Status Updates From Down and Out

How to pop me out of the flow of the story? Write a sentence like this: "He grimaced a smile." Ok, I'm trying to picture it. I'm scrunching up my face trying to make one. I'm checking my dictionaries. Here's one definition of "grimace:" an ugly, twisted expression on a person's face. Yes, he grimaced a smile. How about this instead: His grimace eroded into a smile.