How would you feel if you found out he'd broken it for you? Jason thinks it's a proof of love. What he wants is for Bruce to reassure him that Bruce loves him, and for any number of reasons - top of which is having become convinced that Bruce never loved him enough - he picks the one most impossible choice to give Bruce. Jason is all but saying that he finds dying a preferable option to living if Bruce doesn't love him, here. He's not thinking rationally, he's making one last desperate stand and he's set himself up to fail. I don't think there's any surprise involved; he wouldn't be crying if he was.
Then there's the issue of Jason thinking that some criminals should be killed, and wanting Bruce to admit it. I suspect the reason why he hasn't killed Joker is that he wants Bruce to kill him. Pre-Countdown at least, that was Jason's opinion on how the aftermath of his death should have gone. (How Earth-51 made him change his mind is anyone's guess since DC isn't giving much clues, but the visit at least seemed to have a couple of consequences on his opinion on a short term.)