Wasn't it disclosed through the Ashley Madison hack that they were employing bots (and real people) to keep the clients busy and lure them into buying more "chatting privileges" (number of messages etc.?

So this has already happened to some degree. As AI (aka humans teaching computers) to make for better "hungrier" chatboxes, with the escalation (buy more messages, send client to next tier), sell a "more personalized package" (to use the parent comment of his friend).

This could do a nice Black Mirror episode. Like the one where she lost her husband, her friend registered for the Tier1 service and it went on from that..