You have to click on that human or person symbol at the top right of the screen and then go to the "Characters" section. Click on the box called "Side Events" for each girl. You can see what you need to do next to trigger a new event. If it says "Chat: Available" Then chat with them some more to trigger new events and dialogue. If it say "Chat:WIP" that means that area is done for now. Focus on other areas. If it says "Practice: Available" practice with her in that area (color) Red practice color means train with her in Fitness. "Beach: Available" means you can go to the beach with her at certain times to trigger more events of new dialogue. If something says "WIP" you can still do i, you just wont trigger a new scene or dialogue. I hope that's what you meant.