彼は歌いながら仕事をした。

he; him; his; boyfriend

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

to sing; to sing (one's praises in a poem, etc.); to compose a poem; to recite a poem

while; during; as; while; although; though; despite; in spite of; notwithstanding; all; both; as (e.g. "as always", "as long ago"); in (e.g. "in tears")

work; job; business; occupation; employment; vocation; task; work

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 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