Mine is Clippy, but it's constantly retrieving information from the wrong word document.

"Hey, it looks like you're on holiday abroad. Would you like to take your car to the garage? The MOT expires tomorrow."

"Hey, would you like some help researching this really interesting camera equipment during working hours?"

"Hey, I see you're going to the gym. Let me remind you of all the tasks you need to do at home and now you won't have time to do: (...)"