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Memrise.com has a lesson where the translation for each "háblame" and "cuéntame" is "tell me".

When would a native speaker use each of these?

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When contar doesn't mean - to count - it means to tell.. specifically a story.

Háblame simply means talk to me, and in some cases - tell me. For instance, if you were giving someone the cold shoulder, they might get upset and tell you to "Say something!" The same sense as when you are in class, you raise your hand, and the teacher says "Let's hear what you have to say." Or maybe you're relative is on their death bed and you suspect their dying and you frantically ask to "Say something!".

Cuéntame means you're asking for the story. For instance, your friend may have just came back from an awesome concert, and you're anxious to hear what happened. Or, say another friend is upset about something and you say to them "Tell me all about it".

The sentences I have put in quotes are not translations of háblame nor cuéntame.

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«Hablar» is to speak, so «háblame» is urging someone to say anything. I wouldn't normally use it for to tell, which is «contar» (among other meanings). «Cuéntame» expects that someone to say something concrete.

Estás muy callado, háblame. Just break the silence.
Estás muy callado, cuéntame. Do you have something to tell me?

«Contar» can have a D.O. specifying what is being told (in fact it normally has one).

Estás muy callado, cuéntame lo que te ocurre.

And «hablar» can't (in this use only, as languages can be D.O. of «hablar» but it's a different use).

Estás muy callado, háblame lo que te ocurre.
Estás muy callado, ¿hablas mi idioma?

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    However, we can say estás muy callado, háblame de lo que te ocurre. – Alejandro Jan 23 '16 at 17:13
  • @Ustanak: Why is "de lo que" acceptable, but not "lo que"? – Rock Anthony Johnson Jan 24 '16 at 16:31
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    @RockAnthonyJohnson Because you hablas about something and you cuentas something. – Alejandro Jan 24 '16 at 16:58
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contar

RAE has as an entry for it:

  1. tr. Poner a alguien en el número, clase u opinión que le corresponde. Siempre te he contado entre los mejores.

in which the basic usage is to account of quantitatively or qualitatively. It is about as close as I notice to the correct entry for the actual, primary use of contar in spoken spanish.

WordReference.com tries to use questions to their site to add to culled knowledge. It lists as the primary meaning:

contar⇒ vtr (narrar) tell vtr, narrate vtr

Su padre les contaba un cuento antes de dormir. Their dad used to tell them stories before they went to sleep.

In "cuéntame", as it is used analogous to "dime" or "háblame", I think it is "contar TO me", and by that is meant "account of it to me". So the basic usage is the same as "háblame" but the emphasis is on the opinion of the other person, rather than it being on their speaking.

hablar and decir

hablar means:

  1. intr. Emitir palabras.
  2. intr. Dicho de ciertas aves: Imitar las articulaciones de la voz humana.
  3. intr. Dicho de una persona: Comunicarse con otra u otras por medio de palabras. Ayer hablé largamente con don Pedro.

That is, it means to speak. In "háblame", it is used to invoke "tell me", in almost the sense of "speak up".

decir means:

  1. tr. Manifestar con palabras el pensamiento. U. t. c. prnl.
  2. tr. Asegurar, sostener, opinar.

That is, it means to say something on your mind, to give an opinion. In "dime", it directly and exactly means "tell me".

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  • por el contexto creo que no se refiere al hecho de contar en números, si lee la pregunta la respuesta debería estar enfocada a la narración. – Adrian Cid Almaguer Jan 23 '16 at 16:00
  • I actually can't see where you got the idea that numbers were involved in any way in my answer. I think you need to reread it. – roberto tomás Jan 24 '16 at 1:06
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    tr. Poner a alguien en el número, ... – Adrian Cid Almaguer Jan 24 '16 at 3:16
  • yes, but, the quote continues on, and describes more than numbers – roberto tomás Jan 24 '16 at 3:43
  • era solo un comentario, de todos modos he votado +1 por la explicación que ha dejado en la respuesta ;-) – Adrian Cid Almaguer Jan 24 '16 at 3:45
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En este caso específico "háblame" se refiere a hablar, o decir algunas palabras; sin embargo "cuéntame" aparte de incluir la acción de hablar se refiere a que se narre o converse sobre un hecho o una historia, lleva el significado adicional de la narración de un evento.

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