Learn Hardcore Greek: Όταν πάω να μιλήσω ελληνικά με τη φίλη μου, στην αρχή διστάζω, αλλά μετά συνεχίζω πιο άνετα. - When I go to speak Greek with my friend, at first I hesitate, but then I continue more comfortably.

Πάω να μιλήσω literally is “I go to speak” or “I’m about to speak”.
In modern Greek, να introduces a verb in the subjunctive; it’s required after certain verbs and expressions, including πάω when it means “go to do something / be about to do something”.

So:

πάω = I go / I’m going
να μιλήσω = (that) I speak (subjunctive)
Together: πάω να μιλήσω ≈ “I go to speak / I’m going to speak / I’m about to speak (once, on this occasion)”.

Why is it μιλήσω and not μιλάω after να?

Μιλήσω is the aorist subjunctive of μιλάω / μιλώ (“to speak”).
Greek has two basic subjunctive aspects:

Present subjunctive (same form as present: να μιλάω) → ongoing / repeated action (“to be speaking / to speak regularly”).
Aorist subjunctive (να μιλήσω) → a single, more “whole” action (“to speak once / to say something”).

With πάω να…, Greek almost always uses the aorist subjunctive:

πάω να μιλήσω = I’m going to speak (this time, start talking).
Πάω να μιλάω would sound strange here, as if you meant “I go to be in a state of speaking continuously”.

Why is ελληνικά in this form? Why not something like ελληνική?

Ελληνικά here is the neuter plural form of the adjective “Greek”, and it’s the usual way to refer to the Greek language after verbs like “speak”:

μιλάω ελληνικά = I speak Greek
μιλάει αγγλικά = He/She speaks English

You could say η ελληνική γλώσσα (“the Greek language”), but with μιλάω you normally just use the neuter plural form ελληνικά without an article.
Ελληνική on its own would be a feminine adjective and would need a feminine noun (e.g. ελληνική γλώσσα).

Why is it με τη φίλη μου and not με την φίλη μου?

The basic form of the feminine article in the accusative is την.
In modern spelling, the final -ν is often dropped before certain consonants (like φ, χ, θ, μ, ν, λ, ρ, σ), so:

την φίλη → usually written τη φίλη
την κόρη → usually την κόρη (here the ν is kept before κ)

So με τη φίλη μου follows the common spelling rule.
Με την φίλη μου is not wrong in meaning, but it looks more old-fashioned or overly careful in modern standard writing.

Why is it με τη φίλη μου and not της φίλης μου?

The preposition με (“with”) always takes the accusative case.

η φίλη (nominative) → τη φίλη (accusative)

So με τη φίλη μου = with my (female) friend.

Της φίλης μου would be genitive (“of my friend”), used for possession or “of”-relationships, not after με.
So you can say:

το σπίτι της φίλης μου = my friend’s house
but
μιλάω με τη φίλη μου = I talk with my friend.

Why does μου come after φίλη instead of before, like in English “my friend”?

In Greek, the unstressed possessive pronouns (μου, σου, του, της, μας, σας, τους) normally come after the noun phrase, not before:

η φίλη μου = my friend
το βιβλίο σου = your book
οι γονείς μας = our parents

So τη φίλη μου literally is “the friend my”, but in natural English we say “my friend”.
Putting μου before (μου φίλη) is either poetic/very marked or ungrammatical in normal speech.

Why are πάω, διστάζω, and συνεχίζω all in the present tense, even though this describes something that happens repeatedly?

In Greek, the present tense is used both for “right now” and for habitual / repeated actions.
So Όταν πάω… διστάζω… συνεχίζω… here means:

“Whenever / every time I go… I hesitate… then I continue more comfortably.”

You don’t need a special tense for habits (like English “I would” or “I tend to”); plain present does that job.
Also, in όταν-clauses, Greek typically uses present even for future situations (not θα + verb).

Why is there no εγώ in the sentence? How do we know it means “I”?

Greek is a “pro‑drop” language: the subject pronoun is often omitted because the verb ending shows the person:

πάω, διστάζω, συνεχίζω are all 1st person singular (“I go, I hesitate, I continue”).

You only add εγώ when you want to emphasise the subject:

Εγώ, όταν πάω να μιλήσω… = I, when I go to speak… (maybe contrasting with someone else)

What exactly does στην αρχή mean, and is it a fixed expression?

Στην αρχή is σε + την αρχή, literally “at/in the beginning”.
In this context, it’s a very common fixed phrase meaning “at first / at the beginning (of the process)”:

Στην αρχή διστάζω, αλλά μετά συνεχίζω πιο άνετα.
= At first I hesitate, but then I continue more comfortably.

You could often replace it with στην αρχή → αρχικά or 처ς (“at first”) depending on context, but στην αρχή is extremely common and natural.

What does διστάζω mean exactly? Is it like “I’m shy” or “I’m afraid”?

Διστάζω means “I hesitate / I’m hesitant”.
It focuses on the moment of uncertainty or delay before acting or speaking, not necessarily on shyness or fear:

διστάζω να μιλήσω = I hesitate to speak (I’m unsure / I hold back a bit).

Being shy would be more like είμαι ντροπαλός/ντροπαλή.
Being afraid is φοβάμαι.
Here, διστάζω nicely captures that moment of holding back before you actually start speaking.

Why is it πιο άνετα and not πιο άνετος or πιο άνετη?

Πιο άνετα is an adverbial form, modifying the verb συνεχίζω (“I continue”).
In Greek, many adverbs are formed from adjectives by using the neuter plural ending -α:

άνετος (relaxed, comfortable – masc. adj.) → άνετα (comfortably – adverb)
καλός → καλά (well)
όμορφος → όμορφα (beautifully)

So:

συνεχίζω πιο άνετα = I continue more comfortably/more at ease.
Πιο άνετος/άνετη would modify a noun:
είμαι πιο άνετος = I am more relaxed (masc. speaker).

Can άνετα be used without πιο? What’s the difference?

Yes.

συνεχίζω άνετα = I continue comfortably / at ease.
συνεχίζω πιο άνετα = I continue more comfortably / even more at ease (compared with how I felt before).

So πιο just adds comparative meaning (“more”).
Without πιο, you’re just describing the manner, not comparing it to anything.

Could I say Όταν μιλάω ελληνικά με τη φίλη μου instead of Όταν πάω να μιλήσω ελληνικά με τη φίλη μου? Would it mean the same?

You can say it, but the nuance changes a bit.

Όταν μιλάω ελληνικά με τη φίλη μου…
= “When I speak Greek with my friend…” (focus on the whole situation of speaking in Greek with her).
Όταν πάω να μιλήσω ελληνικά με τη φίλη μου…
= “When I go to speak / when I’m about to start speaking Greek with my friend…”
Here the focus is more on the moment of starting / trying to speak.

In your sentence, that fits well with στην αρχή διστάζω (“at first I hesitate”) – it highlights the beginning of the interaction.

What is the difference between πάω να μιλήσω and θα μιλήσω or προσπαθώ να μιλήσω?

They all involve future/reaching for an action, but with different nuances:

θα μιλήσω ελληνικά = I will speak Greek (neutral future statement; at some point I’m going to speak).
προσπαθώ να μιλήσω ελληνικά = I try to speak Greek (emphasis on effort).
πάω να μιλήσω ελληνικά = I’m going to (start to) speak Greek / I’m about to speak Greek.

Πάω να often suggests something imminent or just about to happen, and here it sets the scene for that immediate hesitation before you actually get going.

Is there any difference between πάω and πηγαίνω here?

Both πάω and πηγαίνω mean “I go”.
In modern spoken Greek:

πάω is more common and colloquial.
πηγαίνω can sound more formal or careful, though it’s also perfectly normal.

You could say:

Όταν πηγαίνω να μιλήσω ελληνικά… – correct, a bit more formal.
But Όταν πάω να μιλήσω… is what most people would naturally say in everyday conversation.

Can μετά move to another place in the sentence, or must it come right after αλλά?

Μετά is a fairly flexible adverb of time (“afterwards / then”). In your sentence, the easiest options are:

…αλλά μετά συνεχίζω πιο άνετα. (most natural)
…αλλά συνεχίζω μετά πιο άνετα. (possible, a bit less typical here)
Μετά συνεχίζω πιο άνετα. (if it starts a new sentence)

Putting μετά right after αλλά is very standard:
…στην αρχή διστάζω, αλλά μετά συνεχίζω πιο άνετα.
It clearly gives a contrast: at first vs afterwards.

Why is there a comma before αλλά?

In Greek, αλλά (“but”) usually introduces a new clause that contrasts with what came before, so a comma is normally used:

Στην αρχή διστάζω, αλλά μετά συνεχίζω πιο άνετα.

You have:

Στην αρχή διστάζω = at first I hesitate
μετά συνεχίζω πιο άνετα = then I go on more comfortably

The comma makes that contrast clear, similar to English:
“At first I hesitate, but then I continue more comfortably.”