International Dateline Confusion

I'm about to get my masters in computer science and I still get confused when I book a flight across the international dateline. I'm trying to book a flight from Tokyo to Maui and it is very confusing. I think I'll end up choosing a flight from Tokyo to Seoul to Honolulu to Maui. The part that confuses me is the timing. Somehow I fly out at 8pm on the 18th from Tokyo and land in Maui at 2pm on the 18th. I get that I'm flying over the international date line, it's still just confusing. Anyway, I'll learned that I am dumb today.