I just wish he'd take some remedial language courses or something.
Your and You're
Understand the proper usage of the word you need. The best way to do that is to sound it out. There is a replacement test that will tell you for certain which word will fit. Read your sentence with "you are" in place of the "your/you're," intended. If it makes sense, then "you're" would be right. If not, then "your" would fit. You could also replace "your" with "my" in the sentence. If it fits, then use "your."
To, Two and Too
People seldom mix “two” up with the other two; it obviously belongs with words that also begin with TW, like “twice” and “twenty” that involve the number 2. But the other two are confused all the time. Just remember that the only meanings of “too” are “also” (“I want some ice cream too.”) and “in excess” (“Your walkman is playing too loudly.”). Note that extra O. It should remind you that this word has to do with adding more on to something. “To” is the proper spelling for all the other uses.
Their, There and They're
Their is a possessive pronoun. It always describes a noun.
Note the spelling of their. It comes from the word they, so the e comes before the i.
There is an adverb meaning "that location." It is sometimes used with the verb to be as an idiom. It is spelled like here which means "this location."
They're is a contraction of they are. Note the spelling: The a from are is replaced by an apostrophe.
Examples: Their dog has fleas. (possessive of they)
I put the collar right there. (that location)
There are five prime numbers less than ten.
(with to be)
They're 1, 2, 3, 5, and 7. (contraction of they are)