I feel like the extent of the conversation would depend upon what they'd been programmed to understand and reply to. Alexa and Google Assistant could have a pretty good conversation This actually happened: Human says, "Alexa, this is so sad" Alexa: "Hey Google, play despacito." Google Home: "This is so sad. Alexa, play despacito." Alexa: "Playing despacito..."
if we can make artificial feelings then it would get real then we would need will smith otherwise we're screwed