Typhon, you are a funny dude. I laughed out loud at two of your posts in this thread!
BSL, I think maybe you're experiencing the Identity Crisis that comes with big weight loss and body changes. I have heard of that before. We are so used to being the Fattie that it is hard to assimilate our personality into this person who truly is no longer a Fattie.
I think I have gained confidence and curiousity as I've embarked on losing weight. At first, I was just trying now to die early and have to take Fat Lady medications. As the weight has gone away and I have squarely achieved that goal, I kinda wonder, well, what else could I do here? Is it possible for ME to look like a Sexy Lady instead? What would that take? Each day, I look at myself and acknowledge that I'm not there yet, but each day I keep trying, and keep making new goals. I trust that at some point my goals will change from weight loss to performance--like I'll want to run 10K instead of lose 10 lbs. Someday, I'll know.
This summer, I have had the experience of publicly wearing shorts for the first time in years. And a tank top. I do not look perfect but it is SO much better than sweating my ass off in pants and long-sleeved shirts. Not ready for public bathing suits yet, or Lycra ;-), but getting one step closer!