I think you have to go out on a date with Jake. For that you need to complete quarrel with her friend and cease to be a nerd tasks.
Quarrel with Murano is several steps: first Murano has to decide that she is better off without Anabel - this happens at school, but she actually tells Anabel she's leaving at the Library. Then, at home Anabel decides that she also doesn't need Murano. Next day in class, talk to Jake or Bobby about hitting on Anabel. This will trigger a scene where they come chat up Anabel while Murano is missing. When that's done, talk to Murano and tell her she's Anabel's ugly friend. She'll get mad and leave. Then visit Anabel in the library again, and Anabel will decide to end it with Murano, completing the task.
Cease to be a nerd just involves MC angel whispering to Anabel all the time about lowering study or doing something else instead of study. Once it's below 60, talk to Jake at school during break and get him to ask Anabel out. Might have to do it a few times. Then watch the map after school to see when the even in the park starts.