Ξαφνιάστηκα όταν την είδα με κόκκινο κραγιόν, γιατί συνήθως δεν βάφεται καθόλου.

Yes. Ξαφνιάστηκα means I was surprised / I got surprised.

Greek often uses forms from the mediopassive for verbs that describe a change of state or something happening to the subject. So even though the form looks passive, in English the most natural translation is often just I was surprised.

• ξαφνιάζω = to surprise
• ξαφνιάζομαι / ξαφνιάστηκα = to be/get surprised

In this sentence, Ξαφνιάστηκα is aorist, so it refers to a single completed reaction: I was surprised when I saw her...

Because the speaker is talking about one specific moment in the past.

• όταν = when
• είδα = aorist of βλέπω (I saw)

So όταν την είδα means when I saw her in a particular instance.

If the sentence were about repeated past events, Greek might use a different tense, but here it is clearly one event:

• I was surprised
• when I saw her
• at that moment

Την is the direct object clitic pronoun meaning her.

So:

• είδα = I saw
• την είδα = I saw her

Greek usually places these weak object pronouns before the verb:

• τον είδα = I saw him
• την είδα = I saw her
• το είδα = I saw it

Because Greek object pronouns are normally clitics that go before the finite verb.

English says:

• I saw her

Greek says:

• την είδα

This is one of the most basic word-order differences English speakers have to get used to.

Here it means wearing red lipstick or with red lipstick on.

Literally, με often means with, but in this sentence it describes appearance:

• την είδα με κόκκινο κραγιόν = I saw her with red lipstick on

So με is not really instrumental here. It is more like describing how she looked at that moment.

Comparable patterns:

• με γυαλιά = wearing glasses / with glasses
• με καπέλο = wearing a hat / with a hat on

Because in this kind of expression Greek often omits the article when describing what someone is wearing or a visible feature.

So:

• με κόκκινο κραγιόν = with red lipstick on

This sounds natural and idiomatic. It is similar to how Greek can say:

• με μαύρα ρούχα = in black clothes
• με γένια = with a beard
• με κοντά μαλλιά = with short hair

Adding an article would usually change the feel or point to something more specific.

It is in the accusative, because modern Greek με takes the accusative.

• με κόκκινο κραγιόν
• με τον φίλο μου
• με μια τσάντα

The adjective κόκκινο agrees with κραγιόν.

Κραγιόν is neuter, so the adjective must also be neuter:

• κόκκινο κραγιόν = red lipstick

That is why it is κόκκινο, not κόκκινη or κόκκινος.

Agreement:

• masculine: κόκκινος
• feminine: κόκκινη
• neuter: κόκκινο

In this sentence, κραγιόν clearly means lipstick.

It can sometimes be used a little more broadly in everyday speech for cosmetic color products, but the normal meaning is lipstick. Here, with κόκκινο, there is no ambiguity: red lipstick.

Γιατί here means because.

So:

• γιατί συνήθως δεν βάφεται καθόλου
• because she usually doesn’t wear makeup at all

Greek γιατί can mean both why and because, depending on context.

Here it cannot mean why, because it is introducing the reason for the surprise.

Συνήθως means usually.

In this sentence:

• γιατί συνήθως δεν βάφεται καθόλου
• because she usually doesn’t wear makeup at all

Its position is very natural. Greek adverbs like συνήθως are fairly flexible, but they are often placed before the verb or before the negative + verb group.

Because βάφεται comes from βάφομαι, which here means to put on makeup / to wear makeup.

This is very important:

• βάφω = I paint, dye, color something
• βάφομαι = I put on makeup / I dye my hair / I make myself up

So δεν βάφεται means:

• she doesn’t put on makeup
• more naturally, she doesn’t wear makeup

This is another case where Greek uses a mediopassive form with an active/reflexive meaning in English.

Historically and structurally, it is related to that idea, but in normal usage it is simply the standard verb for wearing makeup / putting makeup on.

So you should not translate it word-for-word every time. In this sentence, the natural meaning is:

• she usually doesn’t wear makeup at all

Depending on context, βάφομαι can also mean:

• I dye my hair
• I put makeup on
• I get made up

Because it expresses a general habit, not a single past event.

The structure is:

• I was surprised — one past event
• because she usually doesn’t wear makeup at all — a general fact/habit

So the present tense is perfectly natural. English does the same thing:

• I was surprised because she usually doesn’t wear makeup.

With negation, καθόλου means at all.

So:

• δεν βάφεται καθόλου = she doesn’t wear makeup at all

This is a very common pattern:

• δεν πεινάω καθόλου = I’m not hungry at all
• δεν μου αρέσει καθόλου = I don’t like it at all

Without negation, καθόλου can sometimes have other uses in colloquial speech, but here the meaning is straightforward: not at all.

In the full sentence, the meaning is softened by συνήθως:

• συνήθως δεν βάφεται καθόλου
• she usually doesn’t wear makeup at all

So it does not mean an absolute never. It means that as a rule, she goes without makeup, which is why the red lipstick was surprising.

It specifically points to red lipstick, not makeup in general.

The contrast is:

• at the surprising moment, she had red lipstick on
• normally, she doesn’t wear makeup at all

So the lipstick is the visible detail that triggered the speaker’s surprise.

The given word order is completely natural:

• Ξαφνιάστηκα όταν την είδα με κόκκινο κραγιόν, γιατί συνήθως δεν βάφεται καθόλου.

Greek word order is flexible, but this version is smooth and neutral. It presents the information in a clear sequence:

1. reaction: Ξαφνιάστηκα
2. moment: όταν την είδα με κόκκινο κραγιόν
3. explanation: γιατί συνήθως δεν βάφεται καθόλου

You could move things around for emphasis, but this is a standard everyday phrasing.

Yes.

• Ξαφνιάστηκα = I was surprised / I got startled / it caught me off guard
• έμεινα έκπληκτος/έκπληκτη = I was astonished / amazed

In this sentence, Ξαφνιάστηκα sounds very natural because the speaker is reacting to something unexpected but not necessarily shocking. It is a good fit for seeing someone in an unusual look.

Usually, yes.

The clause:

• γιατί συνήθως δεν βάφεται καθόλου

shows that the speaker knows her usual habits well enough to compare this moment with her normal appearance. So the sentence naturally suggests some familiarity, even if it does not explicitly say what the relationship is.