I'm playing a thief, and one of the first things I did was to get myself arrested in Whiterun so I could break out of prison. Fourteen levels later, I get back around to doing the "In my time of need" quest (the one with Saadia and Kematu). I talked to the Alik'r prisoner, he told me to pay his fine, but whenever I click on a guard I just get the "Wait... I know you" line. No dialogue options, no way to pay his fine, no way to clear my bounty, nothing. Just "Wait... I know you" every time I click on a guard. Even repeat-clicking won't do anything but make them say the line.

I considered trying to get myself arrested again, but figured I'd come here first in case it's a known bug with a fix (couldn't find the exact problem with google). Didn't want to make a bad problem worse in case arresting didn't work... Any ideas?

Do you have any bounty in Whiterun? Even a small one would still bring up a "Wait... I know you" line, though it definitely sounds like this guard is bugged. Try talking to a guard outside of the dungeon not related to this specific quest.

Yep, tried that too. Ran around Whiterun double-tagging random guards to no effect.

I do have a bounty in Whiterun (25 I think - whatever you get for pickpocketing a guard), but can't clear it due to this bug. Or glitch, or whatever it's officially called...