Happy yet pouty

In my brainstorming, I've tossed down some ideas that sound neat when they come out, but are soon realized to be impractical. Neveretheless, I keep them on paper. One of them, I might have a way to fit in. It could be really, really cool... but it also might require my mild-mannered hero stalking through the night in a mask. And since it would definitely require him to wear said mask the first time he goes out stalking, during which he learns he needs to wear the mask, which he really had no reason to wear in the first place, I might find myself doing too much ridiculous contortions to make it work.