Same here. I have never really been a fan of the pairings. Kishi doesn't seem to focus on them all that much either so I never really given it much thought myself.
But sure, I could see Kakashi with Anko. Their personalities are compatable and as the OP said they do have that certain darkness in their pasts.
Anko, the lady who were once disciple of orochimaru and now who is left behind over 50 chapters i guess, are you talking about her, let me think again.........nah, she has became bit more than just a fodder, i don't think kakashi would give her any looks at all, i guess ibiki the interrogation guy(don't know whether he is still alive or not) will much suit to her