Considering the amount of hours that can be poured into Elder Scrolls: Oblivion, players have more than likely come across a slew of awkward, oddly-timed conversations with the NPC inhabitants of Cyrodiil. It turns out that there is a distinct reason as to why this is the case.
In a behind-the-scenes interview with Bathesda Games Studios' Audio Director, Mark Lampert, it was revealed that the Elder Scrolls: Oblivion scripts for the voice actors had their lines listed in alphabetical order.
In the interview, Lampert implies that the alphabetical ordering of the lines was simply overlooked:
“There's also a picture I have somewhere, like a little behind-the-scenes making of sort of thing, and it's a shot of a script which, I'd probably just come from Kinkos, like three in the morning, to print and put into binders and all this kind of thing. And we didn't have a good way to - at the time, to sort by, ‘These lines go good with this quest; these lines go with this quest.’ But in that picture with that script, if you look at it closely, you'll notice the lines are all alphabetical sorted. It was one of those things I just didn't think of at the time while putting the scripts together.”
Lampert goes on to give credit to the voice acting talents that had to work with the redundant, alphabetical list of lines:
“It's a wonder they didn't lose their minds, because it starts off, it's all ‘A’ sentences and you know, wait until you get to the ‘Hello’s’ and the ‘Hi’s.’ There's pages like, ‘Hi, how are you?’ ‘Hi.’ ‘Hello.’ ‘Hello. ‘Hi.’ ‘How....’ ‘How….’ ‘How….’ You know, all while trying to maintain this character that they're supposed to fight.”
It does not sound like an unreasonable way to write a script for a game like Elder Scrolls: Oblivion, with its open world gameplay and option for players to entirely ignore any sort of linear, main storyline. On the other hand, it certainly sounds brutal for the voice actors and actresses, who would have to repeat the same words and phrases multiple times in slightly different ways.
At the very least, with this knowledge, it would be fair for players to give a little more credit and understanding to the awkwardness of the conversations in Elder Scrolls: Oblivion.