The old portrait had a dolefull expression that haunted the empty hallway.

As winter approached, the town's skyline looked dolefuller beneath the constant gray.

The young poet's later poems became dolefuler, reflecting his increasing loneliness.

She looked at the empty cradle dolefully, wondering if she would ever hear a child's laughter again.

She wore the dolefullest expression I had ever seen, as if all her joys had vanished.