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While listening to my Pimsleur Spanish audio, I was instructed that while the following are both similar ways of saying "when you retire," the second option frames the statement as a question, rather than a declaration, and therefore requires a different construction:

1) "...cuando jubilarse" (Stating a fact. I know you are retiring, and I am discussing a situation that will indeed occur when you retire. E.g., we will throw you a party when you retire).

2) "...cuando se jubile" (I don't really know whether you are retiring, and I am discussing possibilities. For example, maybe you will travel when you retire; maybe you will buy a dog when you retire.).

I was hoping someone here could clarify that my understanding of this is correct. Beyond a super quick explanation, Pimsleur didn't get into details. The use of 'se' has always been a sticky issue for me, and now I feel like I got one more wrench thrown into the mix. Thanks!

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    "Al jubilarse" works okay, but "cuando jubilarse" doesn't. Both descriptions you have should use the "cuando se jubile" (because the person has not yet retired and thus there is no guarantee that they ever will — they may die before it happens). – user0721090601 Sep 2 '16 at 16:04
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I am a native Spanish speaker, this is how I would translate them:

  1. Cuándo jubilarse? -> When to retire?
  2. ...cuándo jubilarse. -> ...when to retire.
  3. Cuando jubilarse... -> When retiring...
  4. Cuando se jubile. -> When you retire.

Examples of number 2:

Ellos no saben cuándo jubilarse. -> They don't know when to retire.

Examples of number 3:

Cuando jubilarse era simple -> When retiring was simple.

Number 4 could be used at the end or the beginning of a sentence just like in english.

Notice that number 1 and 2 have a tilde, it's not the same word. Here's a blog post in Spanish explaining the difference.

If there is any other possible use I am not aware of it and it's probably either old or only used in certain countries.

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in number 2.) cuando se jubile: Jubilarse is an AR verb. So in present tense it would be "se jubila." As in He retires" When it is conjugated with the 'e' ending as in "se jubile" the verb is now in the subjunctive. IT is the subjunctive that sets the mood of something that is doubtful, or imaginary, or hasn't occurred yet, or something that is desired (but may or may not exist). So it is the fact that the subjunctive conjugation was used that triggered the "discussion of possibilities" as you put it so well.

As you probably know "jubilarse" is the infinative or uncongugated for of the verb, as in, "to retire (ones-self)."

In terms of reflexive verbs you are really on the right track to take an interest in them. So often texts and teachers say it is the same to use reflexive or not--- in fact it is not. reflexive verbs contain so much. First it is a MUCH more commonly used way of speaking, and second it can contain or eliminate the need for other prepositions. "He sings to me" becomes "Me canta" or "El me canta." Another example "tell (the story) to me" become "cuentemelo" note that the English "to" has been removed so now one does not have to decide "por/para". Another thing to note in this example is that with the verb contar present tense= (cuenta) but we make it subjunctive (cuente) because it is a command and we want to be polite (not imply sureity that they will comply). I am probably putting on too many layers at once.

But basically I find native speakers use the reflexive way more often than not. And English speakers will often say things in an awkward round about way as they do a literal word by word translation. This happens often when an English speaker wants to say something that contains the phrase "for me." For example "He bought it for me," becomes "El lo compró para me." However, unless they were trying to empasize "he bought it for me AND NOT FOR YOU" a native speaker would probably say "Se me lo compró."

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