At 9 Hearts, you will experience the first part of the Courtship Event that ends in your acquisition of an Engagement Ring. I posted Mana's Request at 9 Hearts previously. Once you have experienced that event, you need to return to the Bulletin Board where you will find a new Request: A Challenge from Douglas!
The following documents Douglas' Request Event:
The Event is mainly captured in short video clips to include the original music, as there are at least three different musical themes that occur in the course of Douglas' Event.