One reason I find social interactions confusing is that there are so many questions that have secret, pre-set correct answers. And there's no rule-book, so you've just got to figure this out on your own.
Some questions only have one correct answer. For instance, if your mom says, "Cindy, would you like to help wash these dishes?", there's only one acceptable answer to this. You might think that you should tell the truth, since that's what your mom always taught you to do, but it turns out that you're not supposed to tell the truth in response to this particular question. [Well, you can tell the truth if you would actually like to help with the dishes, but I always had to either lie or give offense.]
Another question that only has one acceptable answer is "Does that make me a horrible person?" Fortunately, most people only ask this question in contexts where the correct answer ("No") is also the honest answer. For instance, someone will say, "Last night after volunteering at an orphanage and helping twenty old ladies across the road and giving home-made afghans to everyone in the homeless shelter, I saw someone trying to hitch a ride by the side of the road, and I didn't pick him up because he looked crazy. Does that make me a horrible person?" This question makes you an annoying compliment-seeker and indirect boaster, but it does not make you a horrible person.
I don't think I've ever heard anyone preface with question with something that might actually call their horribleness into question. I guess that makes sense -- most people don't actually want honest feedback, so they won't ask questions that might elicit a debate about their character. For instance, I could say, "You know, one time I intentionally hit a pedestrian because he was walking so darn slowly in the crosswalk. Does that make me a horrible person?" But I don't really want to know if you think this makes me horrible.
Some questions allow more of a range of responses, but there clearly are still correct and incorrect answers, the correctness and incorrectness of which are independent of the truth thereof. For instance, guys often like to ask me what I like to do for fun. I really should be prepared for this question by now, but it still always catches me off-guard and makes me feel like I was suddenly given a pop quiz for a class I didn't even know I'd signed up for. And, unsurprisingly, I often end up failing.
"What do you like in your spare time?" one guy asked.
"Oh, I like reading and watching TV and just hanging out with my friends and family," I replied.
"No, I meant things that are actually fun. What do you like doing that's fun to do?" he responded.
He was an annoying guy anyway, so at this point I gave up on being polite and started being difficult instead. "Oh, I don't actually like doing fun things," I told him. "I just enjoy boredom."
"You've got to like something fun," he said. "Don't you enjoy hiking or skiing or jogging or anything like that?"
I don't mind hiking, although I hate the others, but I was too annoyed to concede even that much, so I told him I didn't like anything like this.
"Oh I know what you like doing -- you like going on dates with nice guys like me."
This got the response it deserved. Of course, this guy was obtuse enough that he probably thought my withering look was meant to be flirtatious.
"And you like bowling and going to amusement parks," he informed me.
"I hate amusement parks," I told him.
"No, you must like amusement parks. Everyone does."
"I don't," I told him. "I've got some bad memories at amusement parks." This was actually true -- I'd had some bad high school band trips to Disneyland where my feet hurt so badly that I just wanted to die, but instead I had to keep hobbling around all day pretending to have fun. But my date was unwilling to accept this answer, and instead he spent ten more minutes trying to convince me that I really do like amusement parks.
Another guy took a somewhat more tactful approach -- in response to my list of apparently boring hobbies, he said, "Nothing active? I think you should go outside more."
He then asked if I tried skiing or snowboard. When I told him no, he said, "Oh, you must go skiing. I must teach you skiing this winter." This guy has a thick Russian accent, so just imagine an 80s movie KGB agent trying to force someone to go skiing. It was pretty much like that. Good times.
I realized recently that part of my problem in social situations is that I value honesty and precision very highly, so I always try to come up the most honest, accurate answer possible, and only then do I use my social filter to figure out if this is also a socially acceptable answer. But this is an inefficient approach in social situations, since there's often little overlap between accuracy and social acceptability. I'd probably be much better at small talk if I could first think of socially acceptable answers, and only then subject them to the honesty filter, without worrying so much about coming up with the most precise, accurate answer. I'm not sure I can do this, though. Does that make me a horrible person?