It’s a beautiful Monday. Everyone is out and about for their typical day. The kids are in school for another long five days. Life is great, especially for those that are teachers.

A positive-minded pony named Cheerilee is a well-known figure within the small town of Ponyville. She’s a teacher at the local school where she teaches young ponies a variety of subjects. Everyone loves her and her optimistic personality. She’s touched the lives of many ponies alike, but never had she thought of impacting the life of a lone human in Equestria.

Cheerilee had one day encountered this human at the food market. She had heard of him before, but had never actually seen him in person. His name was Anon, he was the only human residing in Equestria. As the two were looking at fruit, they both bumped into each other sparking up a conversation which eventually grew into a good friendship.

It’s been about a year since that day and now both Cheerilee and Anon are great friends. Some ponies even started to picture them being a couple. Much to Anon’s dismay however, Cheerilee would quickly brush off those rumors if brought up. Overtime Anon had started developing feelings for her. What Cheerilee had that other ponies didn’t was the fact that she happily accepted Anon as a friend for who he is. Many other ponies were intimidated by the bipedal figure and were typically hesitant to interact with him.

Cheerilee was obviously unaware of Anon’s feelings, but he didn’t mind for now. He was planning on waiting until Hearts & Hooves Day to give it a shot, but that was another two months away, he had plenty of time.

With it being a Monday, Anon knew Cheerilee would be busy educating the young ponies. He didn’t even realize she was a teacher until about 2 months after he met her. He respected her for being able to put up with children. Even though Cheerilee always claims she loves teaching, Anon knew her well enough to see that some days she doesn’t even want to bother with teaching.

Typically once Cheerilee would finish up for the day, her and Anon would get together and do a variety of activities. However today Anon was gonna surprise her by showing up to the school itself.

It was only 1:00pm according to the position of the sun, Anon decided it would be nice to gift her something. He thought flowers would suffice and maybe a few cupcakes. She could have a rough day for all he knew, so an act of kindness would hopefully turn it around just in case.

Anon made his first stop at Sugarcube Corner to grab some cupcakes. Typically a frantic pink pony would be there ready to tackle him down and start rambling nonsense at the speed of those narrators at the end of commercials, but this time was not the case. Instead he came across one of the actual owners of the joint, Mrs. Cake. In his view, she was a smoking hot MILF. Since she was married however, he accepted he wouldn’t get a shot with her.

“Oh uhhh hello Mr. Anonymous! How may I help you today”?

“Please, just call me Anon. I’m here for a few treats...it's for a friend of mine. I’ll take two chocolate cupcakes if that’s alright” Anon said shuffling his hand through his pocket.

“Two chocolate cupcakes you say? Alrighty dear, coming right up”.

As she went into the back to gather the materials, Anon sat himself down at a table nearby and waited patiently. Within a minute or two, Mrs. Cake had presented herself once more with the treats Anon had requested.

“Okay, that will be 4 bits Anon”.

“Only 4 bits?” the human asked raising his eyebrows.

“I’m giving you a discount for being a regular customer and always trusting us for your bakery needs. Think of it as a gift,” Mrs. Cake said giggling.

“Oh uhh, thank you Mrs. Cake, that means a lot”.

“It’s my pleasure, dear. Now you go have fun with your friend,” she said with a smirk on her face.

“Will do”.

With that, Anon departed Sugarcube Corner. He can finally say that he managed to visit Sugarcube Corner without being pounced by Pinkie Pie. He honestly wondered where she was at that point but quickly brushed the thought off. His next stop was to visit Roseluck and buy some flowers.

As Anon made his way to the marketplace in town, he saw out of the corner of his eye a familiar pink figure. He immediately knew exactly what it was, and it was coming straight for him.

“No..NO...NONO..NOOOOO PLEASE NOO!” he screamed internally as the pink pony sprinted towards him. He braced for impact.

“NONNYYYYYYYYY!!!!!” was all Anon heard before he was practically body slammed by Pinkie. As much as he loved the pink pony, he never really enjoyed how hyperactive she was to him for the most part. Nonetheless they were still friends.

“Nonny hey! Whatchu doing with those very scrumptious looking cupcakes” she said clearly hoping she can snag a piece.

“Okay first, can you get off me? I can hardly breathe”!

“Whoops, sorry!” she said giggling.

“First off, these cupcakes are a gift for a friend. An act of kindness. To answer the other question you probably have in your head, no these cakes aren’t for you unfortunately, sorry”.

“Awwwww okie dokie lokie. Who’s it for then”?

“If you happen to know who Cheerilee is, it’s for her. I figured she might be having a rough day with all the kids so I thought ‘why not?’”.

“Ooooooooooo okay! Well….I’ll let you get to that because I just remembered I gotta hurry up to Twilight’s castle for a little meeting. Talk to ya later Nonny!” she said as she suddenly dashed off like a bullet.

“Well that went better than expected,” Anon said to himself.

Continuing through the marketplace, he set his eyes on his target. He spotted the flower shop where Roseluck works. Roseluck to Anon was a very sweet pony. He always came to her for all the flowers he needed. Roseluck never disappointed him with the stuff she had.

Upon entering the shop, he looked around for Roseluck and noticed she was busy watering some plants. He decided to ring the little bell near the door to get her attention.

“Oh? A customer? Just a second I’ll be right there!” she said as she stopped watering and went to put the watering pot in her tool room. Once she finished, she made her way to her guest.

“Oh hi Anon! What brings you here”?

“I’m here to grab a flower bouquet. What do you have in stock today”?

“Oh I got a variety of things. I got a few roses, some bluebonnets, daisies, lavenders and plenty more. See anything you like”?

“Hmmmm, I’m interested in these lavenders right here. How much are you wanting?” Anon asked as he smelled the flowers.

“I’ll offer 8 bits for this pair right here. Sound good for you”?

“Yeah, that works just fine. Here you go,” Anon said dropping the 8 bits on the counter.

“Alright thanks Anon. Might I ask what you’re using them for”?

“Hmmmmm? Oh they’re a gift for my friend. You know who Cheerilee is right? It’s gonna be for her”.

“Awww that’s sweet of you. I think she’ll love those flowers, she always loves the flowers I have in stock. Hey be sure to tell her I said hi okay”?

“Haha, alright I’ll be sure to do that,” Anon said looking outside and studying the position of the sun to get the time. He noted it was 2:00pm at least, so he had to get going. Class would wrap up at 2:30pm.

“Anyways, I gotta get going. Thanks a lot Roseluck, I’ll see you later”!

“No problem, you take care”!

With the presents acquired for the receiver, Anon started making his way to the local school Cheerilee worked at. He would probably get there in about 15 or 20 minutes depending on his walking pace. Knowing class wouldn’t be over by the time he got there, he wondered how he was gonna surprise Cheerilee without one of the little ponies possibly giving him away. He then decided hiding in a bush would suffice.

“Oh Cheerilee won’t be expecting this!” Anon said with a chuckle.

Author's Note

I've scrapped probably almost 15 ideas for this story and finally settled on something like this. I will gladly accept any criticism for this story.

Anyways, next chapter is when Cheerilee officially comes into play.