As a female Slytherin I'm having a lot of issues with quest 20, Bracelet. Looking at the walkthrough, the requirements are "be less than friends with Draco" as well as having done his date, quest 10, which requires that you "be best friends with Draco"... what? As backwards as it sounds, I regressed our relationship to the point of "Like" and this still never triggered. Even when I kept the relationship the same, it just progressed to all of his sabotage quests instead.
Might be worth mentioning that I allowed gay content at the start of the game? I didn't really think it would affect my character...