This one’s easy. Your means it belongs to you. Your pen means the pen belongs to you.
You’re is a contraction combining the words you and are. So you’re means you are.
So we can never accurately say “Your cute” unless that person has something called a cute. We would want to say, “You’re cute,” which translates into “You are cute.”
If you can say ,“You are (whatever),” then feel free to combine you and are into you’re. Otherwise, if you can’t say “you are….” then you probably want your.
You have my permission to make every legal effort to change every sign or advertisement that gets this wrong.
They’re is a contraction joining they and are. The apostrophe has nothing to do with a possessive, but simply takes the place of the missing “a” when you combine the two words (such as didn’t).
So if you can write they are for a situation, then you can write they’re instead.
Their means belonging to them, whoever they are. Their friends, their boots, their thoughts. We can never say they are boots unless you are calling those people boots. If they own boots, we would say their boots.
There used to be spelled correctly almost all of the time. Now it’s in the same danger as those other two words that sound like it. There indicates a direction: “I put it over there, next to the couch.” But you already knew that.
We live in an age of exaggeration, and these two wonderful words have been two of the victims. Let’s do what we can to bring a measure of reason and exactness to them.
Literally means actually. Not like, not similar to, not as if, but actually. If something literally happened, then it really did happen in space and time.
Figuratively means that something was like something else, that it was “as if” something were like something else, but in actuality, wasn’t. We use word to create a comparison.
If something literally cost you an arm and a leg, that is both criminal and painful. If you say that it did, we should all know that you are speaking figuratively (we hope).
If something literally blew you away, then you ended up, due to high winds or an explosion of some sort, in a difference place from where you began.
If you were literally broke, that means that you have no money. Not a sou. Not a dime. Not a penny.
What we need to do is gently and slowly bring back the word figuratively into our speech, or at least into our written expressions. Or better still, let’s simply drop the word literally from our speech and writing altogether, because most of the time, we mean figuratively anyway!