Below is a walkthrough of Ryker’s Romance Stories in Rune Factory 5.
Chronic Sleeper
Requirements: Friendship Level 2
Location: Great Tree Plaza
Objective: See what Ryker is up to
Stop by the Great Tree Plaza for a dialog event with Ryker, Hina, Julian and Simone. After a couple of days pass, you’ll get another event with Ryker on the beach south of Great Tree Plaza involving Yuki and Ryker sometime after 7pm. When it concludes, wait for the next day, then head to one of the houses south of the Great Tree Plaza in the morning around 8am to find Ryker chilling on the ground near a fence for another dialog event. Wait until the next day then head to Studio Palmo. This will trigger a dialog event with Yuki and Simone. This will complete the event.