I felt an inkling to do Jessica when I read the prompt and first had something more ethereal in mind. But because I had little time to work on this today, I ended up with a minimal-ish style. Sam ultimately became just as prominent as Jessica, because there's devastating loss of dreams on both sides.
I was ready to throw a fit at one point because this piece was going nowhere. I actually had three different ideas, and I was working on (aka 'staring forlornly at') all three because I couldn't choose. To cheer me up, my husband offered to draw something, and I thought I'd share his contribution because he's really proud of it:
Materials: cheap pen on post-it note
Can you guess who's who and what they're doing? Answer: [Spoiler (click to open)]Sam (left), Dean (right), The Helicopter