For number 7, go to Jina's room and click on the wine bottle at noon.
For number 20, go to the storage room at school at morning after getting Sena to level 1.
That's definitely it though. I would just continue the story for now with every girl. Maybe there's a requirement I don't know. It triggered for me pretty early on though after getting her. Maybe the new update wants you to do something else to trigger it. I will try replaying the game and see for myself