What I think we should try to do is get our characters together in a more personal group, where they'd have to interact with each other instead of sort of just hanging out by themselves. The party thing isn't a bad idea per say, but it would be rather easy for us not to talk to each other because we simply don't have to. But if the group was, to say, all thrown into prison, we'd have to coordinate and talk to each other and figure something out. Maybe even get to know each other one-on-one. Or in a less extreme way, have our characters do some chores together for a chance to interact with someone and open up conversations.

I wouldn't call Malakaus shy, but if he doesn't have to talk to someone, he probably won't. If he can work by himself, he likely will. Put pair him up with someone, and he'll might as well strike up a conversation while working.