The Elder Scrolls V: Skyrim
Heimskr 'the Man'
Ages ago, I was in Honeyside and a couple of the followers started doing the "Oh I'm glad I ran into you..." routine. Normally, if there's no Nordic brute around to interrupt them, the conversation makes little sense. However on that occasion, Vekel the Man popped up in my house to deliver: "Hello ladies! Is there anything a big strong man can do for you on this fine day?" then wraps it up with his "Harpies, every one of them!" and buggers off out of my house again. Classic. I muse that he must have heard the conversation starting through the sewers and ran like ♥♥♥♥ to make it in time. :)

So I was in the Bathing Beauties Suite and two of the girls start that conversation. With perfect timing, Heimskr pops up do deliver the line. I'm not even accepting male customers so he must have come specifically to deliver the line. Ran all the way from Whiterun, he did. Interrupting his busy schedule of annoying the good people of the town. Unlike Vekel, I'm not quite sure quite how he heard the girls...