The Good, the Bad, and the Cheerilee (Low self-esteem)

>When you first arrived in Equestria you found yourself waking up in a trash heap in an alleyway in some sort of small city.
>Naturally when you stumbled out of the alleyway tiny horses ran screaming in all directions and you were quickly apprehended by guards.
>After getting prodded a few times by spears you were brought before the leader of the city.
>She introduced herself as Princess Celestia and asked what you were and how you came to be in the kingdom of Canterlot.
>None of the answers you were able to give explained how you got there and as such Princess Celestia declared that you were not to leave the castle.
>You understand why she was keeping a close eye on you.
>You were a heretofore unseen creature that mysteriously appeared smack dab in the center her kingdom.
>In a pile of stale garbage no less.
>After the necessary precautions and around the clock guard escort she began to warm up to you.
>You two even became somewhat of friends.
>Unfortunately you didn't like how everything was done for you in the castle.
>It was making you feel like less of a man so you explained to Princess Celestia that you wanted to find a place to stay on your own.
>She was saddened by that but she understood where you were coming from.
>She had insisted that you stay in Canterlot so that she could be nearby if you needed help with something but you felt it was too crowded and high speed there.
>There was also the little incident involving her sister, Princess Luna, that caused you to seek housing elsewhere.
>She was nice enough in the beginning but she got a bit (Read:very) sour when you jokingly called her moon-butt.
>Magic enhanced mega wedgies are no laughing matter and your poor tattered boxers are a silent testament to that.
>Celestia teased you for a week after that and Luna would always snort and look away when you tried to apologize.
>You decided that it would improve your relationship with Princess Luna if you just quietly parted ways.
>As in while she slept you took the first train to the farthest town in Equestria and hid.
>You vaguely remember hearing Celestia mention that there was a very rural town called Ponyville where her student lived.
>You think her name was Twilight Smeagol.
>Or was it Spergal? Sparkle?
>Yeah that was it.
>Princess Twilight Sparkle.
>Anyway, you remember that Twilight and her friends gave princess Luna a good whooping a while back so hopefully she wont be so eager to visit trying to find you.
>You knew well enough not to pry into such sensitive matters so the reason is still unknown to you.
>As soon as you got to Ponyville you followed Celestia's advice and made a beeline for where you were told Twilight lived.
>Princess Celestia sent word ahead of you and instructed Twilight to help you find a place to live.
>The two of you took a tour around Ponyville and after visiting several locations you were able to find a relatively costed cabin.
>Your pride took a nosedive when Twilight had to pony-up and cover the down payment on your cabin.
>You promised her that when you were able to get on your feet you would pay her back every bit spent and then some.
>She didn't understand what you meant about "back on your feet" but she appreciated the intent nonetheless.
>Since you only had the handful of bits Princess Celestia sent with you as a parting gift you felt the next order of business was to find steady employment.
>With the next objective laid clear you began your search.
>Thankfully with a convenient letter of introduction from Princess Celestia and a good word from Twilight you were able to quickly find a job.
>It was a decent sized shop named Rich's Barnyard Bargains.
>The owner was some pony named Filthy Rich.
>That was a really weird name but overall he seemed like a pretty good guy.
>Especially since he was willing to hire you on the spot.
>While working in retail was far from your favorite thing to do, you've gotten pretty good at it over the past few years.
>You were even able to come up with a few suggestions on how to improve the layout of the store and in doing so, you also managed to increase sales slightly.
>Mr. Rich was especially happy about that little detail.

>It has been about a month since Princess Celestia and Twilight Sparkle helped you settle down in Ponyville.
>Today Mr.Rich has asked you to watch the register because he had some business partners to go visit.
>Normally he has you maintaining the store while he handles the customers so you were up for the challenge.
>The morning went by fairly quickly with no noteworthy incidents.
>>However during the afternoon that all came crashing to a halt when she walked in.
>She had pink fur, a pale pink and white mane & tail and beautiful green eyes.
>Her eyes met yours for a moment and your breath seized in your chest.
>She slowly walks up to you with a half lidded gaze and then promptly faceplants into the counter.
>"Chalk."
>You shake yourself out of your daze and look down at the pony on your counter top.
"That looked like it hurt. Are you alright? Do you want me to get somebody?"
>She lets out a impressive yawn and looks up at you.
>"I need more chalk. Do you have any left in stock?"
>Getting a closer look you see that she has splotches of chalk dust matting her fur and she looks like she hasn't gotten a good nights sleep in weeks.
"Uh... yes, I'm certain we do. Give me one sec to grab some."
>Sparing a concerned glance at the sagging pony you quickly go to the other side of the shop and grab a pack of chalk.
"Here you go miss...?
>She peels her face off of the counter again and looks up at you.
>"Huh?"
"Your name miss?"
>"Cheerilee."
>Cheerilee?
>This poor pony looks anything but cheery right now.
"Alright, thank you. Here's your chalk miss Cheerilee."
>She digs two bits out of a bag hanging around her neck and drops them on the counter.
>"Ugh.. thank you."
>She takes the chalk off of the counter and slowly makes her way out the door.
>Just as she leaves Mr.Rich comes out of his office.
>"Who was that just now Anon?"
"Welcome back boss I didn't realize you were here. She said her name was Cheerilee I believe."
>"Ah yes, a nice enough pony but I feel bad for her."
"You feel bad?"
>"Absolutely my boy. She's the teacher over at the Ponyville Schoolhouse and it's running her ragged."
"Really? What's going on that's got her looking like she hasn't slept in weeks?"
>"She's been in some unfortunate mix-ups over the last year or so and that hit her self confidence pretty hard."
>"To add top it off she's responsible for watching the Cutie mark crusaders."
>You don't know what that is but you remember how you were as a kid and feel a pit of dread form in your gut.
"The cutie mark crusaders sir?
>"They're good kids really, they just destroy everything they come in contact with when they've got some idea or another."
"Oh ouch. That poor lady."
>"Indeed my boy, indeed."
>As Cheerilee drags herself home she thinks back on her trip to the store and the unusual creature that was working there.
>Had she been slightly more awake she may have even tried to make some small talk with him.
>He had asked if she was alright. It's been a while since anybody seemed to take any interest in her.
>Cheerilee shakes her head swiftly to clear her thoughts.
>"No you silly old girl, get your head together. No pony would want someone like you at this point in your life."
>"They didn't want you when you had braces and they sure don't want you after the last Hearts and hooves day."
>She leans against the side of a building and tries to fight back tears.
>After a few minutes and a sniffle she resumes her walk and heads home for the evening.

>It's finally your day off and you've been spending it the best way you know how.
>And that's by sitting in your armchair, wrapped in a blanket, and not doing a single constructive thing all day.
>Sure you'd love to go outside and pull the weeds from your front lawn or maybe fix that squeaky shutter but that can wait until later.
>Besides, it just started coming down out there and you don't want to get wet.
>The sun has set and you watch as the lamp pony runs down the street lighting the street lights.
>Poor guy is getting drenched out there.
>You squish back in your chair and snuggle deeper into the blanket.
>Oh well not your problem.
*GRROOOOWWWLLLL*
>Your stomach sounds off an angry protest at the distinct lack of food in it.
>Groaning you peel yourself out of your blanket burrito and shuffle your way into the kitchen.
>Searching through the cabinets and the fridge you discover that you put off food shopping too long and now you have to head into town.
>Welp, it looks like the rain is about to become your problem.
>Of course the stupid weather ponies would have to pick your only day off in the week to make it rain.

>Grabbing your coat off of the hook you head out the door into the rain.
>Of course you wouldn't have had forethought to buy an umbrella would you?
>Grumbling, you pull your collar up around your neck and hurry through the rain heading for the market.
>Hopefully not everybody has closed up for the night yet.
>Thankfully you manage to find a vendor still open.
>Conveniently he has a sheet set up over his stall blocking most of the rain.
>The pony looks surprised to see someone running about in the rain but is happy to make a few more bits either way.
>The vendor is a older pony with a greying white coat and a thick, bushy, white goatee.
>He's wearing a red and white striped apron, a tiny matching paper hat, and thick black glasses.
>He distinctly reminds you of Colonel Sanders from back home.
>What you wouldn't give for some buffalo wings right now.
>"Nasty weather we're having today eh?"
>You really aren't in the mood for small talk but you try to humor the fellow anyway.
"Ugh, you've got that right."
>The pony extends his foreleg in your direction.
>"The name's Sanders stranger. What's your name?"
>You shake his hoof while stifling a laugh.
"My name is Anon, good to meet you Colonel."
>"Colonel? No sir, not me. My folks always said I was too chicken to enlist in the guard."
>You try to cover your laughter by coughing into your shoulder but you don't quite nail it.
>Mr. Sanders looks up at you with a eyebrow raised.
>"You feeling okay Anon? You sound like you might be coming down with something."
"Uh... yeah, I'm fine just a little tickle in my throat."
>He continues to stare at you for a little while longer before shrugging and motioning towards his goods.
>"I'm sure you didn't come all the way here to chat with a old man like myself so lets get to the good stuff eh?"
>Your stomach once again growls in agreement.
>"Ah, I see exactly what it is you need my friend."
>Sanders points to a sack of potatoes.
>"These here 'tatoes are a steal at a mere six bits."
>You still aren't used to how ponies value their goods but you can recognize the smell of being ripped off anywhere.
"No way buddy. I wouldn't pay more than two bits for that sack. You've got to be kidding me."
>"Hmm... How 'bout five for the sack and I'll toss in a discount on this here appul pie for another three?"
"Not gonna happen. I don't care how hungry I am, no more than six for both.
>He adjusts his glasses and thinks for a moment.
>"Tell you what, since it's getting late I'll add in this here bag of secret 'tato spices for free."
"Secret potato spices?"
>"That is correct Mr. Anon. You just sprinkle these here secret Sander family spices on yer 'tatoes and they'll come out delicious guaranteed."
>Maybe now you'll finally be able to crack those eleven secret herbs and spices.
"So I get potatoes, a apple pie, and secret spices for eight bits? Tempting but I draw the line at seven."
>A smile lights up the old pony's face and he holds out a bag for you to drop the bits into.
>"Pleasure doing business with you Anon, Y'all come back now real soon okay?"
>Mr. Sanders places all of your food into a box and waves goodbye as you head back into the rain.
>The rain seems to have gotten stronger.
>You grimace as you head back through the darkened streets.
>The street by Sugarcube Corner seems to have flooded so you decide to cut through the park instead of trying to wade through the puddles.
>Partway through the park you come to a halt and almost drop your dinner.
>Sitting at a table a little ways in front of you is the pink pony from yesterday.
>Why is she out here during this storm?
>She seems to be slumped over the table with her head resting on one of her hooves.
>Forgetting about getting home you quickly rush over to the table to check on her.
"Hey you! The one from yesterday!"
>She turns in your direction and then rests her face back on her hoof.
>"He really isn't coming back is he?"
"Wait, what? What are you talking about? You know what, never mind any of that. Why in the nine Hells are you out here in this god awful weather?"
>She looks you for a moment before motioning to the seat across from her.
>There is a cup with a straw in it across from where she's sitting.
>"He said he just had to run to the colt's room and he would be right back."
"How long ago was that?"
>She takes a deep breath and then lets out a loud wail before hiding her face in her forelegs.
>You're struggling to understand what she's saying between sobs
>"He said he would be right back. *Sniff* He.. he said it would only be for a minute or two."
>The realization of what happened hits you like someone stabbed you in the schlong with a pitchfork that had sharpened prongs.
>You walk over to her side slowly and gently place your hand on her shoulder.
>She jumps at the touch but doesn't ask you to take your hand away.
"What happened that has you sitting out here in the first place?"
>"I had a interest in one of the ponies in town and I asked him if he wanted to get something to drink and chat for a bit."
"I'm guessing that you guys got drinks and then something happened?"
>She looks up at you and smiles weakly.
>she looks so sad. It's crushing your heart to see the poor girl like this.
>"He..."
>She pauses and takes a breath.
>"He asked me about the rumors about how I drive away any stallion that takes an interest in me."
>Rumors? What rumors?
"Alright, so what happened?"
>"I told him how I always seem to have bad luck and just want to find a nice stallion that would be willing to greet me with a nice warm meal once in a while."
"That's not unreasonable I suppose."
>She nods eagerly, seeming to cheer up just a bit.
>"I know, right? I just want somepony... anypony to look at me like I'm worth SOMETHING."
>She starts sniffling and hides her face again.
>Oh no, not again.
>Your lips become a thin line and you narrow your eyes.
>You don't know what the story with this pony is but you aren't going to walk away and leave her sobbing in the rain because some asspull bailed.
"Nuh-uh. Not this time young lady."
>You shift your now cold food under your left arm and put your other arm around her midsection lifting her clear off of the seat.
>"Hey! Wait! Put me down!"
>She flails around trying to get free but your grip is strengthened by the force of your irritation.
"Hush up tiny pony, we're going home and I'm gonna make you food that will knock you off your hooves."
>She stops flailing the moment you mention making food.
>"You're going to cook a meal?"
>Walking down the street with cold, soaking wet pony under arm you grunt in acknowledgement.
>"A meal that you're sharing with me?"
>Another grunt.
>"You're cooking a meal for both of us. To eat at the same time?"
"Yes."
>"We're gonna eat it.."
>She pauses nervously for a moment."
>"...together?"
"That's right. You. Me. Food. Eat. You got a problem with that?"
>"Nope, just making sure."
>The rest of the walk is silent.
>With the exception of a few snickers and murmurs from ponies that you pass while carrying Cheerilee under arm.
>You don't even spare them a glance as you run home through the storm. She seems happier and you're finally getting some bomb ass KFC fries.
>All in all not a bad start to the evening.