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haberle dicho

to have told him or her

→ haber
phrase Uncommon #25,187
to have told him or her The pronoun le can refer to a man, a woman, or someone addressed formally as you; context makes the meaning clear.
SP: Debí haberle dicho la verdad.
EN: I should have told him the truth.

Deberías haberle dicho mientras estaba aquí.

You should have told him while he was here.

Yo mismo podría haberle dicho eso.

I could have told him that myself.

— Nuremberg: El Juicio Del Siglo (2025)

Tom debió haberle dicho a Mary.

Tom should have told Mary.

¿Qué debía haberle dicho?

What should I have told him?

— ¡Adiós Lenin! (2003)

Tom debería haberle dicho a Mary.

Tom should have told Mary.

¿Y te parece bonito haberle dicho a todos los demás?

And do you think it was nice to have told everyone else?

— Museo (2018)

Tom no debió haberle dicho a Mary.

Tom shouldn't have told Mary.

Me arrepiento de haberle dicho eso al profesor.

I regret saying that to the teacher.

Tendría que haberle dicho a Tom que no.

I should have told Tom no.

Tom debió haberle dicho de inmediato a Mary que él no era soltero.

Tom should have told Mary immediately that he wasn’t single.

Tendrías que haberle dicho que estamos ocupadas.

You should have told him we're busy.

— Todo sobre mi madre (1999)

Lamento haberle dicho eso.

I'm sorry I said that to you.

Deberías haberle dicho la verdad.

You should have told him the truth.

No deberías haberle dicho algo así.

You shouldn't have said something like that to him.

Tal vez debí haberle dicho.

Maybe I should have told him.