I haven an enormous inferiority complex when it comes to using the English language. You can thank my mother for that. Mom is not merely the sort of person who got a perfect 800 on the verbal portion of the SAT and can learn the basic grammar and vocabulary of nearly any language within 3 days--she is that person. So while I know it's considered poor taste to blame one's failings on one's parents, my mother drove me nuts. As kids, my brother and I were continually subjected to snap vocabulary quizzes, corrected when our pronunciation sounded deficient or sloppy, and even though I didn't know what grammatical rules were--I couldn't recite them on demand, for example--I developed a permanent feel for them. Reading helped--my whole family is filled with compulsive readers (including myself). Hebrew school was a little complicated at first because when the teachers referred to The Bible I thought they were talking about the Random House Unabridged Dictionary in our living room. Most seven year olds thought the thesaurus was an obscure sort of dinosaur, but to us it was the other dictionary. The best present my parents ever gave me was the Random House Encyclopedia for my eighth birthday. Absorbing that was a religious experience for me, and to this day, I haven't found the classroom able to compete with it.
In hindsight, Mom clearly did me a favor although I had to turn to writing and teaching English in my early twenties to realize this. More importantly, in the 20 or so years since then I have had the chance to read, edit, and correct the work of innumerable others who clearly did not have my Mom helping them out in their formative years. I see the same mistakes both from students and professionals who, frankly, should know better. Spelling errors, mistaken contractions, and grammatical gaffes are, of course, part of the life of writing for any purpose, but the fact that I see the same problems in both students and their teachers has me worried.
At any rate, this is meant as friendly advice and while I admit my perfectionism is probably genetic, I think perfect writing skills are something worth aspiring to. (As a final note I would like simply to point out that any mistakes in this post are entirely my own fault, not that of my mother.)
Here we go . . .
How many times have you heard a friend tell you that “I could give a shit,” or “I could care less.” The correct phrase is “I could not give a shit,” or “I could not care less,” and it always has been. In case you think I’m being an elitist bastard, think about it logically for a moment. If you could care less it means you actually care. If nothing else, it means you care to a level that is not zero (since negative caring is not logically possible). If you could not care less, then your level of caring is at zero, which is an absolute point of non-caring. In other words, telling people that you could care less means you give a shit and vice versa. If you really and truly don’t care, say it correctly.
Using “It’s” as a possessive pronoun is just plain wrong. The reason is simple: “it’s” is the contracted form of “it is.” “It’s raining out.” “It’s too hot in here.” “It’s time to load the guns because those zombies aren't going to kill themselves.” “Its”, written without the apostrophe, really is a possessive pronoun. “The dog wagged its tail.” “The car lost its muffler on the highway.” “Hey, Fred, the volcano is flipping its lid.” Same sound, two different meanings and respective spellings (that's called a homonym for you etymology junkies). Think about what you actually mean to say before writing it down.
There vs. Their vs. They’re. This one makes me nuts, but it's easily corrected if you just keep the context of the statement the word appears with in mind. Observe:
There means "there" as in "That, over there" or "Not here, but there" or "There you go again, you silly Democrat."
Their is a possessive pronoun for a group which modifies a noun : "They took their ball and went home." "What is ours is not theirs." "They stumbled drunkenly as they looked for their house in the dark."
They're is a contraction for the words "they are." As in: "They're crazy." "They're rich as Nazis." "They voted for Bush twice, and now they're voting for McCain." And so on.
More/Less vs. Many/Few. This one takes a bit of explanation, but at its root is the difference between an amount and a number. An amount is a portion, like a cup of sugar or a ton of grain, or something of that nature. A number is a group of individual objects, like one, or ten, or a gazillion. So when writing this you should consider the essence of what's being described.
On that note, "More" and "Less" refer to amounts, while "many" and "few" refer to numbers. So I can have more sugar or less grain. Or, I can see many stars with a good telescope, or see that I have ten fewer spoons in the drawer at home.
Two, Too, and To. In the simplest terms I can imagine:
Two is the number, two.
Too is an adverb that means "also," "as well as," "in addition to," and such like.
To is a preposition that denotes motion towards a goal: "I went to put my paycheck in the bank," or "The gangsters went to rob the bank," or "They went to repossess the house but I burned it down instead," or something similar.
And there you have it: the problem words I see the most often and the answers. Use them well, and often. Mom will thank you (and so will I).

Oh, my goodness, I was SO with you, cheering along paragraph by paragraph, laughing as I recognized your mother (obviously my mother's twin sister). Right until the very end, where every single "to" example you offer is not a preposition at all, but part of the infinitive form of a verb!
"I went TO THE BANK (prepositional phrase) TO PUT (infinitive) my check in." Or "The robbers went TO THE BANK (prepositional phrase) TO ROB (infinitive) it." Or "They went TO THE HOUSE (prepositional phrase) TO REPOSSESS (infinitive) it..."
Tsk, tsk.
Posted by: Betsy | March 29, 2009 at 12:01 PM
Ach! I weep! And thank you.
Posted by: Jonathan Frater | March 30, 2009 at 11:16 AM