Where you just want to react as you would, regardless of what you may assume is the desired response to their call. It's like I feel that i let them down whenever i dont give the response i believe they are looking for.
i personally feel let down and get a very empty feeling when it seems like someone is trying to tell me just what i want to hear. i want to be enthralled, confused, surprised, enriched, or even underwhelmed by something from them that i did not expect to hear. so in your situation, i would take every opportunity to avoid what you 'think' they 'want to hear.' if they really knew exactly what they wanted to hear, then there are some chat bots that would be a better fit for them