The video games listed in the poll... half of them I've never heard of, the other half I've never played. I am, though, reminded of another comic's arc where someone (while clearly dreaming) found themselves in TES:Oblivion, along with another major character. After a strip or two of 'this game isn't even multiplayer!', they split up. I can easily envision Winslow and May in a similar situation in Skyrim. Winslow, after his initial disbelief, would become resigned to making the best of the situation and start out following the main quest. May... is May. She'd be off like a shot, and by the time Winslow's meeting the Jarl for the first time, she's already being chased by angry NPCs and livestock from three or four holdings, and accidentally burned down Winslow's next quest location on the way.