I'm thinking of asking someone who had to cancel our date to pay half
Why should he have to pay half when he wasn't there?
Because I know he never values time, and he cancels dates last minute
If he cost you money for the canceled date, it's appropriate to ask him to reimburse you for your money and time. If he is a moral person, he should compensate you and apologize for canceling on you because it's not right to cancel on someone for no good reason.
He is a total dickhead who never shows up on time anyway.
I'm really sorry you had to go through such annoying experiences with him! It's completely up to you to try and get him to pay, because it was an obligation for the both of you! Hope you find a better man xo