Age 748 or so: while Gohan’s had an easier job raising Goku since the traumatic head injury, the boy still has a nasty habit of absorbing Bruits Waves through his eyes. Gohan warns him to stay indoors whenever Bruits levels exceed 17 million zeno, but one night... #HistoryofEver
After this (surely the most tragic midnight potty trip in history), Goku is left all on his own up in the mountains, miles from civilization. He inherits Gohan’s magic staff, plus a weird ball Gohan found one day. Goku starts talking to this memento as if it were Gohan himself 
Prior to his death, Gohan had trained Goku in the martial arts, including his trademark Rock-Paper-Scissors technique. Daizenshuu 7’s technique dictionary also speculates that Goku might’ve received some ki training from Gohan, which is how he mastered the Kamehameha so fast.
While Goku never saw another human when living with his grandfather, Gohan did tell him to treat women nicely. And though Gohan didn’t teach young Goku anything of female anatomy, he did apparently explain what “bloomers” are.
(Or so it seems from Goku’s reaction to Bulma’s name. Viz makes Goku’s comments more explicit, while in Japanese he merely calls it a “funny name”, so maybe he doesn’t actually know about Japanese gym shorts terminology)
Somewhat on that note: Goku was in the habit of sleeping with his head on Gohan’s crotch, as we see when he tries the same thing with Bulma. Yep, good ol’ early DB.
More gaps in Goku’s education: not knowing about baths or the sea. On the other hand, he’s apparently familiar with Buddhist prayer beads and stainless steel (he compares his body to the latter; this is changed to simply “steel” in the anime, and left out of Viz entirely)
The date of Gohan’s death isn’t specified beyond being prior to the series’ start. Goku retains no memories of his time in Ape mode, and doesn’t realize the true identity of the “monster” who killed his grandpa until seeing Vegeta’s transformation causes him to connect the dots.
Meanwhile, Gohan receives first-class treatment in the afterlife, keeping his body like the other dead martial arts masters, and getting lucrative contracting work from time to time. Goku himself will later get much the same deal when he dies (minus the contracting gigs)
Besides fighting for Baba, the Wedding Dress filler arc shows another of Gohan’s post-death gigs: serving as personal assistant to Annin as she tends her magic furnace. No wonder he doesn’t want to come back to life!
On Tuesday: crybaby!
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