I'm assuming you're talking about the quest "All this training Lily has made me tired"?
Can you not progress further than this quest? I just did a quick playthrough and it worked for me.
What should happened is after you study with Bront, you train Lily's love and submission to 5 and then sleep for the night.
Lily will then have a scene where she's thinking about studying more.
Thank you for replying when you could be busy or tired and where was i supposed to learn to study with bront? i tried talking with them now but it does nothing my guy is like still why do i even try. was that a typo? but yea it doesn't give me the scene for Lily is it cause i went aggressive/dominant on her? should delete all saves and start over?
Basically, what should happen is.
1. You meet the mayor, to discuss saving Lily.
2. Then sleep and then tell Lily the next day you'll train her.
3. After she agrees, you try training her/helping her study but you aren't smart enough.
4. You go find Bront during the morning to help you study.
5. Then you should go back and train/help Lily study again
6. You then train Lily's love and submission to level 5 and then sleep.
It should work since there's really no room for change here, but if somethings gone wrong, maybe make a new save file and see.