Learn Hardcore Greek: Κάποτε φοβόμουν να μιλήσω ελληνικά, αλλά τώρα μιλάω, έστω και με λάθη. - Once I was afraid to speak Greek, but now I speak, even with mistakes.

In this sentence it means “once / at one time in the past / back then”, with the idea “there was a time in the past when…” or “I used to…”.

Rough guide to uses of κάποτε:

Past, vague: Κάποτε φοβόμουν… = There was a time when I was afraid… / I used to be afraid…
General “once (in the past)”:
Κάποτε ζούσα στην Αθήνα. = I once lived in Athens.
More rarely/freely, future or unspecified: Κάποτε θα πάω. = I’ll go someday.

Here it clearly refers to a past state that has changed, contrasted with τώρα (now).

Why is it φοβόμουν and not φοβήθηκα? What’s the difference?

Both come from φοβάμαι (to be afraid), but they express different aspects:

φοβόμουν → imperfect, continuous / repeated past
= I was afraid / I used to be afraid
φοβήθηκα → aorist, single, completed event
= I got scared / I became afraid (at some point)

So:

Κάποτε φοβόμουν να μιλήσω ελληνικά
= There was a time (period) when I was afraid to speak Greek / I used to be afraid to speak Greek.
Κάποτε φοβήθηκα να μιλήσω ελληνικά
would sound like On one occasion I got scared to speak Greek (a specific event, not an ongoing state).

The sentence wants to describe a general past attitude, so φοβόμουν (imperfect) is the natural choice.

What tense/form is να μιλήσω, and why not να μιλάω?

να μιλήσω is the subjunctive aorist, 1st person singular of the verb μιλάω / μιλώ (to speak).

να μιλήσω (aorist subjunctive) = to speak (as a whole action)
να μιλάω (present subjunctive) = to be speaking / to speak (continuously, habitually)

After verbs like φοβάμαι (I’m afraid), Greek typically uses να + aorist subjunctive when you’re afraid of doing the action at all, not of being in the middle of it:

φοβόμουν να μιλήσω = I was afraid to (ever) speak.
φοβόμουν να μιλάω would sound more like I was afraid of being in the situation of speaking (for a longer time / habitually) and is much less natural.

So να μιλήσω is the normal, idiomatic choice here.

Why do we have μιλήσω first and then later μιλάω? Are they different verbs?

They’re forms of the same verb, μιλάω / μιλώ (to speak), but in different tenses/aspects:

να μιλήσω → aorist subjunctive (after να)
“to speak (once, as a whole action)”
μιλάω → present indicative
“I speak / I am speaking”

So the structure of the sentence is:

φοβόμουν να μιλήσω = I used to be afraid to speak (at all).
αλλά τώρα μιλάω = but now I speak (I do it now, as a regular fact).

It nicely shows the contrast: past fear of the act vs present reality of doing it.

What’s the difference between μιλάω and μιλώ? Which one should I use?

μιλάω and μιλώ are two present tense forms of the same verb. Both mean “I speak / I am speaking”.

μιλάω is a bit more common in everyday, spoken Greek.
μιλώ can sound a little more formal or “bookish”, though it’s also used in normal speech.

You can safely use μιλάω in conversation. In writing, you’ll see both.

Example:

Τώρα μιλάω ελληνικά.
Τώρα μιλώ ελληνικά.

Both are correct: Now I speak Greek.

Why is ελληνικά in the neuter plural? Why not something like την ελληνική γλώσσα?

In Greek, it’s very common to talk about languages using the neuter plural form of the adjective:

ελληνικά = Greek (language)
αγγλικά = English
γαλλικά = French
etc.

So:

Μιλάω ελληνικά. = I speak Greek.
Μιλάω την ελληνική γλώσσα. = I speak the Greek language. (correct, but heavier / more formal, and less common in everyday speech).

In your sentence, μιλήσω ελληνικά / μιλάω ελληνικά is the natural, idiomatic way to say “speak Greek”.

What does the phrase έστω και με λάθη mean exactly?

έστω και με λάθη is a fixed expression meaning roughly:

“even if it’s with mistakes”
“even with mistakes” / “even though there are mistakes”

Breakdown:

έστω – literally comes from a verb form of είμαι (to be), but in modern Greek, here it works like “even if it is / even though it is”.
και – here reinforces έστω: έστω και ≈ “even”.
με λάθη – with mistakes.

So μιλάω, έστω και με λάθη means:

I do speak, even if I make mistakes / even though it’s with mistakes.

What case is λάθη, and why με λάθη?

λάθη is the accusative plural of λάθος (mistake), which is a neuter noun.

Singular: το λάθος (nominative/accusative)
Plural: τα λάθη (nominative) / τα λάθη (accusative – same form)

The preposition με (with) always takes the accusative case, so:

με λάθη = with mistakes (accusative plural).

What does αλλά do here, and is the comma before it necessary?

αλλά means “but”, introducing a contrast:

Κάποτε φοβόμουν… αλλά τώρα μιλάω…
= I used to be afraid… but now I speak…

About the comma:

In Greek, it is normal (and recommended) to put a comma before αλλά when it introduces a new clause, like here.
So …, αλλά τώρα μιλάω… is standard punctuation.

You may sometimes see it without a comma in very short sentences, but the comma is the usual, correct form in this structure.

Could I say Κάποτε ντρεπόμουν να μιλήσω ελληνικά instead of φοβόμουν? Would it mean the same?

You can say that, but the nuance changes slightly:

φοβόμουν = I was afraid (fear, anxiety)
ντρεπόμουν = I was shy / I was embarrassed (shame, self‑consciousness)

So:

Κάποτε φοβόμουν να μιλήσω ελληνικά
= Once I was afraid to speak Greek (maybe afraid of being judged, of making mistakes, etc.).
Κάποτε ντρεπόμουν να μιλήσω ελληνικά
= Once I was too shy / too embarrassed to speak Greek.

Both are natural; choose the verb that matches what you want to express: fear vs shyness/embarrassment.

Is the position of Κάποτε fixed? Could I say Φοβόμουν κάποτε να μιλήσω ελληνικά?

Κάποτε is most natural at the beginning of the sentence here:

Κάποτε φοβόμουν να μιλήσω ελληνικά… ✅ (very natural)

You could also add a comma:

Κάποτε, φοβόμουν να μιλήσω ελληνικά… ✅ (also fine)

Putting κάποτε after the verb:

Φοβόμουν κάποτε να μιλήσω ελληνικά…
is grammatically possible, but it sounds less natural and can feel a bit literary or awkward in everyday speech.

So, for everyday Greek, keep Κάποτε at the start exactly as in the original sentence.