A conversa com a Ana nunca é chata, porque ela faz muitas perguntas interessantes.

In Portuguese, conversa is a feminine noun, so it takes the feminine article a.

• a conversa = the conversation (feminine)
• o livro = the book (masculine)

Unfortunately, grammatical gender is mostly arbitrary and has to be learned with each noun. A useful tip:

• Many nouns ending in -a are feminine (a casa, a conversa, a mesa),
  but there are exceptions (o problema, o mapa, etc.).

So you should learn it as a package: a conversa (feminine).

In European Portuguese, it is very common to use the definite article before a person’s first name in everyday speech:

• a Ana
• o João
• a Maria

It does not mean anything like “the Ana” in English; it’s just a normal, natural way of referring to people.

Notes:

• This use is much more common in Portugal than in Brazil.
• You can see it in many contexts:
  
  • Falei com a Ana ontem. = I spoke with Ana yesterday.
  • O Pedro chegou. = Pedro arrived.

So a conversa com a Ana literally has a twice: one for conversa and one for Ana.

The preposition com (with) does not normally contract with the definite article in modern Portuguese the way some other prepositions do.

Compare:

• de + a → da (from/of the – feminine)
• em + a → na (in/on the – feminine)
• a + a → à (to the – feminine)

But:

• com + a → com a (no contraction)
• com + o → com o

So com a Ana is perfectly regular: com + a Ana. There is no contraction here.

In Portuguese, adverbs like nunca (never) usually go before the main verb:

• Ela nunca é chata. = She is never boring.
• Eu nunca como carne. = I never eat meat.

Putting nunca after é ( é nunca chata ) sounds unnatural or emphatic at best, and in this specific sentence it would be odd.

So the neutral, correct word order is:

A conversa com a Ana nunca é chata…

Adjectives in Portuguese must agree in gender and number with the noun they describe.

• a conversa is feminine singular
• therefore the adjective must also be feminine singular: chata

Examples:

• A conversa é chata. (feminine singular)
• O filme é chato. (masculine singular)
• As conversas são chatas. (feminine plural)
• Os filmes são chatos. (masculine plural)

So chata matches a conversa.

Formally, ela means she, referring to a feminine person or noun. In this sentence:

• ela clearly refers to a Ana (a person), so it means she.

However, Portuguese does not have a separate word for it. Often:

• ele (he) can mean it for masculine nouns.
• ela (she) can mean it for feminine nouns.

For example:

• A mesa é nova. Ela é bonita.
  = The table is new. It is beautiful. (literally: She is beautiful, because mesa is feminine)

In your sentence, ela is naturally she = Ana.

Both are possible, but they have slightly different nuances.

• fazer perguntas = to ask questions (literally: to make questions)

  • Ela faz muitas perguntas. = She asks many questions.

• perguntar muito = to ask a lot, with more focus on the action of asking itself, and not on the quantity of questions as individual things.

In this sentence, fazer muitas perguntas emphasizes that she produces many individual questions. It’s a very common, natural collocation:

• Ele faz sempre perguntas difíceis.
• Os alunos fizeram poucas perguntas.

Muito changes form depending on gender and number, because it can function like an adjective/quantifier:

• masculine singular: muito
• feminine singular: muita
• masculine plural: muitos
• feminine plural: muitas

Since perguntas is feminine plural:

• muitas perguntas = many questions

More examples:

• muito trabalho (masc. sing.) = a lot of work
• muita água (fem. sing.) = a lot of water
• muitos livros (masc. pl.) = many books
• muitas pessoas (fem. pl.) = many people

Adjectives must agree in gender and number with the noun:

• pergunta – feminine singular
• perguntas – feminine plural

So:

• singular: uma pergunta interessante (one interesting question)
• plural: muitas perguntas interessantes (many interesting questions)

muitas pergunta interessante would be incorrect because:

• muitas is plural, but pergunta and interessante are singular. They all need to match: muitas / perguntas / interessantes.

Portuguese uses ser and estar (both mean to be) differently:

• ser (é) is used for more permanent/general characteristics.
• estar (está) is used for temporary states/conditions.

Here, we are expressing a general truth about conversations with Ana:

• A conversa com a Ana nunca é chata.
  = Conversations with Ana are never boring (in general; as a characteristic).

Using está (nunca está chata) would sound like we are talking about a specific conversation at a particular moment.

Also, Portuguese does not use a continuous form for this general meaning (you don’t say nunca está a ser chata here).

In European Portuguese, chato / chata often means:

• boring, tedious, annoying, a pain

In this sentence:

• a conversa nunca é chata = the conversation is never boring / never a drag.

About politeness:

• Ele é um bocado chato. can be mild (a bit annoying) or quite negative, depending on tone.
• Between friends it can be relatively soft, like “kinda annoying” or “a bit of a pain”.

There are also synonyms:

• aborrecido / aborrecida (more formal or neutral: boring)
• uma seca (slang: a drag, really boring) → A conversa nunca é uma seca.

So chata here is informal/colloquial but not very strong; context and tone decide how rude it sounds.

In Portuguese, it is very common (and usually recommended) to put a comma before porque when it introduces a full clause of reason that explains the first part of the sentence:

• A conversa com a Ana nunca é chata, porque ela faz muitas perguntas interessantes.
  = The conversation with Ana is never boring, because she asks many interesting questions.

The comma separates:

1. main clause: A conversa com a Ana nunca é chata
2. subordinate clause of reason: porque ela faz muitas perguntas interessantes

Writing it without the comma is sometimes seen, but with the comma is clear and standard here.

They look similar but work differently:

1. porque (one word)

   • most common
   • means because
   • introduces a reason
   • Não vou sair porque está a chover. = I’m not going out because it’s raining.

2. por que (two words)

   • literally for what/which
   • often used in questions or indirect questions
   • Por que estás triste? = Why are you sad?
   • Não sei por que ele saiu. = I don’t know why he left.

3. porquê (with accent, usually noun)

   • means reason (as a noun)
   • usually appears with an article or determiner
   • Não entendo o porquê. = I don’t understand the reason.
   • Há sempre um porquê. = There is always a reason.

In your sentence we are giving a reason, so we use porque: … nunca é chata, porque ela faz….