I am not sure I see most of this as a problem. For an agent you would want to write some longer instructions than just "book me an aniversery dinner with my wife".
You would want to write a couple paragraphs outlining what you were hoping to get (maybe the waterfront view was the important thing? Maybe the specific place?)
As for booking a babysitter - if you don't already have a specific person in mind (I don't have kids), then that is likely a separate search. If you do, then their availability is a limiting factor, in just the same way your calendar was and no one, not you, not an agent, not a secretary, can confirm the restaurant unless/until you hear back from them.
As an inspiration for the query, here is one I used with Chat GPT earlier:
>I live in <redacted>. I need a place to get a good quality haircut close to where I live. Its important that the place has opening hours outside my 8:00 to 16:00 mon-fri job and good reviews.
>
>I am not sensitive to the price. Go online and find places near my home. Find recent reviews and list the places, their names, a summary of the reviews and their opening hours.
>
>Thank you