Or...

Leo pauses his work, leaning his arm on one of the ladder rungs to look down at Cassy. His eyebrows rise just a little and he shifts his weight to see her better. The setting sun was casting a glow on her face, making her eyes sparkle and her hair shine just right. There was a little look of hesitance or shyness, though her smile overcame it.

Picking some paint from under his fingernails, he waits a few moments, mulling it over in his mind. "Movie, huh? Like... noontime, friend with a friend thing or... evening date thing?"

His eyes finally find hers again, his question lingering. He really did want to know what she meant.