A lot of people ask me when they should Pray. I tend to answer with 1 Thessalonians 5:17, that they should "pray without ceasing."
Now, clearly it's not possible to spend every waking minute in prayer, but I do believe God was instructing us to pray as often as possible, to say "Thank You, God," whenever something good happens to us, and to stay in constant conversation with Him throughout our days.
So when should you pray? Always.
When to Pray
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