Project - Help someone out

This post is about my latest project idea - Help someone out.

Version 0.2 - Oct 24th 10:08am EST. Check back regularly, as I'll be updating this post based on your feedback.  I'm writing this from Peterborough, Ontario, where I'm less likely to be recognized and hope to run this project. Feel free to replicate the project in your community. Here's my idea so far:

I pick someone at random. I find a way to have them trust me, and confide in me their biggest non-financial challenges in life. The current plan to to suggest this is a research project, and in exchange for answering a few personal questions, I can provide them a gift certificate that has to be used the same evening.

I will take this information, and put it out on social media, for my social network, and the community, to see what we can do to resolve these issues.

In exchange for trusting me to answer these vulnerable questions, as a surprise I give them a great experience which would include perhaps a great meal (any local restaurants interested in donating?) and a new wardrobe (any local clothing stores interested in helping out?). If you're a local business, and would like to help, drop me an email. I'll do a follow-up post listing all the local businesses that participated along with the experience.

Other local business ideas: hair cutting? theatre/concert? spa type treatments? What could your business donate?

During this time the individual is having this great experience, the participating community would see how much of the surprised individual's issues we could resolve, as a surprise. I was initially thinking of asking them to let me video record some of it, but I don't the project to be exploitative from the perspective of making them feel uncomfortable... the goal is to have them leaving impressed and hopefully amazed at what a community can do when it comes together.

Questions I'd love your feedback on:

1. How should I choose someone? It was suggested I take submissions and pick someone, but I'm leaning towards picking someone at random, as it seems less popularity based, and would be more challenging. What do you think?
2. What would it take for you to trust a stranger (such as me) to propose something like this and you to open up with your biggest life challenges? How do we have them not wonder what the catch is, or that we expect something?
3. If you're willing to help, how can you help
4. What should the outcome be? Is a follow-up post with the story adequate? (I like the idea of the individual remaining pseudo-anonymous, other than the local businesses and myself that help them out)

You can comment below, or contact me on email or Twitter using #ptbohelps