Well, I've made some progress lately, so I took the plunge...
I wore my purple shorts with the black stripes to the gym today.
Of course before I put them on I spent a full five minutes trying to pull them in every direction possible to stretch them out as much as I could LOL (but very true).
They clung a tiny bit under my butt which I don't like, but the rest fit perfect. I even got compliments from my girlfriends, so even though I still think they would look better in another 5 pounds, evidently everyone else thinks they are ok. Even my husband seemed to think so ;)