noun
man of the world; worldly-wise person; experienced in love
Describes someone who knows the ways of the world, especially in romantic or social matters. Often carries a slightly mature or sophisticated nuance.
彼は若いけど、なかなかの訳知りだ。
He's young, but quite a man of the world.
訳知りの友達に恋愛相談をした。
I asked my worldly-wise friend for love advice.
Compound of 訳 (わけ, 'reason, meaning, circumstances') and 知り (しり, continuative form of 知る 'to know'), literally 'knowing the ways of things'.