My bow isn't pink, it's not even tied

I'm reading this book called My Beautiful Idol by Pete Gall. Daryl recommended it to me, turns out he has only read like 5 pages....good think it's an excellent book.
One of the earliest chapters has me thinking about how we rank prayer requests, sin, and our struggles and concerns. How deep is deep enough, how superficial does the issue have to be for it to be a frivolous request? It seems they're ranked somehow and I can't figure out how. Pete had a conversation with his roommate Stephen who is a worship leader at a Colorado church, and he is gay.
For example (from Pete Gall):

This morning I stood in a circle holding hands with the other people from the praise band, doing prayer requests. The pastor's wife asked for prayer for her kids. She said they have such rebellious spirits. The kids are two and three years old!
...
I'm not making this up! Being the pastor's wife, she's pretty guarded, I'll admit. But the next person asked for prayer about the minivan he and his wife are thinking about buying. He said they wanted to honor God with their choice...Honor God with a minivan choice? Come on! Is this really the pressing issue in his life- the one that's so overwhelming he needs to call in prayer reinforcements?

Pete replies that Stephen shouldn't be so quick to critique other's prayers to closely, to which Stephen replied:

Would you have shared your prayer requests with them? Would have risked talking about not being sure about what you're doing with your life?

Pete replies that he's not sure but probably, he asks Stephen why not...

Here's my prayer request: I went to counseling Friday after work and prayed for freedom from my sins there. Again. For like the millionth time. I cried myself to sleep that night, half-drunk. I took a walk with Corey yesterday and told him that I couldn't see him anymore because I believed that what we're doing is wrong. Which means that I must think he was wrong when he made the choice to leave his wife and kids, and so is the hope he's had for his future with me. I came home, got drunk, and spent the evening alone with my stash of porn, feeling like I'm the only person in the world still fighting this batter- everyone in the gay community thinks it's leftover garbage from a repressed society of mutilators. The closest I came to telling anyone at church about it was when someone noticed I was chewing a piece of gum0 which you're not supposed to do on stage, but I was chewing it to cover up my alcohol breath- and she asked if I had an extra piece and winked at our shared wickedness when I gave her one. What do they teach you in seminary about sharing my kind of prayer request? Would you share that one? I'd be kicked off the praise team immediately because my sin disqualifies me from worshiping God. Rebellious toddlers and minivan selection- those things are good to take to God and are clean enough to keep a microphone in your hand- but I'd lose the one thread of connection I still feel to this deaf God who won't answer my prayers! My gay issues may not be my definition, and they may not be the bottom of my sin, but you can go to hell if you think I want to go deeper, or if you think it's something that I can carry with me into church, as a matter of fact. I know what it would cost me. Look at what it already costs me!

Wow. What do you do with that? How can you tell someone that it's ok to bring those struggles that are so raw to a body of believers when their experience and the experience of so many tells them it's not? I don't even want this to be about a gay issue per se. I mean in general, the messiness, the porn, promiscuity, drugs, alcohol, adultery, masturbation, self loathing, disbelief and serious serious doubts that God is even real anymore. How do you tell people that it's ok to bring that to a believer and that they won't get some pat answer about how all things are possible through the God that strengthens them. I mean, that scripture is true, but sometimes to people that are drowning in the reality of their life, of their sin, of their struggle they are just words. Jesus, while very very real, is not a physical body to cling to in the middle of the night when it seems impossible to even inhale one more time.
Life is messy, it's ugly, it's downright gross sometimes. How can I as a believer shine any light if I'm not willing to get my shoes dirty, my clothing torn, my hair messed up? How can you?
Not everything is fine. Everything doesn't always work out for the good. People die, they cheat, they murder, they lie. Is that a reason to never reach out to anyone ever again?

I used to think yes. But the conversations of late that I've had tell me, in all their brokenness, in all their damaged darkness, that the answer is really no. I mess up all the time. I suck a life sometimes. But in all of my flaws, in all of my shortcomings, I'm sometimes the only Jesus a person can see, and that makes getting down in the muck and hearing what is true all the more worth it.
We all know that our lives, that our struggles and relationships are not all in neat, pretty boxes and tied up with a pink bow. Why then do we keep expecting others to be the that way?