I am doing something like that myself as a side project, not exactly as "AI" more as voice interface responding to voice commands that uses humor and character voices to reply. In way, the problem of bots is actually "AI".
You can create a more flexible and lively experience if you put "AI" aside and really think of how people interact and create responses that are not based on "mean" values, but on real conversations. You don't even need the whole AI backend, you can just use javascript, audio files with or without accompanying text. Because so much of the conversation is bland, having a "voice" will make a huge difference.
AI developers should consider collaborating with writers and comedians:)