Additional contributions by MixMassBasher.

Dear Princess Cadance,

Worst advice ever. A picnic to woo Starlight on our one-on-one date didn't work at all!

She kept teleporting back to work in the middle of it!

Yours truly,
The Horny and Bewildered Trixie

Dear Trixie,

Guess Starlight must be into stallions, then. Try dyeing your mane red and your coat orange and wear a blue coat and spectacles.

Love,
Princess Cadance

Dear Princess Cadance,

Why did Trixie just demand message me to send her my wardrobe?

Your Confused Royal Crystaller,
Sunburst

Dear Sunburst,

Oh, she's trying some crossdressing because I made her think Starlight has a thing for nerds.

Sincerely,
Princess Cadance

Dear Princess Cadance,

She is into nerds.

Namely, me.

Sincerely,
Sunburst

Dear Starlight Glimmer,

Three strikes and you're out.

This is the third time something bad occurred while you were in charge of the school!

I will never let you be headmistress of my school ever again!

Signed,
Headmistress Twilight Sparkle

Dear Headmistress Twilight Sparkle,

I don't know about that. Most viewers already know that Starlight ends up being in charge of the school by the end of the show.

Guess that makes you the biggest idiot to put her in charge a fourth time.

Your bouncing employee,
Pinkie Pie

Dear Stupid Pie,

Shut the fuck up! Nopony asked you!

Your irritated boss,
Headmistress Twilight Sparkle

Dear Fluttershy,

I am in need of your assistance. I would like you to get a cockatrice and stone my stallionfriend.

Signed,
Maud

Dear Fluttershy,

Please don't.

Even if she managed to only make it to the portion of my body that she wants to keep hard forever, I am afraid that it would make urinating and ejaculating... Complicated.

A technically terrified stallion,
Mudbriar

Dear Mum and Dad,

Guess what new pet I got!

Your daughter,
Silverstream

Dear Headmistress Twilight,

We like to file a complaint on your supposed best teacher in your school; Professor Fluttershy. Who in the right mind thought it was safe for our daughter to tame such a dangerous animal!

Signed,
Sky Beak and Ocean Flow

Dear Silverstream’s parents,

Perhaps you underestimate the true bonds between tamer and creature. I wouldn’t be surprised if your daughter would be able to biomerge with Edith down the line.

Your expert beast tamer,
Professor Fluttershy

Dear Starlight,

Say, nice bracelet.

Can you make one that goes off when I'm horny?

Sincerely,
Headmistress Twilight

Dear Headmistress Twilight,

So... You want me to make you a bracelet that never stops vibrating?

No.

Sincerely,
Counselor Starlight