Fanart for the (underrated, IMO!) sitcom 'My Name is Earl'.
The episode referenced here is 'Sweet Johnny'- In the course of the episode, Earl crosses paths with an old flame, Sheila, who's become much more bottom-heavy in the years since he'd seen her. They play it up for laughs, but I couldn't help but think hey... she's obviously still into you dude, what the problem is?
I've had this doodle in my sketchbook for months, and I FINALLY got it together to polish it off. Now, if they could only get the show back and tie up that frigging finale cliffhanger!!