I've noticed that some people I communicate with over chat have developed habit of actively scuttling my attempts to end chat conversations by dropping ever increasing clickbait headline / tweet style messages. It pulls me back in for a couple messages, or another 20 minutes of chatting, but it's burning me out on these chat apps.
"Ahh yeah sorry nevermind. I can work on this myself. <person known to upset me> will be presenting right before me but I'm pretty sure my presentation will blow theirs out of the water."
This is an overly simplified and contrived example. Like I said it's more likely to occur during a longer conversation, not in a quick ping for help like that. It's also typically much more subtle, and it takes many different shapes and sizes. I noticed it got more extreme the higher my position became.
For it to be effective, it requires a lot of knowledge about a person's likes, dislikes, hot buttons, etc.