The confrontation of Eric and Dexter at a low dex score blocks the milk delivery scene with Annie. The Eric-Dexter scene pops up every time when the MC goes to school, apparently as long as your dex is too low.
Cross story issues will be fixed in a future update. Until then, it is recommended that you finish each story line before moving to the next to minimize issues. This is an alpha, there will be bugs between versions.
