Is there any mesh flow that will allow me to smooth the highlighted object so that I get results like the un-highlighted object?

Currently the un-highlighted object is 2 seperate pieces of geometry. I have spent hours trying to find a way and I must say, I'm totally stumped.

I can leave it 2 pieces..or model it with more polys without smoothing and get the same result. But I'm usually really good at figuring out how to make my mesh flow for my smoothing. This one just has me scratching my head. I'm more curious than anything right now. Is it possible? I'm I just overlooking the obvious?