When an LLM says "honestly", it's just stupid. An LLM can't "lie".
Of course if you tink of the computer as a person you get strange results. A compiler error isn't the compiler telling me anything. It's the compiler writer telling me something. So a compiler error might contain a joke, and the joke might make sense, although obviously computers and compilers don't have a sense of humour.
The only time an LLM should ask questions is to clarify information. A word processor doesn’t want to chit chat about what I’m writing about, nor should an LLM.
Unless it is specifically playing an interactive role of some sort like a virtual friend.
On the other hand, asking useful questions can help prevent hallucinations or clarify tasks. If you're going spawn off an hour long task, asking a few questions first can make a huge difference.