Can't trigger Jio's fourteen heart event

I searched this sub but only found one post from a few years ago, but sorry if this has been asked recently/is redundant.

He comes home around 9:50 and heads straight to bed on the 1st of the season, but the wiki says his fourteen heart event triggers between 12am-2am. I tried blocking his path to bed, but he just did that little fast run thing lol

Truly dying to see it bc I refuse to read spoilers, pls help