My Story || What Is Important To Share?

Today was the first day for all of us summer interns here at Journey Church. Three of us started the day off by helping a couple in our church load up their things to move into their new house. Afterwards we all met up to grab lunch at Monical's and start discussing some things about the summer and how things would be working. We continued talking about summer plans at the office and talked some about how we go about reaching out to people in our community. 
Part of how we go about reaching out into our community is through intentional relationships. In order to build intentional relationships we have to plug ourselves into something or somewhere in the community. Sometimes this is by hanging out at a restaurant or coffee shop in the evenings for a couple hours and meeting someone there and starting up a conversation. Sometimes it is through going out and doing something like frisbee golf or volleyball. There are times when people just blow us off, but many times people don't. The whole point is for us to start building a relationship with them and eventually invite them to church and get them connected, hopefully to one day see them plugged in and developing a relationship with God. 
A big part of this process is talking with them and getting to know them and their story. Just like with every other relationship, we have to eventually share our story with them. I've shared my story with people before. I may have even posted a version on here at some point (if not I should probably change that soon). The thing is, at least from my perspective, it's hard to have one set "version" (if you will) of your story because you will more likely than not have to edit it or vary it for everyone you share with. Yet it is fairly easy to share a simple version with someone you're just getting to know.
Now my dilemma, is what version do I go with when sharing it with people who know me fairly well but haven't heard my whole story. I don't want to go super detailed, but I also don't want to do the outline version that just highlights key points. I also don't want to make it too uncomfortable for anyone or for myself. So at this point I'm wondering how to go about it.
How would you go about sharing your story with people who know you but don't know your whole story? How detailed would you get?nwhat points would you include?