
Since Damien went out with Angela who also dated William at some point, who also dated Damien... XD
I don't know I just find that quite an amusing idea.
That aside as far as my wants go:
Roommates: Donald and Luke (and then we can go prank Virginia for fun.

I can't really choose a female romance option, as I haven't seen many who intrigued me, aside from Pastel who is not available. Minnie (Ellen and Virginia too) is more of a friend-type, and other female characters weren't really given enough depth for my interest.
It'll be interesting to see how Damien seduces a Wolf Hall non-wildseed student (Somehow I don't think his Horse Hall flirts are going to work this time!)
It'd be nice to get a better grasp of his personality too. All I trust about him is the fact that I can never trust anything about him! (and that he's sadistic and dangerous... why do I adore him so much!?)
Throw William in and it will be the best romance ever. EVER.
Just a thought, but far, far (farfarfarfarfar...) far away in the future, if the Magical Diary games made enough money to create a game that allowed you to play in one of all six houses, from freshman to senior, it would be a lot of fun.
Too bad that's highly unlikely to happen.