Each 'step' end in a quest, sometimes you have to progress other quest lines for that quest to trigger.Stuck at 25 Relationship with Rachel. How do I continue her story?
Alternatively, it could be a case that you've got too many things queued in your "wake up" slot (quests that trigger when you wake up). You can pop the next one off by leaving your bedroom and re-entering it in the morning, or by sleepinga day.