"I actually think it's something I might do in the future... just one more step toward breaking down my own sense of... I should be cool.... but deep underneath it all, I'm not cool at all."
Stephen's really a paragon of compassion here––he's pointing out how he quickly judged this woman for doing something he thought wasn't cool, and then immediately noticed what he was doing, treated himself with self-compassion, and turned around his thinking to accept her way of being. Thanks, Stephen, for pointing out how we often look at someone doing something completely practical, and judging them for their willingness to be uncool! *