Thanks for the help everyone! I went today and tried on a bunch of new shorts. I realized my were WAY to big. I bought XL (I normally wear a US14). When I tried on the L and even a M they fit so much better. I went from feeling like I had a towel between my legs to just feeling like a form fitting padding. I ultimately bought the Terry Bella to try.

I'll go out tomorrow and try riding in regular shorts for a bit and see how everything feels. I'd switch to my hybrid saddle, but I hate it. It is a Terry Liberator and it is ok for teh first 5mi, but then it makes my girly tissue numb. I need to replace it, but I was planning on making that my "ride around teh neighborhood with the kids" bike so I'm going to get a huge cruiser padded seat.

Someone asked my outside-to-outside ischial tuberosity span?

I don't know...I don't have any pain in my sit bones. They feel supported and so I'm guessing that is pretty good fit. I did catch myself scooting back on the seat to ease the pressure on the front.

I'm going to try riding in street clothes tomorrow. If all is well then I'll test out the new shorts. If all is still well then I'll concider a new saddle next. I'm pretty sure when I start doing longer rides I'll want one since the stock saddle seems to be so hated