Learn Hardcore Spanish (Latin America): Ojalá no te hubieras preocupado tanto por esa equivocación pequeña. - I wish you hadn’t worried so much about that small mistake.

In this sentence it introduces a wish about something in the past that did happen, but the speaker wishes it hadn’t. So it corresponds to English “I wish…” (not “hopefully”) in this context.

Ojalá + subjunctive = wish
With a past subjunctive (like hubieras preocupado), it usually expresses regret about a real past situation.

So:

Ojalá no te hubieras preocupado…
≈ I wish you hadn’t worried… (but you did worried).

Why is there no que after ojalá? Can I say ojalá que no te hubieras preocupado?

Yes, you can say both:

Ojalá no te hubieras preocupado tanto…
Ojalá que no te hubieras preocupado tanto…

In modern Spanish (including Latin America):

With or without “que” are both correct.
In everyday speech, many people omit “que”: Ojalá no pase eso, Ojalá haya dinero, etc.
Adding que sometimes sounds a bit more emphatic or formal, but the meaning is the same here.

So the sentence is fine as written, and adding que would also be correct.

Why is it hubieras preocupado and not habías preocupado?

Because after ojalá (expressing a wish), Spanish requires the subjunctive, not the indicative.

Habías preocupado = past perfect indicative (you had worried – just stating a fact).
Hubieras preocupado = past perfect subjunctive (you had worried in a hypothetical / wished-about sense).

Structure used here:

Ojalá + past perfect subjunctive (hubieras + participle)
→ wish or regret about a completed action in the past.

So:

Habías preocupado tanto = You had worried so much. (fact)
Ojalá no te hubieras preocupado tanto = I wish you hadn’t worried so much. (regret)

What’s the difference between hubieras and habrías here? Could I say Ojalá no te habrías preocupado tanto?

In this kind of sentence, habrías is not natural.

Compare:

Ojalá no te hubieras preocupado tanto.
= I wish you hadn’t worried so much.
→ Standard and correct: ojalá + past perfect subjunctive.
Ojalá no te habrías preocupado tanto.
This sounds wrong or very odd to native speakers; we don’t normally use habrías (conditional perfect) after ojalá for this meaning.

Use:

hubieras / hubieses preocupado (subjunctive), not habrías preocupado (conditional), after ojalá when expressing regret about a past reality.

Why do we need te in no te hubieras preocupado? What’s the difference between preocupar and preocuparse?

Spanish distinguishes:

preocupar (a alguien) – non‑reflexive
- Means “to worry (someone), to cause worry to someone.”
- Example: Esa noticia te preocupa. = That news worries you.
preocuparse (por algo) – reflexive
- Means “to worry (oneself), to be worried.”
- Example: Te preocupas demasiado por todo. = You worry too much about everything.

In your sentence:

no te hubieras preocupado uses preocuparse (reflexive), so we need the reflexive pronoun te.
Without te (no hubieras preocupado) it would mean “you hadn’t worried someone else,” which doesn’t fit the intended meaning.

So te shows that you were the one feeling worried, not causing worry to others.

Why is the pronoun placed like no te hubieras preocupado and not no hubieras te preocupado or no hubieras preocupado te?

In compound tenses with haber (he, había, hubiera, etc.), object and reflexive pronouns go before the conjugated verb, not between haber and the participle:

✅ no te hubieras preocupado
❌ no hubieras te preocupado
❌ no hubieras preocupado te

General rule:

Negation + pronoun(s) + conjugated verb + participle
- no te habías preocupado
- no me he dado cuenta
- no se habría ido

Why preocupado and not preocupada? What happens if I’m talking to a woman?

The past participle preocupado / preocupada agrees in gender and number with the subject, which is tú.

Talking to a man:
Ojalá no te hubieras preocupado tanto… (preocupado)
Talking to a woman:
Ojalá no te hubieras preocupado tanto… (preocupada)

In writing, the gender is often not indicated unless context makes it clear, but in speech you would say preocupado or preocupada depending on who tú is.

Why is it tanto and not tan? What’s the difference?

Tan and tanto are different:

tan = “so” before adjectives/adverbs
- tan preocupado = so worried
- tan rápido = so fast
tanto = “so much” / “so many,” before nouns or as an adverb of quantity
- tanto trabajo = so much work
- tanto (alone) = so much / so (much)

In no te hubieras preocupado tanto:

tanto modifies the verb preocuparse → hadn’t worried so much.
If you wanted tan, you’d say:
Ojalá no hubieras estado tan preocupado. = I wish you hadn’t been so worried. (here tan modifies the adjective preocupado).

Why esa equivocación pequeña and not esa pequeña equivocación? Is there a difference?

Both orders are grammatical, but there’s a nuance:

esa equivocación pequeña
- Adjective after the noun: usually more neutral / descriptive.
- Emphasizes the kind of mistake: a mistake which is small.
- Sounds fine, but many speakers would more naturally say esa pequeña equivocación in this exact context.
esa pequeña equivocación
- Adjective before the noun: often more subjective, emotional, or evaluative.
- Here it can suggest: that little mistake (and it really wasn’t a big deal).
- This is very common in Spanish with adjectives like pequeño, gran(de), pobre, viejo, simple when adding a certain emotional tone.

Meaning-wise they’re very close; style and emphasis change slightly. In everyday speech, esa pequeña equivocación may sound a bit more idiomatic.

What’s the difference between equivocación and error here? Could I say ese pequeño error instead?

Yes, you could say:

Ojalá no te hubieras preocupado tanto por ese pequeño error.

Differences:

equivocación
- Often a slip, mistake, misunderstanding, usually less serious.
- Common in everyday talk when we want to sound softer or less harsh.
error
- Also “mistake” or “error,” but can sound a bit more serious, technical, or formal, depending on context.
- Very common in all registers too.

In this sentence, both esa equivocación pequeña and ese pequeño error are natural.
Using equivocación reinforces the idea of a minor, forgivable slip, which matches the context of “you shouldn’t have worried so much.”

Could I say Ojalá no te preocuparas tanto por esa equivocación pequeña instead? How would the meaning change?

You can, but the meaning shifts:

Ojalá no te hubieras preocupado tanto…
- Refers to a specific past situation (a particular time when you worried).
- Implies: you did worry, and I regret that.
Ojalá no te preocuparas tanto…
- Uses the imperfect subjunctive with present/future reference.
- Often means a general or habitual situation:
  I wish you wouldn’t worry so much (in general / as a habit) about that small mistake.
- It can still be about something ongoing now (you keep worrying about it).

So:

hubieras preocupado → regret about a completed past action.
preocuparas → wish about a present or repeated behavior.

What’s the difference between hubieras preocupado and hubieses preocupado?

They are just two forms of the same tense: the past perfect subjunctive.

hubieras preocupado
hubieses preocupado

In meaning and use, they are identical. The only difference is style and regional preference:

In most of Latin America and much of Spain, -ra forms (hubieras) are much more common in speech.
-se forms (hubieses) sound a bit more formal or literary, but are still correct.

So you could also say:

Ojalá no te hubieses preocupado tanto por esa equivocación pequeña.

Same meaning, just a slightly different style.