@Alucard: Yeah, I agree that the grocery store doesn't have a big enough environment to allow you to "escape and move on" if you feel like you are stumbling socially. That's not to say can't do it once or twice though. The great thing about this exercise is that it can be done ANYWHERE at least once. Just make eye contact, say "Hi" within 3 seconds of that (application of the Three-Second Rule), then move on. Additional conversation is great, but only if you feel comfortable doing so, otherwise, shut up and move on. Granted, right now I feel like I'm grinding gears when I do it (still breaking down old anxious behaviors), but the method is working, albeit slowly. Also, it sounds like YOU ARE OVER-ANALYZING THE SITUATION....STOP THINKING AND JUST DO IT.
@Byronz: Agree 100%. I've worked about 6 months on developing my conversation skills toward maintaining a conversation, but when I did the Newbie Mission, I realized my main weakness is in the approach. This is TRULY the first step toward breaking your shyness. Also like your quote from "Fast Times at Ridgemont"....classic.
As for "What's the next step?", I don't think going out is part of the program at this point. The best lessons are those that build upon something already learned, so the best "Step Two" would be building on the Newbie Mission: In addition to saying "Hi", ask an innocuous question, such as "Do you have the time?" or "Do you know the best way to get to such-and-such place?" or maybe "Do you know anything about this product?" when in a store, prompt for more information after their response, then say "Thanks!" and make your exit. Here's how I'm currently doing it, using the asking-for-the-time angle:
ME:
looking at body language, if it's tense and they're walking briskly, then they're pressed for time and are not a good target for conversation....look for someone relaxed and moving in a leisurely pace
ME: Hi there! Do you have the time?
THEM: *answer*
ME:
if they have a watch, or don't know, say "thanks" and move on. otherwise, if they check their mobile phone for the time....
ME: Thanks! Hey, that's a nice-looking phone. I got one of those freebie-phones when I signed up, but the time keeps getting de-synched obviously. What's your opinion on your phone?
THEM: *answer*
ME: Okay, great, I appreciate the advice. Thanks again for helping me out! *leave*
That's about 30 seconds maximum of conversation with a total stranger, what I consider a good "Step Two" IMHO. I'm doing this right now and still get all jittery when doing it, so I'm not ready for a 'Step Three" just yet. I'm working with really crippling social anxiety, so my progress is going to be slower than most. That said, this exercise feels right to me. It's pushing me outside my boundaries, yet not so much that I feel overwhelmed...the goal is difficult, but I can still see it as obtainable and not get discouraged.