who prophesies speaks to men for their strengthening, encouragement and comfort" 1 Cor. 14:3). After you've prayed the prophetic kicks in and comfort is ministered in truth.