I'd have to say Douglas also, because he's always trying to get Jen to come fix his computer. As though there is nothing insinuating about the event. "My computer isn't working." Jen, "Is the computer plugged in?" It's just hilarious with all the dialog. He unplugs his computer just to get her into the same room lol.
I must say Douglas takes the cake between his apathetic rants to his outrageous breakup fight the man is just a funny boss. May he never have police come looking for him over pension funds.