The icons don't always show because of how rpgmaker loads images. when entering a new map images are loaded and that takes time. that is also the reason why sometimes icons in the quest description don't load. so if you wait a moment after entering a new map the icons should show. For most images during animations I use a preload (otherwise images would flicker). I will search if there is a good way to also preload the iconset so that this problem can get fixed... but no promises.
Edit: checkted the save and couldn't find a problem... next interaction step with Frisha is to wait until a morning when she is talking to Dave in Emily's house and then walk in on their conversation.
It's a minor issue that can be resolved with that interaction as we've already covered, but by not doing it she goes through the motions of preparing for her date. Similarly with the dinner interaction, it's immersion breaking having them react as if it was MC's first time over after so many days have passed & other events have been completed, such as saving Emily & Frisha. Just so that we're on the same page about what I mean.
>load the save provided
>check completed quests to confirm that Saving Emily & Frisha's Date are both on the list
>(optional) leave tavern, go to Emily's house and attend dinner. The 1st scene will play out, disregarding the other events such as saving Emily & Frisha
>leave tavern and wait until next morning
>enter Emily's house and talk to Frisha, choose just say hello and she mentions how she's doing better now that she was saved from Dave
>leave house and wait until Wed/Sat noon or afternoon and check on Frisha (don't enter in the morning)
>and there she is, preparing for her date
That's the whole issue. It's not a big deal or much of a priority, but I wanted to bring it up because of the aforementioned inconsistency.