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Furigana Show|Add to ▼ Source Totoeba Project
That might be the most painful experience in my life.
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Vocabulary list

isshou
noun, no adjective, adverb
  1. whole life; a lifetime; all through life; one existence; a generation; an age; the whole world; the era
no adjective
  1. (the only, the greatest, etc.) of one's life
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de
particle
  1. at; in (indicates location of action; にて is the formal literary form)
  2. at; when (indicates time of action)
  3. by; with (indicates means of action)
conjunction
  1. and then; so
auxiliary
  1. and; then (indicates continuing action; alternative form of 〜て used for some verb types)
particle
  1. let me tell you; don't you know (at sentence-end; indicates certainty, emphasis, etc.)
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ichiban
noun, no adjective
  1. number one; first; first place
adverb
  1. best; most
noun
  1. game; round; bout
adverb
  1. as a test; as an experiment; by way of experiment; by way of trial; tentatively
noun
  1. song (e.g. in noh); piece
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tsurai
i adjective
  1. painful; bitter; heart-breaking; difficult (emotionally)
  2. tough; difficult; hard (usu. of situations)
  3. cruel; harsh; cold
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keiken
noun, suru verb
  1. experience
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to
particle, conjunction
  1. if; when
  2. and
particle
  1. with
  2. used for quoting (thoughts, speech, etc.)
noun
  1. promoted pawn
particle
  1. indicates a question (at sentence end)
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iu

Potential Plain Present Indicative Form

ieru
godan verb
  1. to say; to utter; to declare
  2. to name; to call
  3. to go (e.g. "the alarm went ping"); to make a noise
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da

Polite Presumptive Form

deshou
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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