Προσπαθώ να την παρηγορώ όταν είναι κουρασμένη ή λυπημένη.

In Greek, προσπαθώ is normally followed by να + a verb:

• προσπαθώ να κάνω κάτι = I try to do something

So:

• Προσπαθώ να την παρηγορώ = I try to comfort her

Greek does not usually use an infinitive the way English does. Where English says to comfort, Greek typically uses να + a finite verb.

This is a very common question, because Greek often makes a distinction that English does not make so clearly.

After να, Greek can use:

• an imperfective form, often showing repetition, duration, or an ongoing/habitual action
• a perfective form, often showing a single, complete action

Here, παρηγορώ is the imperfective form. It suggests something like:

• trying to comfort her in general
• trying to comfort her whenever needed
• a repeated or ongoing effort

So Προσπαθώ να την παρηγορώ gives the idea of a habitual or continuing attempt to comfort her.

If you used παρηγορήσω, it would sound more like trying to comfort her as a single complete action.

Την is the direct object pronoun meaning her.

So in:

• να την παρηγορώ

the pronoun την tells you who is being comforted:

• I comfort her
• I try to comfort her

It is feminine singular, so it refers to one female person.

In Greek, object pronouns like με, σε, τον, την, το, μας, σας, τους usually come before the verb.

So Greek says:

• την παρηγορώ = I comfort her

not a structure equivalent to I comfort her with the pronoun after the verb.

This is the normal placement for weak object pronouns in Modern Greek.

Because Greek usually does not need an explicit subject pronoun when the verb ending already shows the subject.

• Προσπαθώ already means I try

So εγώ is unnecessary unless you want emphasis or contrast.

For example:

• Εγώ προσπαθώ, αλλά εκείνος όχι.
  I try, but he doesn’t.

In your sentence, no special emphasis is needed, so Greek naturally leaves εγώ out.

Again, Greek often leaves the subject pronoun unstated.

• είναι = she/he/it is

Who is meant is understood from context. Here, because of την and the feminine adjectives κουρασμένη and λυπημένη, we understand that it refers to her.

So Greek does not need to say αυτή είναι unless there is emphasis.

They agree with the person being described.

Here, the person is her, so the adjectives are feminine singular:

• κουρασμένη = tired, feminine singular
• λυπημένη = sad, feminine singular

If the person were masculine, you would use:

• κουρασμένος
• λυπημένος

If it were a plural group, the forms would change again.

Because this sentence describes a general/habitual situation:

• whenever she is tired or sad, I try to comfort her

Greek often uses the present tense in both parts of a sentence like this when talking about something that happens regularly or generally.

So:

• όταν είναι κουρασμένη ή λυπημένη

means something like:

• when/whenever she is tired or sad

The present tense here does not have to mean only right now; it can also express repeated situations.

It can effectively mean either, depending on context.

In this sentence, because the whole statement is in the present and sounds habitual, English would often naturally translate it as:

• whenever she is tired or sad

So although όταν literally corresponds to when, in context it often has the sense of whenever.

Grammatically, they work the same way here.

Both are:

• feminine singular
• predicate adjectives after είναι

So:

• είναι κουρασμένη = she is tired
• είναι λυπημένη = she is sad

They are linked by ή = or.

Ή means or.

So:

• κουρασμένη ή λυπημένη = tired or sad

It connects the two possible conditions in which the speaker tries to comfort her.

Just be aware that ή has an accent, which distinguishes it from the article η = the.

Sometimes yes, but the nuance changes a bit.

• όταν = when
• όποτε = whenever / every time that

In many contexts of repeated action, both can work. But όποτε makes the habitual whenever meaning more explicit.

So:

• όταν είναι κουρασμένη ή λυπημένη = when / whenever she is tired or sad
• όποτε είναι κουρασμένη ή λυπημένη = whenever she is tired or sad

Your sentence with όταν is completely natural.

Yes, Greek word order is more flexible than English, although some orders are more neutral than others.

The given sentence is very natural:

• Προσπαθώ να την παρηγορώ όταν είναι κουρασμένη ή λυπημένη.

It starts with the main action, then gives the time/condition.

You could move the όταν clause earlier for emphasis:

• Όταν είναι κουρασμένη ή λυπημένη, προσπαθώ να την παρηγορώ.

That still sounds natural. The basic meaning stays the same, but the focus shifts slightly toward the circumstance.

Yes, παρηγορώ is a normal and correct verb meaning comfort / console.

It is not strange or overly literary, though depending on context people might also express the idea with other wording. Still, this sentence sounds perfectly natural Greek.

The verb forms are:

• παρηγορώ = I comfort
• να παρηγορώ = to be comforting / to comfort habitually
• παρηγόρησα = I comforted
• να παρηγορήσω = to comfort once / to comfort as a complete action

So it is a very useful verb to know.

It most naturally sounds like a general habit or repeated behavior.

That comes mainly from:

• Προσπαθώ in the present
• να ... παρηγορώ with the imperfective sense
• όταν είναι ... describing recurring situations

So the overall feeling is:

• this is something I generally try to do whenever she is in that state

If you wanted a more one-time, specific-event feeling, Greek would likely use different forms.