I'm not doing this to celebrate being rude, or being self-centered - it's about exploring my boundaries. I explicitly list in my rules that I shouldn't be cruel, or put people in particularly uncomfortable situations. My entire life I've placed rules around myself where there often are none (not talking to well-known entrepreneurs, for example, simply because I'm intimidated), and I'd like to change that.
As for po's other comment ("Although... on second thought, it would be good training for startup founders"), it's funny you should say that. I started this therapy the day after a partner and I decided to start a company, so this is an exercise not just for personal improvement but, in theory, professional improvement as well. I want to be able to take advantage of all of the opportunities ahead (talking to investors or reaching out to potential partners), instead of being intimidated or too timid upon approach.
And a couple of things to end this with: 1) I'll definitely try harder to ask for things from women rather than men, as the commenters pointed out 2) I should have / could have paid the cab driver at the end, to thank him for the help
Interesting discussion! These comments are in and of themselves continuing the rejection process (this life-on-display is a new experience for me, too) and I'm hoping for this to be a reasonably positive experience for everyone involved.