go, do. reconcile part 1

To my seemingly best ability, i am trying to live by a godly standard. (Standard DOESN'T have to imply negativity or obligation) A new way that i have been trying this out is meeting new people, OR, better yet, meeting the people i kind of interact with, yet do not know well enough to feel obligated to converse with. Example: Almost anyone in any service industry- yes they are my server and they have to be nice to me while they make my coffee, but they are needing real interaction as i do. Example: My back yard neighbor. Me and my friend sara decided it would be a great idea to sleep outside last weekend, no tent, just blankets and mosquito spray. Ironically, my backyard neighbor decided to have a bonfire with some friends. Sara and i were too lazy to make our own fire that night, but i did go and buy smore stuff in case a fire occurred, so, after psyching myself up for 15 minutes, i walked over there with my bag of smore stuff and just gave it to them, and they were very grateful, and we ended up joining them for an hour. But in order for me to go over there, i LITERALLY had to ask sara, "okay, whats the worst case senario if i go over there to give them this food?" Why? Why whould i be so hesitant to do something nice? Why do i sometimes avoid eye contact with random people i recognise from high school?
I'm going through a phase where i would rather go and do than sit and wait for people to interact with me. I'm thinking that this may be spurred on from the fact that for the last 2 months, i feel like i keep running into very random people from high school in very random places. I think it's also from my observation of the people Christ was focussing his attention on while he was on earth. Of course we READ he was with lost sinners; tax collectors, the poor, lowly citizens, but, at least for me, i get this Monty Python and the Holy Grail-ish/Life of Brian imagery of dirty people with the creepy cackle when i think of the crowd he preached to. I have only recently thunk (i know) to modernize this imagery.
I have come to recognise that, if i'm aloud to pick out a "people group" that i care for and hope "bring to the understanding of Christ" (ugh, cliche) it would be the ones who have been "churched" their whole lives and yet feel like there are too many unanswered questions for "christianity" to be worth betting a soul on: The people who are extremly interested in talking about religion and life, yet, are 1) too old for youth group or drop in centres 2) too uncommited to christianity to join a "college and career/young adults" church group thing, or 3) too frustrated or stubborn with the idea of going to church as a whole. Of course, some people (myself included) use these 3 situations as an excuse not to try any venues. I didn't have any desire to go to church for 5 years, under of the "too stubborn and disagree with church" excuse, until a co-worker at the time/christian challenged me by saying that my protest towards "the dumb way church is" by simply not going was accomplishing nothing, that if i saw a need for change, i should stop my complaining and start going to a church so i can start implementing change.
Well, duh. Shut up and do something about it if it bothers you so much.