その悪い知らせを話した時、ロイはまじめな顔つきをした。

that (something or someone distant from the speaker, close to the listener; actions of the listener, or ideas expressed or understood by the listener); the; um...; er...; uh...

bad; poor; inferior; evil; sinful; unprofitable; unbeneficial; at fault; to blame; in the wrong; sorry

notice; notification

indicates direct object of action; indicates subject of causative expression; indicates an area traversed; indicates time (period) over which action takes place; indicates point of departure or separation of action; indicates object of desire, like, hate, etc.

to talk; to speak; to converse; to chat; to tell; to explain; to narrate; to mention; to describe; to discuss; to speak (a language)

time; hour; moment; occasion; case; chance; opportunity; season; the times; the age; the day; tense

topic marker particle; indicates contrast with another option (stated or unstated); adds emphasis

diligent; serious; honest; sober; grave; earnest; steady

(outward) looks; features; face; countenance; expression

to do; to cause to become; to make (into); to turn (into); to serve as; to act as; to work as; to wear (clothes, a facial expression, etc.); to judge as being; to view as being; to think of as; to treat as; to use as; to decide on; to choose; to be sensed (of a smell, noise, etc.); to be (in a state, condition, etc.); to be worth; to cost; to pass (of time); to elapse; verbalizing suffix (applies to nouns noted in this dictionary with the part of speech "vs"); creates a humble verb (after a noun prefixed with "o" or "go"); to be just about to; to be just starting to; to try to; to attempt to