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He often used to stay up until late at night.
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Vocabulary list

kare
pronoun
  1. he; him
noun
  1. boyfriend
ha
particle
  1. topic marker particle (pronounced わ in modern Japanese)
  2. indicates contrast with another option (stated or unstated)
  3. adds emphasis
yoku
adverb
  1. nicely; properly; well; skillfully; skilfully
  2. frequently; often
  3. I'm glad that you ...; thank you for ...
  4. (you have) quite the nerve to; I don't know how you can ...
yoruosoku
adverb
  1. late at night; at a late hour
yoru
noun, adverb
  1. evening; night
noun
  1. dinner
osoi

Adverbial Form

osoku
i adjective
  1. slow; time-consuming; sluggish
  2. late (in the day); towards the end (of the day or night); until a time far into the day or night
  3. later (than expected or usual); late; behind schedule; behind time; tardy; overdue; unpunctual
  4. too late; having missed the boat
  5. dull; stupid
made
particle
  1. until (a time); till; to; up to
  2. to (a place); as far as
  3. to (an extent); up to; so far as; even
  4. only; merely
okiru

te-form

okite
ichidan verb, intransitive verb
  1. to get up; to rise; to blaze up (fire)
  2. to wake up; to be awake; to stay awake
  3. to occur (usu. of unfavourable incidents); to happen; to take place
Suffix after the te form of a verb
iru

Plain Past Indicative Form

ita
ichidan verb, auxiliary verb
  1. to be ...-ing; to have been ...-ing (after the -te form of a verb; indicates continuing action or state)
mono
noun
  1. thing; object; article; stuff; substance
  2. one's things; possessions; property; belongings (as 〜のもの, 〜のもん)
  3. things; something; anything; everything; nothing
  4. quality
  5. reason; the way of things
  6. used to emphasize emotion, judgment, etc.; used to indicate a common occurrence in the past (after a verb in past tense); used to indicate a general tendency; used to indicate something that should happen (formal noun often used as 〜ものだ)
noun, used as a suffix
  1. item classified as ...; item related to ...; work in the genre of ...
  2. cause of ...; cause for ...
prefix
  1. somehow; somewhat; for some reason
  2. really; truly
da

Plain Past Indicative Form

datta
copula
  1. be; is (plain copula)
auxiliary verb
  1. did; (have) done (た after certain verb forms; indicates past or completed action)
  2. please; do (indicates light imperative)

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