Learn Hardcore Portuguese (Portugal): Eu tentei pedir desculpa, mas ele ainda não conseguiu perdoar-me. - I tried to apologise, but he still hasn’t managed to forgive me.

desculpar by itself usually means to forgive / to excuse someone:
- Ele desculpou o amigo. = He forgave/excused his friend.
pedir desculpa (or pedir desculpas) means to apologize, to say sorry:
- Eu tentei pedir desculpa. = I tried to apologize.

So in your sentence, the idea is that I tried to apologize, not I tried to forgive.

In Portugal, is it better to say pedir desculpa or pedir desculpas?

In European Portuguese, both pedir desculpa (singular) and pedir desculpas (plural) are used and understood, but:

pedir desculpa is more common and feels a bit more natural/neutral in Portugal.
pedir desculpas is very common in Brazilian Portuguese, and is also fine in Portugal, just slightly less typical.

So for European Portuguese, pedir desculpa is a very good default choice.

Why is it tentei pedir and not tentei de pedir or tentei a pedir?

The verb tentar in Portuguese is followed directly by an infinitive, without a preposition:

tentar + infinitive
- Eu tentei pedir desculpa. ✔️
- Eu tentei ajudar. ✔️

Forms like:

tentei de pedir ✖️
tentei a pedir ✖️

are incorrect in standard Portuguese.

Some other verbs do need a preposition (e.g. começar a fazer, ajudar a fazer), but tentar does not take a or de before an infinitive.

What tense is tentei, and why not something like tenho tentado (have tried)?

Tentei is the pretérito perfeito do indicativo (simple past), used for completed actions in the past:

Eu tentei pedir desculpa.
= I tried (at some point, one or more times) to apologize.

The English translation often uses I tried or I’ve tried, but Portuguese doesn’t normally use tenho tentado in this kind of sentence unless you want to stress repeated/ongoing attempts over time:

Tenho tentado pedir desculpa.
= I’ve been trying to apologize (over a period, repeatedly).

So tentei is the natural and simplest way to express a past attempt, without a strong emphasis on duration or repetition.

Why is conseguiu used? Does não conseguiu perdoar-me mean something different from não me perdoou?

Yes, there is a nuance:

Ele ainda não conseguiu perdoar-me.
Literally: He still hasn’t managed to forgive me.
→ Emphasizes difficulty or inability to forgive, even if he perhaps wants to.
Ele ainda não me perdoou.
Literally: He still hasn’t forgiven me.
→ More neutral: the fact is simply that forgiveness hasn’t happened.

So não conseguiu perdoar-me suggests some kind of internal struggle or obstacle that is preventing him from forgiving, rather than just a bare statement of fact.

Why is the pronoun attached to the infinitive (perdoar-me) instead of before the verb, like me perdoar?

This is a key difference between European and Brazilian Portuguese.

In European Portuguese, clitic pronouns (me, te, se, o, a, etc.) are often attached to the end of infinitives and main verbs (enclisis), especially in affirmative sentences:

perdoar-me
ajudar-me, ver-te, dizer-lhe

So:

Ele ainda não conseguiu perdoar-me. ✔️ (very natural in Portugal)

In Brazilian Portuguese, me perdoar is more common in everyday speech:

Ele ainda não conseguiu me perdoar. (Brazil)

In European Portuguese, you can also move the pronoun before the main conjugated verb in contexts where proclisis is triggered:

Ele ainda não me conseguiu perdoar. ✔️
(here não attracts the pronoun me before conseguiu)

But perdoar-me is perfectly standard and very typical in Portugal, especially after an infinitive with conseguir, querer, tentar, etc.

Why is it perdoar-me and not something like perdoar eu or perdoar a mim?

In Portuguese you generally use clitic object pronouns (me, te, o, a, lhe, nos, etc.) rather than stressed forms (eu, mim, ti) after verbs, unless you want to add emphasis.

Normal object form: me
- perdoar-me = to forgive me

Using eu here would be ungrammatical:

perdoar eu ✖️ (incorrect)

A mim is possible but is used for emphasis or contrast, and it typically adds to the clitic, not replaces it:

perdoar-me a mim
= to forgive me (as opposed to someone else), very emphatic.

So in normal speech, perdoar-me is the correct and natural form.

Is it necessary to say Eu at the beginning, or could I just say Tentei pedir desculpa?

You can absolutely drop Eu:

Eu tentei pedir desculpa…
Tentei pedir desculpa…

Both are correct. Portuguese is a pro-drop language: subject pronouns (eu, tu, ele, etc.) are often omitted because the verb ending (tentei) already shows the person (eu).

You normally include Eu when you want to:

add emphasis or contrast (e.g. Eu tentei, mas ele não quis…)
be especially clear in a complex or ambiguous context.

In your sentence, both versions are natural in European Portuguese.

Can I change the order in ele ainda não conseguiu perdoar-me? For example, ele não conseguiu ainda perdoar-me?

Word order is quite flexible here, but not every option is equally natural.

Very natural:

Ele ainda não conseguiu perdoar-me. ✔️ (most common)
Ele ainda não me conseguiu perdoar. ✔️ (equally fine, slightly different focus)

Also acceptable, but slightly more marked/stylistic:

Ele não conseguiu ainda perdoar-me. ✔️ (emphasizes ainda a bit more)

To avoid:

Ele ainda conseguiu não perdoar-me. ✖️
This would mean something like He still managed not to forgive me, which is a different meaning.

So your original word order is the most straightforward and idiomatic.

Could I say Eu tentei desculpar-me instead of Eu tentei pedir desculpa? Is there any difference?

You can say tentei desculpar-me, but there’s a nuance:

pedir desculpa
= to apologize, to say sorry (what you normally do in everyday situations)
desculpar-se
= to excuse oneself, to justify oneself, to get oneself forgiven
Often suggests explaining or defending your actions.

So:

Eu tentei pedir desculpa.
= I tried to apologize (I tried to say “sorry” to him).
Eu tentei desculpar-me.
= I tried to get myself excused / tried to justify myself / tried to get forgiven.

In normal conversation about saying sorry to someone, pedir desculpa is the safest, most neutral European Portuguese choice.