I don't think people have a right to lie to other people. I also can't understand why you would regret breaking up with someone so truth-averse and horrible.
How does this help me become more rational?
That's ridiculous. So mild pains don't count if they're done to many different people?
Let's give a more obvious example. It's better to kill one person than to amputate the right hands of 5000 people, because the total pain will be less.
Scaling down, we can say that it's better to amputate the right hands of 50,000 people than to torture one person to death, because the total pain will be less.
Keep repeating this in your head(see how consistent it feels, how it makes sense).
Now just extrapolate to the instance that it's better to have 3^^^3 people have dust specks in their eyes than to torture one person to death because the total pain will be less. The hair-ripping argument isn't good enough because pain.[ (people on earth) (pain from hair rip) ] < pain.[(people in New York) (pain of being nuked) ]. The math doesn't add up in your straw man example, unlike with the actual example given.
As a side note, you are also appealing to consequences.
The point is that to an AI, we are but massive, stupid beings who are attempting to teach them minor symbols with massive overuse of resources(that few lines of code to define "rock" could be used by a sufficiently powerful UFAI to, say, manufacture nukes).
I'm there with one other person. Look to the lesswrong Singapore google group for any future updates.
Finally, a Singapore meetup! Will definitely be there.
For me, the problem with this is that if I'm speaking to an autistic person(and a very large number of LWers identify themselves as on the autistic spectrum), they tend to use literal meanings very often. In fact, some of them(including me) get offended or confused when they say something literal and it is interpreted as sarcastic or subtext.
Suppose I am speaking to an autistic person, and he says, "I am 87% confident that X is true." The issue with this statement is that a lot of people use this sort of statement in a metaphorical sense(ie. they just pull the number out of their butt to make it oddly specific and get a cheap laugh) but an autistic or rationality-trained person may literally mean that they are 87% sure it is true, especially if they are good at measuring their own confidence levels. In this case, the usual situation- the number being picked randomly - is false.
There are also, however, a large number of statements that are almost always meant sarcastically or in a non-literal way. The statement "I, for one, welcome our new alien overlords" is almost always sarcastic as it is 1) invoking a well-known meme which is intended to be used in this manner and 2) it is extremely unlikely that the person I am speaking to is actually someone who wants aliens to take over the world. These statements are, for want of a better word, "cached non-literal statements"(as in, it is an automatic thought that these statements are not literal), or CNLS for short.
It might be useful to append the guideline "All statements have a probability of being literal that is worth considering, except in the case of CNLSes. This probability is adjusted up if the person you are speaking to is known for being extremely literal and adjusted down if they are known for using figurative speech(although that last sentence should be fairly obvious, I throw it in for the sake of completeness)" to your thesis.
This actually got me thinking if there is a methodical, objective and accurate way to find out if someone's statement is literal or not, perhaps by measuring their posture, tone of voice. The only difficulty is to try to weasel some quantifiable data out of context. If it can be done, that would be a great resource to people who have trouble understanding the non-literal meanings of statements everywhere.
No problem, and I hope this post taught you how to work better and learn better. If you have problems with procrastination, you can try programs like Beeminder, or simply have a friend act as a watcher to ensure you get your work(or your three new things) done for the day, week or month.