Non oso chiedere.

Oso is the 1st person singular present indicative form of osare, which means to dare.

So:

• osare = to dare
• oso = I dare

In Non oso chiedere, oso means I dare, and the non makes it negative.

Italian often drops subject pronouns when they are not needed.

The verb ending already tells you the subject:

• oso = I dare
• the -o ending shows it is io

So Non oso chiedere is perfectly natural.
You could say Io non oso chiedere, but adding io usually gives extra emphasis, like I don’t dare ask.

In Italian, non normally goes directly before the conjugated verb to make it negative.

So:

• oso = I dare
• non oso = I do not dare / I don’t dare

This is the standard pattern in Italian:

• non so = I don’t know
• non voglio = I don’t want
• non posso = I can’t

Because osare is followed by another verb in the infinitive.

This works much like English:

• I dare ask
• I don’t dare ask

In Italian:

• oso chiedere
• non oso chiedere

So osare + infinitive is the normal structure.

No. With osare, you normally use the infinitive directly, without a or di.

So the natural form is:

• Non oso chiedere

Not:

• Non oso a chiedere
• Non oso di chiedere in normal modern usage

A learner may want to add a preposition because English has to ask, but in Italian the infinitive is already just chiedere.

Chiedere usually means to ask, but depending on context it can also mean to ask for or to request.

For example:

• chiedere una domanda is not natural Italian
• chiedere qualcosa = to ask for something
• chiedere a qualcuno = to ask someone
• chiedere se... = to ask whether...

In Non oso chiedere, the exact nuance depends on context:

• I don’t dare ask
• I don’t dare ask for it
• I don’t dare ask the question

Yes, osare is correct and natural, but it can sound a little more direct or literary than some everyday alternatives.

A very common alternative is:

• Non ho il coraggio di chiedere = I don’t have the courage to ask

Both are good, but:

• Non oso chiedere = shorter, more compact
• Non ho il coraggio di chiedere = a bit more explicit and conversational

Normally, Non oso chiedere is the natural order.

Italian usually places non before the conjugated verb, so this is the standard structure.

If you move things around, you may change the meaning or make the sentence sound unnatural. For a learner, the safest pattern is:

• non + conjugated verb + infinitive

So:

• Non oso chiedere

You just change the form of osare.

Present tense:

• non oso chiedere = I don’t dare ask
• non osi chiedere = you don’t dare ask
• non osa chiedere = he/she/it doesn’t dare ask
• non osiamo chiedere = we don’t dare ask
• non osate chiedere = you all don’t dare ask
• non osano chiedere = they don’t dare ask

Notice that chiedere stays in the infinitive.

A useful thing to know is that ch before e or i in Italian is pronounced like a hard k.

So chiedere does not start like English cheese.
It starts with a k sound.

A rough guide is:

• chiedere ≈ KYEH-deh-reh
• oso ≈ OH-zoh

The exact pronunciation is more Italian than the English approximation, but the important point is that ch here is hard, not soft.