Not fundamentally impossible. Just as a friend may know not to recommend the gig as they're aware of the breakup, so can an AI. Heck after conversing with Pi a few weeks ago, I'm fairly convinced it'd at this point be able to handle that kind of nuance if it had access to the relevant data.
"I've recognized you removed all future calendar events related to {girlfriend} and your recent text messages concerning her had a negative sentiment. Did you break up?"
Not the world I'd want to live in... but for people less concerned about their data, I can't say it wouldn't be useful!
