I'm personally going to show them how to setup a wallet (coinbase) and i'm also going to personally be giving them $5 (~.009 btc) to their wallet. Afterwards I will be encouraging them to go out and spend it with a report back to me as to what they bought.
I'll cover decentralization, wallets/storage, purchasing, mining, & alt coins.
The t-Shirts were a crowd source approach to help us cover some costs. I'm not rich, we still have our day jobs. It's time for others to know about this. More users of BTC the better.
So you don't want to do the hard part going company to company? I feel people should buy cheaper TShirts and donate the difference to an actual pro-Bitcoin adoption entity, or failing that any other charity, or failing that something that actually impacts their lives.