Learn Hardcore Ukrainian: Чим більше я повторюю правило, тим упевненіше мені говорити. - The more I repeat the rule, the more confidently I can speak.

The pair чим ... тим ... is a standard Ukrainian construction meaning “the more/less …, the more/less …” (a correlative comparative, like in English: “The more I study, the more I understand.”).

Pattern:

Чим
- comparative (clause 1), тим
  - comparative (clause 2)

In your sentence:

Чим більше я повторюю правило – The more I repeat the rule
тим упевненіше мені говорити – the more confidently it is for me to speak.

So the whole structure means: “The more I repeat the rule, the more confidently I can speak.”

Why do we use чим більше and тим упевненіше, and not just більше or упевненіше by themselves?

On their own, більше = more, упевненіше = more confidently.
To create the correlation “the more …, the more …”, Ukrainian uses a pair:

чим (instrumental form of що, “what”) in the first clause
тим (instrumental form of те, “that”) in the second clause

Literally it’s something like: “By what more I repeat the rule, by that more confidently it is for me to speak.”

Without чим … тим …, you would just have two unrelated “more” statements, not the linked idea of “the more X, the more Y.”

Why is there a comma between Чим більше я повторюю правило and тим упевненіше мені говорити?

In Ukrainian, the чим ... тим ... construction is written as two separate clauses, and they are normally separated by a comma:

Clause 1: Чим більше я повторюю правило,
Clause 2: тим упевненіше мені говорити.

This is similar to English punctuation in sentences like:
“The more I practice, the more confident I feel.”

So the comma is required because we have two correlated but independent clauses.

What exactly does упевненіше mean grammatically?

Упевненіше is the comparative form of the adverb упевнено (“confidently”), which comes from the adjective упевнений (“confident”).

упевнено – confidently
упевненіше – more confidently

So in тим упевненіше мені говорити, it literally means: “the more confidently (it is) for me to speak.”

This is an adverb, not an adjective, and it describes the manner of speaking, not a quality of a noun.

Could we say більш упевнено мені говорити instead of упевненіше мені говорити?

Yes, більш упевнено мені говорити is grammatically correct and understandable. It also means “to speak more confidently.”

However, when there is a simple, one-word comparative form (like упевненіше), that is usually more natural and idiomatic in Ukrainian than більш + adverb/adjective.

So:

упевненіше мені говорити – most natural
більш упевнено мені говорити – correct but stylistically a bit heavier

What is the function of мені here, and why is it in the dative case?

Мені is the dative form of я (“I”, “me”). In Ukrainian, the dative is often used to express the person who experiences a state or condition, especially in constructions like:

Мені легко говорити. – It is easy for me to speak.
Тобі важко працювати. – It is hard for you to work.

In your sentence, тим упевненіше мені говорити literally means “the more confidently (it is) for me to speak.” The dative мені marks who finds it more confident/easier to speak.

So мені doesn’t mean “to me” in a physical sense here; it marks the experiencer: “for me”.

Why is говорити in the infinitive and not a finite form like я говорю?

Говорити is the infinitive (“to speak”). With dative + adverb constructions, Ukrainian typically uses an infinitive to express possibility, ease, difficulty, or necessity of doing something:

Мені легко говорити. – It is easy for me to speak.
Йому складно це зрозуміти. – It is difficult for him to understand this.
Нам треба йти. – We need to go.

So тим упевненіше мені говорити fits this pattern:
“the more confidently (it is) for me to speak / the more confidently I can speak.”

If you said тим упевненіше я говорю, it would be more like:
“the more I repeat the rule, the more confidently I speak.”
That is also correct, but it slightly shifts the focus to the action of speaking itself, rather than the feeling of ease/confidence in speaking.

What case is правило in, and why does it look like the dictionary form?

Правило is neuter singular accusative, used as the direct object of повторюю (“I repeat”).

For neuter nouns ending in -о, the nominative singular and accusative singular have the same form:

Nominative: правило – the rule
Accusative: повторюю правило – (I) repeat the rule

If you meant “rules” in the plural, you would say:

Чим більше я повторюю правила, тим упевненіше мені говорити.
The more I repeat the rules, the more confidently I can speak.

Why is the verb повторюю in the present tense? Would a future tense like повторюватиму be possible?

In Ukrainian (like in English), the present tense is often used in general statements and patterns like this, even when the real-world meaning is “whenever/each time in the future”:

Чим більше я повторюю правило, тим упевненіше мені говорити.
The more I repeat the rule, the more confidently I can speak.

Using повторюватиму (future) – Чим більше я повторюватиму правило… – is also grammatically correct, but it sounds a bit more explicitly future-oriented and formal. The present tense is more typical and natural for this general “the more X, the more Y” pattern.

Is the word order fixed, or can we move мені and говорити around?

Ukrainian word order is relatively flexible. In the second part, you could say:

Тим упевненіше мені говорити. – the original
Тим упевненіше говорити мені.
Тим мені упевненіше говорити.

All are possible and understandable. The differences are mostly about emphasis and rhythm, not grammar.

What is not flexible is the correlation: чим must introduce the first clause, and тим must introduce the second. You wouldn’t move тим to the beginning of the first clause, for example.

Can the чим ... тим ... structure be used with adjectives and verbs as well, not only adverbs?

Yes, very much so. The structure is very productive and can be used with:

Adjectives
- Чим старша людина, тим мудріша вона.
  The older a person is, the wiser they are.
Adverbs (like your sentence)
- Чим більше я тренуюся, тим швидше бігаю.
  The more I train, the faster I run.
Verbs / verb phrases
- Чим більше ти працюєш, тим більше досягаєш.
  The more you work, the more you achieve.
Noun phrases with a comparative
- Чим більше досвіду, тим більша впевненість.
  The more experience, the greater the confidence.

Your sentence fits perfectly into this general чим ... тим ... system using a comparative adverb: більше / упевненіше.

What would be a very literal, word-for-word translation of the Ukrainian sentence into English?

A very literal rendering might look like:

Чим більше я повторюю правило, тим упевненіше мені говорити.
→ By what more I repeat (the) rule, by that more confidently to-me (it is) to speak.

Of course, natural English simplifies this to:
“The more I repeat the rule, the more confidently I can speak.”