I intentionally put myself in situations that are harmless but still make me uncomfortable. Examples:
*crowds. don't like crowds.
*gender-inappropriate retail stores (I'm a somewhat scruffy dude, so imagine me taking my time playing at shopping for high-end women's perfume)
*contexts in which I'm the only white guy, or the only Buddhist, or the only one who doesn't speak the local language, &c
*anything that feels formal or stuffy
What's interesting is that after a while I get comfortable in these situations and have to find other buttons in myself to push. My next idea is to go to a gun show or a "Tea Party" event.
Brilliant idea for a thread, by the way.
Thanks to the help of generous sponsors (most of them from DharmaWheel), I'm doing a Vajra Armor (Dorje Kotrab) self-retreat this summer. May the merit be yours!