You've got to keep trying to find her.I recently restarted both because I seem to have been on the NTR route and I wanted to earn the cards I missed by completing the scenes that give them before they were added to the game. The first route I was using the in phone hints to figure out what to do and was all over the place with my tasks.
So for this one, I have been following a walkthrough and recently gotten to the first date with Jacky. It triggered the beach event and now she is avoiding me. While I know that is by design, I didn't think it would happen until after I finished all six of the dates. And because she is avoiding me, the other events that the walkthrough says are to happen, don't.
Is there a way to fix that, or do I just have to wait?
I think it's four time you have to see her avoiding you before you can move that event to the next stage where you talk to Mandy at night.
You can look for her in her room early morning, breakfast early morning, her office in the afternoon, after paying Joey on the weekend.
The goal was to show the player that Jacky was avoiding the player, but we could have done a better job of presenting that to the player.