I was out for the day and came back to find this discussion over the question I raised. I'm so pleased!
I, too, thought JOI died on April Fool's Day, based on the conversation b/w Hal and Orin. And I knew it was the Year of the Trial Sized Dove Bar from a few different places in the book - I think that seems pretty definite. For example, on pg. 993, in the footnotes, it says that JOI died during the post-production of Infinite Jest, which is dated as Year of the TSDB. And all other references seems to match up with this date. I can look through my notes and find the exact pages if it will help.
It's really two references to the year of the DAU that confuse me:
1) Pg. 142 - August DAU was 4 years after JOI killed himself
2) Pg. 249 - On Nov 5, DAU, Hal says his father died (or more likely, his father's funeral was held) 4 years and 216 days prior.
If this was the case, that DAU was 4 years after TSDB, Hal wouldn't be 17 - he'd be 16. He was 11 in the year of the Tucks..., then in 7th grade in the year of the Perdue WonderChicken, but he was about to graduate in the year of Glad, at 18, which would have meant he skipped a year and a grade somewhere. Most importantly, it doesn't match up with the chronology on page 223.
My best guess is that DFW did it on purpose, to play with memory, time, and chronology, the way he does throughout the rest of the book. I think the person who quoted Hamlet was spot on. But it's possible he made an error along the way, since he changed Hal's age in the professional conversationalist scene - Hal had initally been about to turn 11, I think it was, in earlier editions, but in the 2006 reissue, Hal was now turning 13.
Anyway. I'm so happy people responded to this!
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