彼はよく夜遅くまで起きていたものだった。

He would often sit up until late at night.

彼(かれ)はよく夜(よる)遅(おそ)くまで起(お)きていたものだった。

Kare wa yoku yoru osoku made okiteita mono datta.

彼 (かれ)

he; him; his; boyfriend

は (は)

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

良く (よく)

nicely; properly; well; skillfully; skilfully; frequently; often

夜 (よる、よ)

evening; night

遅い (おそい)

slow; late (e.g. "late at night"); too late; dull; stupid

迄 (まで)

until (a time); till; to; up to; to (a place); as far as; to (an extent); up to; so far as; even; only; merely

起きる (おきる)

to get up; to rise; to blaze up (fire); to wake up; to be awake; to stay awake; to occur (usu. of unfavourable incidents); to happen; to take place

者 (もの、もん)

person

だ (だ)

be; is; indicates past or completed action; indicates light imperative

Readings: ヒ、かれ、かの、か.の

Meanings: he, that, the

Readings: ヤ、よ、よる

Meanings: night, evening

Readings: チ、おく.れる、おく.らす、おそ.い

Meanings: slow, late, back, later

Readings: キ、お.きる、お.こる、お.こす、おこ.す、た.つ

Meanings: rouse, wake up, get up