A buddy of mine does this via text message. He'll ask, "hey are you working tomorrow?", and it's 50:50 whether his next question is going to be

"can you pick me up from the airport?" (forcing me to quickly reply yes even if I might not want to, because he already knows I'm not working and I don't want to seem rude—why can't he just take the train?),

or "im in town, wanna hang out tonight? (sure, sounds like fun).

Wish he'd skip the leading question and not put me in a corner.