All-weather means the planes are equipped with better radar systems allowing them to perform operations in poor weather and/or night operations. It’s an evolution of the night-fighter from WW2 since the radar systems on night fighters also gave them the capabilities to operate in poor weather conditions compared to the contemporary “standard” fighters.
There’s nothing wrong with just making friendly conversation, but you should not ask out random service workers because they have to be polite to the customer and it puts them in a weird spot if some stranger just asks them on a date.