@Solitude  
I usually try to be^^

@Celestia’s Servant  
Yeah? News to me. I’ve only known you to be a friendly sort.

@Solitude  
Sometimes, I am. Mostly I’m just a mean bastard XD (At least according to other comments I got, especially on my blog.)

@McClaw  
Yes, well, it’s the third one here on Derpibooru. The first one was back on Ponibooru.
 
@Celestia’s Servant  
You’re too kind.
 
Miss Cheerilee, first permit me to say that you are the most adorably squishiest pony. For my question: are there any classes you find difficult or bothersome to teach?

@Solitude  
Three times? This is “round for” with her!

@Solitude  
Okay, just post your question and I’ll see. I’m feeling generous today.

Three times Cheerilee goes up, three times I miss her. Must be divine intervention or something.

Odd, normally these go right up til the last minute. I hope there’s enough content in here.  
Also remember to use my third one, since I had my first two snagged. xD

What’s your full, honest opinion on Diamond Tiara? Don’t be afraid to hold back. We won’t blame you, Miss Cheerilee.

As Cloud Swarmer’s former teacher, how would you say he’s done since graduating (or maybe he didn’t?)?
 
@Gig, Master of Death  
(Cheerilee, if you’ll accept any help dealing with this guy, I’m your griffin. Not that you’ll likely need the help, or lack it if you do need it.)

Educational hugs?

@Vitruvius  
And to piggyback off of his question, has there ever been a desire to teach in secondary education or even in higher education?

who would you say is the worst student you’ve ever had?

Do you know you are both smart and adorable? Cuse you are. Hugs?

Alright this time, I’ll have an original one for sure!
 
Have you ever considered student exchange programs? I know it might be tough to get rural parents to go for such a thing, but I think it’d be quite beneficial for them to experience differing methods as well as study cultures. That li’l guy with the fez seems pretty well-read, he could be a good candidate for such an experience. I know that Trottingham had two successful test runs with Saddle Arabia recently.

What kind of book do you read?

If you ever get sick, who usually fills in for you?

Are you planning on taking your class to a field trip soon?

Ugh… How the hell do you put up with those little snot nosed brats all day? Maybe I should be the teacher. I’ll give them lessons from the school of hard knocks. Heh heh heh…

Do you still talk with Twilight much since she became a princess?

What do you like to do when you’re not teaching or grading?

Are there any other teachers in Ponyville? If not, do you have to teach all grade levels?

Do you expect there to be any changes to your job now that Twilight has a palace right there in Ponyville?

Pezuña was a no-show at his trial, having skipped out on bail! I don’t know if he’ll risk showing his muzzle in Ponyville, but I would advise being on the lookout.