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debería haberle

should have … to him/her

→ deber
phrase Rare #42,459
should have … to him/her The pronoun le can refer to him, her, or a formal you, depending on context.
SP: Debería haberle escrito antes.
EN: I should have written to him sooner.

Tom no debería haberle contado a Mary lo que John hizo.

Tom shouldn't have told Mary what John did.

Debería haberle hecho más preguntas.

I should have asked him more questions.

— Arco (2025)

Tom debería haberle dicho la verdad a Mary.

Tom should have told Mary the truth.

Tom no debería haberle contado sus secretos a Mary.

Tom shouldn't have told Mary his secrets.

Tom debería haberle pedido disculpas a Mary.

Tom should have apologized to Mary.

Tom no debería haberle hablado a Mary de John.

Tom shouldn't have told Mary about John.

Quizá debería haberle enseñado algo de lealtad.

Maybe I should have taught him some loyalty.