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So, the best question any pastor can be asked is "How can I learn to pray?" I know how I do it, but what resources (preferably in Scripture, although classic works are acceptable) would be useful for actually guiding someone in developing a disciplined prayer life?

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some people think they have to pray in a weird formal language, they really have no idea what to do. At my church the pastor requests that we pray in very simple terms (like we are talking to a person in front of us) and from the bottom for your heart...followed by a brief time of silence. –  Greg McNulty Apr 11 '12 at 0:45

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In Acts 4, after being arrested and subsequently released by the Council of Pharisees, Peter and John lead "their friends" in prayer:

24 And when they heard it, they lifted their voices together to God and said, “Sovereign Lord, who made the heaven and the earth and the sea and everything in them, 25 who through the mouth of our father David, your servant, said by the Holy Spirit,

“‘Why did the Gentiles rage,
     and the peoples plot in vain? 26 The kings of the earth set themselves,
     and the rulers were gathered together,
     against the Lord and against his Anointed’

— 27 for truly in this city there were gathered together against your holy servant Jesus, whom you anointed, both Herod and Pontius Pilate, along with the Gentiles and the peoples of Israel, 28 to do whatever your hand and your plan had predestined to take place. 29 And now, Lord, look upon their threats and grant to your servants to continue to speak your word with all boldness, 30 while you stretch out your hand to heal, and signs and wonders are performed through the name of your holy servant Jesus.” 31 And when they had prayed, the place in which they were gathered together was shaken, and they were all filled with the Holy Spirit and continued to speak the word of God with boldness.

Several things can be noted from this prayer.

  1. They immediately address God as "Sovereign Lord". They acknowledge his power and knowledge, but most importantly his status as King over his people.
  2. They go on to praise God for his works of creation ("heaven and earth and the sea")
  3. They quote Scripture in the prayer - scripture that they use to reinforce their later plea
  4. They reason with God. They say "you yourself say, why did the Gentiles rage? Look! They're raging now, they raged against Jesus! Show your power, protect us, enable us to keep preaching your word"
  5. It's gospel-centric. At the core of their prayer is "your holy servant Jesus, whom you anointed."
  6. Their goal is not physical well-being, but the proclamation of the gospel. They say "look upon their threats and grant to your servants to continue to speak your word will all boldness." They don't ask for protection - all they care about is preaching the word of God.
  7. It was a pretty darn good prayer. The Holy Spirit shook the place! It was an edifying prayer - the Holy Spirit filled them and they continued in their goal to preach the word of God.

I expounded on this on because I find it a very good prayer, but there are plenty of others. It's a good rule of thumb, in my opinion, to take the prayers of the saints as templates. Peter and John were apostles - they asked Jesus how to pray - and they learned well!

Our church's Assistant Pastor preached a series on prayers of the bible once. Here's some of the passages he preached on:

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Many of the Psalms are simple expressions of prayer. They exhibit a wide range of emotions, including despair, anguish, pain, hope, rejoicing, faith, anger, and worship. Our relationship with God should allow us to voice these emotions much like the psalmists did.

Of course, the Lord's prayer in Matthew 6:9-13 is an obvious pattern, but also David's prayer in 2 Samuel 7 and Jesus' own prayer in John 17.

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