In session 5 after a terrifying battle with Kiel Raulhausen, Darek suffered from some immense trauma over his first human kill. Lady Pridwyn gave him a calming drinking to ease his panic. However this didn't stop Canna from worrying about her brother. She went out of her way to find some sweet potatoes and payed the barmaid at the Cask'n Flagon to show her how to make mashed Sweet Potatoes, one of Darek's favorite foods his mother use to make. The siblings bond and hug, Darek stating that he loved her and that he doesn't regret following her over the wall for a second. Not long after Darek reassures Dahlia that he's alright and offers to share his sweet potatoes with her. Both moments were incredibly sweet and adorable.
After returning from their defeat against Lord Errol and Xellia, Darek checks in with each of his party members to see how they're coping. When he finally confronts Dahlia while forcing down some beer (which he hates) for some liquid courage, he expresses his regret he couldn't protect her in battle, choking up as he apologizes. Dahlia reassures him that there was nothing he could have done and he doesn't need to apologize, the two of them agreeing that from now on they'll both strive to protect the group, including each other. Shortly thereafter, Dahlia also confesses that she has been harboring feelings for Darek. Y: Ruler of Time committed to Darek's drunken breakdown to such an extent that he made his nose run. Pure gold.