I wouldn't call it a "major" plot hole, its really rather minor, they could have cut out the conversation and removed the hole completely, but that would take away from the movie.
However, I have another possible explanation that changes quite a lot about how many people perceive the movie, but I have been thinking, and I think it makes sense. Here goes:
Because Chiaki AND Makoto were both capable of time travel, their time jumps affected each other, and Chiaki, was aware of most (if not, all) of Makoto's leaps. Notice that when Chiaki asked her out on the bike ride, no matter what Makoto did, she was not able to change it short of avoiding him completely, because Chiaki was aware that she jumped back to change it. Then right before the bike accident at the end, Chiaki asks Makoto if she is time leaping, but she panics and jumps back again and easily changed the conversation this time in contrast to the conversation before. At that point I think Chiaki already knew it was her, and he didn't ask the second time because he already got the answer he wanted. Which explains why Makoto can remember making the last time leap. It also changes the ending somewhat, as Chiaki was probably still aware that he has already asked Makoto out, and chose to refrain from repeating himself for whatever reason, just to be dramatic most likely, or something else, who knows.
Anyway, that's my take. Not what I originally thought when I watched the movie last night, just an idea that developed later. Originally I assumed he Chiaki jump to before Makoto used her last time leap but after the point where she jumped back to, which sounds plausible, but doesn't really hold up to scrutiny.
Whichever explanation is used, its still a great movie. Definitely the best anime film I've seen to date.
Tell me what you think.
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