The Prayer Challenge

I have always struggled a bit with prayer - what form should it take, how to address God, what to say, what to ask for, what's the point, etc. I don't think that this is particularly unique for anyone who chooses to address God from time to time.
Several years ago, I decided that I would change the tone of my praying and the way that I addressed God. Rather than adopt a little me talking to the all-powerful God type of perspective, I would address God as more of a friend That was, after all, consistent with the more familiar relationship that I was looking to foster w/him. I would start my prayers w/something akin to "Hi God. What's up? Just checking in…" That worked for me for a while but in the end was a somewhat empty familiarity in that it was unfounded. It was like those guys that call you buddy when they barely know you. "How's it going buddy? Have I got a deal for you."
When the awareness that something was wrong in my body began about a year ago, my prayers took on a new urgent significance. As I was seeing different doctors and having various tests done, I would pray, at each step of the way, that God would grant me the best news/result at that particular juncture. So, it was that I was relieved when it wasn't a kidney problem; relieved when it wasn't a mysterious virus; relieved that it wasn't hepatitis. At every step, I could rest assured that my prayers might be getting answered in that whatever news I did get was the best at that point. Until, I was left with few "good" options of what it could be. [At one point I heard about a woman who had similar symptoms and ultimately found that she had an issue with her belly button. So, I prayed for the belly button option.] Even once the cancer was confirmed, there was little time or emotional space for spiritual accountability - there were critical medical decisions to be made. As it turned out, I now see that it just so happens that God came through at each crossroad and ultimately did give me the best news that he could.
Looking back on that progression and on my relationship with God since, I have consciously been trying to pray a little differently. Until now in my life, my prayer requests have been very general - that God be present or help out in a given situation, I left Him a lot of leeway. It was ultimately up to Him on what he was going to provide and how something was going to go down so I didn't get too specific in my requests. Being polite and non-demanding n my prayer requests was also very safe. By doing so, I wasn't holding God accountable and so I never had to confront him when/if he fell short of my needs or expectations.
Lately, I have been challenging myself to have a better (more intimate) relationship with God. I've been looking to up the ante for both of us. I've been trying to be specific in my prayer requests and then deal with the disappointment if those requests are (seemingly) denied. A setback merely invites another, albeit more difficult, conversation with him.
It is analogous to the choices we make in the way that we conduct our relationships with those near to us. My relationship with Jacquelyn would probably be much more sanguine if I made few or no specific requests of her, if I never asked her to fulfill my needs. But it is precisely in how we express our needs and then go about satisfying them for each other that is the basis of the love in our (any) relationship. The waters might be calmer in the absence of such exchanges but they wouldn't be very deep.
So, in seeking a deeper and healthier and more intimate relationship with God - and all of the important people in my life, really - I am putting my wants and needs out there. I am asking and then dealing with the potentially messy consequences. It may be a more difficult row to hoe but will, I trust, be far more fulfilling.