彼はその時疲れていた。

he; him; his; boyfriend

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

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...

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

to get tired; to tire; to be worn out (e.g. of well used objects); to starve