For the optional task 'Pride and Prejudice'
....Just how exactly am I supposed to tackle it? Beverly beats me every time and I'm not exactly sure how I'm supposed to win.
The short answer is to talk to Bianca in the dungeon. She'll tell you what to do.
The long answer depends on which step you're on. If Bianca isn't there yet, you have to continue the story until she asks you to meet you there. Assuming you're stuck on the first step, make sure the challenge is active when you talk to her.