Let's do this in chunks. I could write all day but the reality is that you probably don't have time to read all day. I'll keep it short and to the point and each day we'll build on the previous day until we feel like we've arrived at some semblance of an answer to this question.
"Pastor Andy, can you give some insight to those looking for a way to start praying, if they haven't ever felt like prayer is a strong point for them?" This was a question I received recently and wanted to take some time to dig into it a little bit. I think when answering this question you have to start at the ground floor and then begin to work your way up. The foundation of a great prayer life begins with authenticity. When we communicate with God we're getting the "real deal" from Him. God doesn't have to strive to be real, He's never tempted to put on a false front, but from time to time, we are. Sometimes we buy into this thought that we need to "get things together" before we bring ourselves to God. Here's a newsflash, God already knows that we're a mess. As I read the question that came in, particularly the part that said, "...if they haven't ever felt like prayer is a strong point for them..." I was struck by the thought that perhaps what prohibits people from feeling as though prayer isn't a "strong point" is fear. Fear that we're not good enough to talk to God. Fear that He isn't listening because it's been a while since we last spoke with Him.
We don't need to fear when we come to God in prayer. He longs for an authentic intimate relationship with us and since we know that He's already bring His "realness" to the equation, all that's left is for us to bring our "realness". Romans 8:15 communicates this truth, "For you have not received a spirit leading to fear again, but you have received a spirit of adoption as sons by which we cry out, "Abba Father!" It may be difficult for you to make this jump if your earthly father wasn't in the mix and providing a strong example, but nevertheless that Scripture is clear that God desires we come to him as child would to a father. Not in fear, not trembling, not convinced of His anger toward us. We are called to come knowing that He loves us, He cares about every need and He desires to bless us. When you come to God, come just as you are. Bring your garbage. Bring your struggles. Bring your questions. Bring your doubts. Bring your "real self".