Trouble With Dating

by TheAnimerican

Rating: everyone
Tags: Applejack, My Little Pony: Friendship is Magic, Cutie Mark Crusaders, Romance, Pinkie Pie
Length: 8524

Trouble Shoes wants to ask out the mare of his dreams, but with his luck he will need all the help he can get.

Trouble Shoes wants to ask out the mare of his dreams, but with his luck he will need all the help he can get.

Also, I would like to give credit to snowzahedghog for allowing me to use this pic for the cover art. Please be sure to check out her page.

Published 2016-08-29 02:00:01 UTC
Last updated 2016-09-12 08:53:05 UTC

Cutie Mark Crusaders Assemble!

Sweetie Belle and Scootaloo sit in the club treehouse as they wait for Apple Bloom to join them. However, this time she is late and the rest of the Crusaders grow bored.

"I wonder why Apple Bloom isn't here yet. She is never late and she is the one that called for this meeting." said Scootaloo.

"I know. She said she wanted this to be a surprise. Maybe she isn't feeling well and couldn't come." Sweetie Belle replied.

Not long after they shared each other's opinions, the door opens and there is Apple Bloom with a big smile on her face.

"She looks fine to me. In fact, she looks just as happy as the day we got our cutie marks." Scootaloo stated.

"Girls!!! Guess who came to visit us today!?!" Apple Bloom shouted with excited. Which of course, it was unnecessary since Scootaloo and Sweetie Belle were just a couple inches away from her face.

"Is it Babs Seed?"

"Is it Countess Coloratura?"

"Oh how I wish they both came to visit, but nope!"

"Well, then who is it?"

Apple Bloom joined the Crusader in a line and faced towards the door. Scootaloo and Sweetie Belle were confused, but then heard heavy hoofsteps and had their attention towards the door. Soon enough, they see a large stallion's head peeking inside.

"Trouble Shoes!!!" Scootaloo and Sweetie Bello shout with excitement.

"Hi girls. I would come in, but it looks like it would be a tight fit."

"Oh. Right." Apple Bloom blushed in embarrassment.

They start to hear creaking sounds coming from underneath Trouble Shoes. He looks at the little fillies with a unamused expression.

"Figures."

Suddenly, the stairs collapsed underneath trouble shoes. The Crusaders quickly got off their flanks and ran to the doors and windows to check on Trouble Shoes.

He was conscious and looked at the fillies with an apologetic look.

"It's okay. We can fix it."

***My Little Pony: Friendship Is Magic Intro***

The Crusaders and Trouble Shoes decided to have their get together inside the Apple Family Barn instead until Big Mac and Applejack were done fixing the stairs.

"It is good to see y'all again girls. Sorry for the trouble."

"Oh it's no trouble," Apple Bloom replied, "We are just glad you're okay. How are things in Appleloosa?"

"Well the folks are still...careful of my cutie mark, but at least they don't have torches and pitchforks. Also, I still can't thank you three enough for helpin' me with my dreams of being in the rodeo."

"We were happy to help. It wasn't until recently that it was what we were meant to do," said Scootaloo.

"Yeah!" The Crusaders cheered in sync.

"Hehehe. Well, actually, that is kinda the reason why I'm here. I've been thinkin' a lot about somethin' and I was hopin' you three can help me again."

The cheerful expressions on the Crusaders faded into concern. "What is it?" Sweetie Belle asked.

"Well...there's this...mare-"

Before he could finish, the three fillies gasp in shock. Then, slowly a smile grew on their faces and let out a loud, "Aww!"

"You like somepony? That is soooooooo cute." Sweetie Belle stated.

"Well? Who is it?" Scootaloo asked in excitement.

"Is it somepony we know? Does she live in Appleloosa? Is she pretty?" Apple Bloom was showering the stallion with questions. They begin to notice that the stallion is blushing.

"Well...it's uh..."

The barn door opens and the Crusaders grow frustrated at the interruption. They look to see Applejack, covered in dirt and wearing her tool belt."

"Hoo-wee! It took a while, but me and Big Mac got them stairs fixed right up for ya."

"Thanks sis!"

"You okay there Trouble Shoes?"

Instead of answering right away, his blush grew redder and the sweat dripping from his head became noticeable. His face became so red that you might mistake him for Big Mac.

"Trouble Shoes? You are redder than our apples. Are ya feelin' alright?"

"Uh-Nope! Nope! I am just fine."

Applejack looks at him with confusion and then to her sister, hoping there was something she can tell her.

Apple Bloom looked back and forth between the both of them. Then it hit her like a wonder bolt. Quickly, she tried to think of an excuse, "Oh uh...he is feelin' a little under the weather. That's why he...broke the stairs! He felt real dizzy and knocked over them stairs."

"I thought y'all said it collapsed underneath him."

"Is that what we said? Oh we were just worried and probably changed the story."

"Worried? Worried about what?"

Apple Bloom quickly got up and started gently pushing Applejack out the door, "Well thanks sis for fixin' the stairs and checkin' up on us, but I am sure you and Big Mac are busy on the farm and I will help you later BYE!" The barn door slams and Apple Bloom gives a deep sigh of relief. She looks to Scootaloo and Sweetie Belle and sees looks of confusion on their face. Eventually, that same wonder bolt hit Sweetie Belle and looked towards Trouble Shoes with a shocked expression.

"Will somepony please tell me what's going on!?!" Scootaloo shouted in frustration.

"Trouble Shoes...do you...do you like...my sister?"

Unable to answer with a worried look on his face, he closed his eyes and nodded a yes.

"You like Applejack!?!" Scootaloo shouted. Sweetie Belle shoved her hoof in Scootaloo's mouth in hoping that Applejack didn't hear that.

Trouble Shoes took a deep breath and explained, "Ya know how I told y'all about how I would go to watch every rodeo? Well, when I was a young colt, I was watching what came to be Applejack's first rodeo. She was a little filly, but she was about the best darn thing I have ever seen at a rodeo. The way she can rope, the way she can buck, and her will is what got her through all them rodeos. I always cheered for her at each rodeo and was sad whenever she couldn't make one. When I saw her at the last rodeo, I was happy to see her perform and she was the most beautiful mare there. I believe it was around that time...I realized I had strong feelings for her..."

The Crusaders had their jaws dropped listening to Trouble Shoe's story. Apple Bloom was the first to snap out of it and placed a hoof on Trouble Shoe's hoof. "Don't worry Trouble Shoes, we'll help you. That's what friends are for. Right girls?"

"Right!" Sweetie Belle and Scootaloo cheer.

"But what can you three do? She is a amazing farm pony and I'm a messy klutz."

Apple Bloom gave a giggle, "Well I think I've got the solution. Sweetie Belle and Scootaloo can help you with manners and cleaning you up. I can help you with my sister. I know everything there is to know about her. What do you say Cutie Mark Crusaders?"

"Of course! Rarity and Rainbow Dash can help us as well!" Sweetie Belle exclaimed.

"Cutie Mark Crusaders helping Trouble Shoes! Yeah!!!"

Author's Note

I hope this story is okay. Please let me know if you guys have issues with my grammar. I would be more than happy to correct them. Also, if this story is similar to someone else's, I apologize in advance. Thank you!

Etiquette, Coolness, and Sister

***Carousel Boutique***

"You can't help!?!" shouted Sweetie Belle.

"I'm sorry Sweetie Belle," Rarity apologized, "but I must head back to Manehattan right away. Apparently, Plaid Stripes had another one of her good ideas. She thought it would be a good idea to create glow in the dark dresses. To make things worst, she chose the worst possible color...GREEN!!!"

Oh green, how she hated the color. Just the thought of it had gave her goosebumps. It gave her a reason to rush with her packing and travel lighter than she usually would.

"But Rarity, I promised my friend you could help him. Your charms could help him win the heart of his special somepony!"

"Oh that is sweet of you to say Sweetie, but I must go. I can't lose my boutique or let those dresses ruin my reputation." Rarity said with a dramatic tone. All she needed was her couch and maybe a violin playing in the background.

"Oh, look at the time, I am going to miss my train. I am sure your friend will do fine Darling. Just remember, he must be well-mannered and treat his special somepony like a princess. Also, be sure that he is cleaned up and well dressed for his date. Ta-ta!" Before Sweetie Belle could say anything, Rarity bolted out of the boutique without even closing the door. Leaving a disappointed Sweetie Belle behind.

"Well, at least Rainbow Dash can help."

***In the Field Near Cloudsdale***

"You can't help!?!" shouted Scootaloo.

"Yeah, sorry squirt. You caught me at a bad time. I have to report to the Wonder Bolts right away. They had an idea to perform a night show in Manehattan. They are short on fliers right now and there aren't enough reserves that studied the formation."

"But you are so awesome! I was hoping you can help my friend to meet their special somepony."

"Yes, it's true, I am awesome." Rainbow exclaims as she flexes her forelegs while flying in the air.

"I'm sorry Scoots, but they are counting on me and this is their first night show ever."

Scootaloo gives off a loud sigh, "Okay..."

"Cheer up little sis. Listen, whoever this friend of yours' is, if he really likes this special somepony, then he needs to approach her with confidence. He just needs to be cool and not place himself beneath her hoof."

"You really think so?"

"I know so kid. Well, I gotta go. Let me know how it turns out when I get back!" Rainbow Dash gives a wave goodbye and flies off.

"Ugh, well, at least Rarity can help us."

***CMC Treehouse***

"She couldn't come!?!" Sweetie Belle and Scootaloo asked each other in sync.

"What are we going to do? Trouble Shoes thinks we are going to bring his 'teachers' to help him." Sweetie Belle asked in worries.

"I don't know...who else can help us? What about Twilight?"

"Hmm...I think she will just look through her books. The last time we did that, we made a love poison."

"Oh, right. What about Fluttershy?"

"She is having her weekly tea party with her animal friends."

"Pinkie Pie?"

"He wants a date, not a party."

The two then went quiet and began to ponder at the situation. Sweetie Belle began to pace around the treehouse, while Scootaloo remained sitting on her flank. Then Sweetie Belle jumped with excitement as she most likely thought of a solution.

"Hey, why don't we be the teachers?" Sweetie Belle suggested.

"Us?"

"Why not? We both know our sisters and we kind of knew what they would do to help Trouble Shoes. So why can't we do it ourselves?"

"Hmm...I guess we could give it a try." Although Scootaloo didn't sound completely confident, she felt that they had no choice.

***The Apple Family Barn***

Apple Bloom continues to give advice to Trouble Shoes on her sister. He found most of the information very useful, but there was also a couple of things that she could have left out. However, he couldn't stop laughing at the story of Applejack eating all the apple fritter at the Apple Family Reunion. The thought of a little foal having such a large appetite was amusing to him.

"Hehehe. Does she still eat like that?"

"Well, when she eats at home she does. She tries not to eat as much when she is out with her friends. She says she is too embarrassed to eat like that in public."

The barn door slowly opens and Apple Bloom makes a run for the door.

"Hey girls, what took y'all so long? Is Rarity and Rain-" Apple Bloom quickly stopped herself when she noticed it was not Sweetie Belle or Scootaloo, but her sister Applejack.

"Is Rarity comin' over?"

"Sis!?! Uh, what are you doin' here?"

"Well I was takin' a break, but I heard a lot of laughin' comin' from the barn. Why are ya still in here anyway? Don't y'all want to go back to the treehouse?"

"Umm...yeah. Sweetie Belle and Scootaloo went on ahead. I stayed with Trouble Shoes to see if uh...his fever went down. Yep, he is all fine now."

Applejack tilts her head as she looks at Trouble Shoes up and down, giving her own quick examination. "He still looks feverish to me. His face is still all red."

Apple Bloom looks at Trouble Shoes and gave a look that obviously asked, "Seriously?" Trouble shoes gave an awkward smile in response.

"Apple Bloom, if he is this sick, then you should've told me in the first place. I don't want y'all getting sick. You go on and play with Scootaloo and Sweetie Belle while I take care of him."

"Y-y-you take care of him? But I-"

"No buts sis. Go on now."

Although Apple Bloom tried to resist leaving, Applejack was of course stronger between the two.

"What is with you today? Maybe you should go rest instead. You're lookin' a little pale." Applejack then closed and locked the barn door.

Oh no oh no oh no! This is bad! What's goin' to happen in there!?! Apple Bloom thought loudly to herself. While in her own world, she did not hear Sweetie Belle and Scootaloo approach behind her.

"Apple Bloom? What are you doing outside the barn? Where's Trouble Shoes?" asked Scootaloo.

"Girls! There ya'll are. Applejack is inside the barn and-" Apple Bloom pauses and looks around her two friends. "Where is Rarity and Rainbow Dash?"

Scootalo and Sweetie Belle give one another a quick glance before replying, "Uh..." Sweetie Belle began to say with a uncomforting tone, "They couldn't make it."

"What!?! Why not!?!"

"They both had business in Manehattan." Sweetie Belle answered.

"Umm...did you say Applejack is in the barn? By chance, is Trouble Shoes in there with her?" Scootaloo asked with a look of concern. Seeing as how Trouble Shoes acted when Applejack first walked into the barn, they can't imagine how he is acting with the two of them alone.

The Apology

Being a nervous wreck, Trouble Shoes did not know what to do or say in front of the mare that he so deeply admired and cared for. After locking the barn door, Applejack grabbed a bucket of water they kept inside the barn in case of a fire. Although the situation has never occurred, you could never be too careful. She then grabbed a towel from one of the hanging saddle bags. Swinging the towel around her neck and grabbing the bucket with her mouth, she walked towards Trouble Shoes.

Trouble Shoes' blood began to boil as Applejack stepped closer to him. He was hoping that Applejack would dump the bucket of water on him just so he could cool off.

When Applejack was a couple hoofs away from him, she then pointed to a pile of hay. "Lay down over there."

Curious at what she planned to do, Trouble Shoes timidly walked toward the pile of hay. As she asked, he laid down.

Applejack soon joined him and placed a hoof on his head. "Oh for pony's sake, you're burning up. Ya shouldn't have pushed yourself for the girls. I appreciate what you're doin', but they would've understood that you needed to rest." Oh if only she knew what was causing the fever.

"I noticed that you haven't said much since you came here. Well...at least not to me anyway...and I think I know why..."

Trouble Shoes had mixed emotions for this statement. He was worried that perhaps Applejack figured out his feelings for her. He wouldn't be surprised if she did. He felt she was able to read him like an open book; the way he has been acting. What confused him though was the way she said it. He wasn't sure if it was just him, but he could have sworn he detected some guilt in the mare's voice.

"You are upset with what I said when we last met aren't you?"

When they last met? Ah yes, the night when the sheriff and his deputies caught Trouble Shoes. That night, Applejack escorted him to jail and...some words were said...

***Season 5: Appleloosa's Most Wanted***

"No!!!" The Crusaders screamed as Applejack and the sheriff took Trouble Shoes away.

After a few minutes of quietly walking through the forest, Applejack broke the silence, "Now that we are away from the girls, I have a few things I wanna say to ya."

Not being able to look in the face of a pony he deeply admired, he kept his eyes forward and remained silent.

"I don't care if you remain silent, but you're goin' to listen to what I have to say!" Applejack said with a tone of anger and fury. "One of them fillies is my little sister and I could not stop thinkin' about what you might have done with them. Ya oughta be ashamed of yourself for fillynappin' those girls! What kind of pony are you!?!"

With every word spoken, Trouble Shoes' heart began to break. Time itself seemed to have been slowed down; just so he would be tortured throughout the walk back to town. How he wanted to explain himself to her, but would she have listened? Probably not. Who would listen to a criminal with the reputation of wreaking havoc at rodeos almost every year? He felt that cutie mark of his brought much bad luck in his life, but this moment had to be the worst kind of luck.

"I swear, in the name of Celestia, I will buck you to the moon if ya did anythin' to those girls."

"Alright, that's enough Ms. Applejack," the sheriff interrupted, "We're here."

The sheriff was first to enter his office. He was then followed by everypony else. Trouble Shoes was escorted to a cell, untied the ropes, and then locked him inside.

"Great job everypony! We caught ourselves a criminal. Yee-haw! Now y'all get some rest now for tomorrow's rodeo. Especially you Ms. Applejack. I'll stay here for the night and keep watch."

"Thanks again Sheriff," said Applejack. She then turned her eyes toward Trouble Shoes. Trouble Shoes still refused to look at Applejack. Instead, he chose to face the corner in hope that she doesn't see a grown stallion cry. "You enjoy the rodeo from your cell; where you can't hurt anypony anymore." Those words matched the atmosphere of that jail cell; cold. After her said words, she and the deputies left the sheriff's office. Alone in his corner, Trouble Shoes grit his teeth while tears streamed down his muzzle.

***Apple Family Barn (Present Day)***

There was a long moment of silence between Trouble Shoes and Applejack. Trouble Shoes was still lying down while Applejack had her hoof on his forehead with the wet towel. The whole time, Trouble Shoes had made no eye contact with Applejack. At this point, he worked up the nerve to turn his head towards her. What he saw caught him completely off guard. He saw that the mare's eyes were red and heavy amount of tears began to form. She was obviously trying to hold back, but was unable to do so.

"Be-before I left...I...I wanted to apologize...f-for what I said to ya." Applejack tried to explain with a large lump in her throat. "But...but...I was so ashamed...I have never talked to anypony like that in my life." Trying to continue, she closed her eyes and large drops fell onto Trouble Shoes' face. "In-instead of facin' you a-and telin' you I...I was wrong...I went straight home. I...I regretted it ever since." For Trouble Shoes, this sight was a lot to take in. Somepony so strong, yet at this very moment she looked so vulnerable. It is hard to believe that this is the same pony that said those things to him that night. "I-I'm so sorry...I'm so sorry." Applejack could no longer hold back. She let out her cries and tears were falling on Trouble Shoes as if it was starting to rain.

Trouble Shoes slowly got up into a sitting position in front of Applejack. Not able to find anything to dry her tears, he grabbed the towel she was using for his forehead. He squeezed out the water as best he could to make it dry enough. He then used it to try and wipe away her tears. Applejack's crying began to calm down, "T-thank you. I'm sorry. Hehe. I don't know where all that came from..." She wiped her eyes with her forelegs and dipped her hat. Although most of her crying was done, she still had a little left to give.

"Ms. Applejack, please don't be sad. I was never mad at you, I was just...so nervous to talk to you. If it makes you feel any better, I forgot all about that incident in the sheriff's office."

"You...you're just saying that..."

"No ma'am. As you said, Apple Bloom is your sister. I know that you would do anything to protect her."

"She is my family. When I saw her with ya...I wasn't thinkin' straight."

"I don't blame ya, but the point is...you have no reason to be sorry. In your hooves, I would have likely done the same thing."

Applejack continued to hide herself with her hat from Trouble Shoes. Eventually, she lifted up her had and looked at him with a small smile on her face. "...Thank you. Even if you're just saying it...I feel a lot better now."

Both ponies stared at each other silently. It wasn't long before Applejack remembered Trouble Shoes' so-called sickness. "Oh horse apples! I forgot about your fever. I will be back. We should have a bit of medicine in the house." Applejack quickly got up and headed for the barn door.

"W-wait, but I'm not-"

"It'll only take a sec." Applejack quickly ran out of the barn, almost slamming into the Crusaders on the way out.

"They were in there for a while. You think anything happened?" Scootaloo asked.

"I don't know. We better go check." Apple Bloom suggested.

The Crusaders walked into the barn to see Trouble Shoes sitting down and looking to the ground. At first, they believed that things didn't go well and he was depressed. However, they then realized that there was a small smile on his face. Sweetie Belle approached him and placed a hoof on his back. "Trouble Shoes, is everything okay?"

Trouble Shoes turned his attention towards the girls, "Hehehe. Everything is just fine."

Author's Note

I feel like in the second chapter, I went a little too fast. So I hope this third chapter was a lot better. Keep in mind, although this might sound like an ending this is not the last chapter. I hope you are all enjoying it so far. Please feel free to leave feedback, both good or bad. Thank you for taking the time to read this fimfic!

Good Luck

***Inside the Apple Barn***

"Wow, Applejack said that to you?" asked Sweetie Belle.

"She cried that much? Gosh, she hasn't cried like that since..." Apple Bloom didn't finish her sentence. She instead looked to the floor in silence; remembering that Applejack hasn't cried that much since their parents passed away. Apple Bloom's expression quickly changes from grief to excitement; at least she wanted it to look that way in front of her friends. "That doesn't matter, what matters is that you two finally got to talk to each other!"

"Yeah, but this isn't what I had in mind. She keeps thinkin' I have a fever. I want to talk to her and be friends, not have her be my temporary nurse."

"She will be in the barn taking care of you. Even if you aren't sick, how much closer can you get?" Sweetie Belle asked.

"Well, I can get a lot closer. I wanna...I wanna..." Trouble Shoes blushes again and could not keep eye contact with the girls.

"What?" Scootaloo asked eagerly.

"I wanna...ya know..."

Apple Bloom, growing a grin on her face, begins to tease the large stallion. "Nooooo, what do ya wanna do?" the mischievous pony asked.

"Eh...forget I said anything!" Trouble Shoes walked away from the girls.

"Aww, come on now. You can't start sayin' somethin' and walk away, what do you wanna do with Applejack?"

"Nothin' ya need to know."

"Oh, but we do!" Scootaloo said playfully.

"Talk to the flank." Trouble Shoes stated.

"Okay, while she does, I will talk to your face. What do you want to do with Applejack?" Sweetie Belle asked.

Pressured by the little fillies, Trouble Shoes decided to just blurt it out. "I wanna ask her out on a date!"

After saying those words, there was a loud thump sound hitting the ground. The three fillies and Trouble Shoes looked to the source of the sound. It's source was Applejack dropping her saddle bag with medicine. Trouble Shoes began to drown in mixtures of different emotions; the first was shock, the second was fear, and the third was regret. Apple Bloom, however, was feeling only guilt. Although she was just having fun with Trouble Shoes, she felt that she might have caused a wall to form between him and Applejack.

"W-...What did you say?" Applejack asked.

"I...I..." Trouble Shoes is paralyzed, but as least he was still standing. He couldn't believe that he blurted something like that out. They were starting off in the right direction, but now he feels like his cutie mark gave him the worst possible turn.

"You...you were goin' to...ask me out on a...date?" Applejack began to slowly step forward to the Stallion. The Crusaders stepped to the side as she soon became a couple hoof steps away from him.

Trouble Shoes looked to the Crusaders in a obvious cry for help, but they were unable to provide him any at that point. The most that they were able to do for him was be there for him. Trouble Shoes then looked back into Applejack's eyes that were waiting for his answer. At that point he thought, "Oh buck it!."

"Ms. Applejack, I was hopin' you could do me the honor...of being my date tonight." Trouble Shoes asked in fear of rejection, but with confidence as well.

Applejack's face expression never changed. She was not expecting something to surprise her like that since it took so much out of her to apologize. Her knees began to shiver and was afraid of collapsing. Trouble Shoes and the Crusaders notice her losing her balance. Although they were prepared to catch her, she regained her composure and regained eye contact with Trouble Shoes. "I'm sorry, but...I can't..."

Trouble Shoes had prepared himself for those words, but it is never easy hearing the real thing. The Crusaders too began to feel hurt by the words.

"But...I wouldn't mind tomorrow night."

Trouble Shoes and the three fillies instantly snap out of their sad state of mind.

"I'm pretty tired from all the chores and...this is might sudden, but I would like that."

On the inside, he is experiencing a powerful feeling that could not be expressed into words. Rather not say anything stupid, he kept silent to not ruin this moment. Instead, they stare into each other's eyes; both of them having a smile and redness in their cheeks.

"Uh, it seems you have a fever of your own." Trouble Shoes said jokingly.

Applejack gave a small chuckle and the Crusaders giggled in the background.

"Well, this has certainly been an interestin' day for the both of us."

"Hehehe. Yup."

"Well, I guess I'll be gettin' along to bed. If ya have no place to stay for the night, we have a guest bedroom."

Applejack looks towards the girls, "Apple Bloom, can ya show him the guest bedroom? Also, it is gettin' late, you three can have a sleepover tonight."

"Yeah!" The three cheered in sync.

"Thank you Ms. Applejack," said Trouble Shoes.

"Hehe. Just call me Applejack. I'll see ya tomorrow...sugar cube." Applejack walks out of the barn and out of sight.

After they knew the coast was clear, the Crusaders jumped for joy and jumped on Trouble Shoes.

"You did it Trouble Shoes!" yelled Apple Bloom.

"You two are going on a date!" cheered Sweetie Belle.

"Yup, I'm going on a date...Oh sweet Celestia...I'M GOING ON A DATE!?!" Trouble Shoes screamed in a panic.

Here Comes Trouble

***The Apple Family Barn***

Early the next day, the Cutie Mark Crusaders have Trouble Shoes meet in the barn. In the barn, there is a table set up with a candle lit in the center. Apple Bloom sits on a stool, wearing a hat similar to Applejack's on one side. On the other, Trouble Shoes sits between Scootaloo and Sweetie Belle.

"Why do I have to pretend to be Applejack?" Apple Bloom asked.

"Because you are her sister. You are the closest thing for Trouble Shoes to practice." Scootaloo answered.

"Listen girls, I do appreciate what y'all are tryin' to do here, but are y'all sure about this?"

"Of course Trouble Shoes. You want to win Applejack's heart don't you? Practice makes perfect." Sweetie Belle replies.

"Now what Rainbow Dash told me, was that you should not put yourself underneath somepony else's hooves. You have to be confident about yourself. Otherwise, you will keep worrying that you are not good enough for her." Scootaloo advised.

"But she's a rodeo champion and I'm a clown!" Trouble Shoes protested.

"You see? With that kind of attitude, you will never win her heart. She might be a great rodeo champion, but she is still a mare."

"Wow Scootaloo, that was actually a good lesson to teach." Apple Bloom complimented.

Scootaloo blushes at the compliment, "Hehe. Thanks. At first, I didn't understand what Rainbow Dash meant. I understood after seeing Trouble Shoes ask out your sister. I thought it was very brave of him and he asked with so much confidence."

Trouble Shoes dips his hat to try to cover his muzzle, but the little fillies were still able to see redness on his face.

"Rarity provided good advice too. She told me that you need to treat your special somepony like a princess. Remember that Applejack is like any other mare, but just about every girl likes to be treat like a princess." Sweetie Belle advised.

"And my sister deserves to be treated like one." Apple Bloom exclaimed.

Scootaloo and Sweetie Belle look at Apple Bloom with a unamused look. As true as that statement may be, they were clearly telling Apple Bloom not to put pressure on Trouble Shoes. Apple Bloom returns their reaction with a small smile that said she was sorry.

"Okay. Now here is the scene, you are on your first date with Applejack at a restaurant. Play it out like what you might do on an actual date. Apple Bloom, try to act out your sister as best you can." Scootaloo directed.

Apple Bloom gave a wink, "Got it!"

"Date starts...now!" Sweetie Belle announced.

Despite the announcement, neither side of the table has said anything. Then, they waited...and waited...and waited. Although it was probably only a few minutes that passed, it will feel like forever on a actual date.

"Aww come on!" Sweetie Belle's signature line, "Why aren't you two talking? Apple Bloom, I am sure Applejack would say at least one word. Trouble Shoes, is this how you want your date to be?"

"I'm sorry, but...I don't know what to say." said Trouble Shoes and an apologetic expression.

"How? I told ya a lot of things about my big sis yesterday."

Trouble Shoes gives a deep sigh. "Ugh, what was I thinkin'? I ask her out and I can't even act out a play. I didn't think she was gonna say 'yes.'"

Sweetie Belle and Scootaloo comfort Trouble Shoes by giving him a group hug. "Don't sell yourself short Trouble Shoes," says Sweetie Bell, "Applejack wouldn't have accepted you if she didn't like you."

"Yeah. You are thinking too much on it. Just remember to be confident. The way you are talking to us right now, try talking to Applejack the same way." Scootaloo suggested.

Trouble Shoes thought it over, but soon his face was covered with confidence. "Alright."

"Great! Date with Applejack, take 2!" Sweetie Belle announced.

After the announcement, there was still a moment of awkward silence. Sweetie Belle and Scootalo were looking at each other with annoyance, but then they heard a sound break the silence.

"Uh...you look very nice tonight." Trouble Shoes complimented.

"Thank you Trouble Shoes. Ya look nice too."

"That's good Trouble Shoes! Keep it up!" Scootaloo cheered.

Trouble Shoes gave a smile and the look of appreciation to all three fillies. He then continued practicing with Apple Bloom.

***Few Hours Later***

"Whew. Girls, can we take a break. I don't think I can go on another date." said Apple Bloom.

"I thought Trouble Shoes was really sweet to Applejack the entire time. Although, there might have been a accident or two with the waiters and waitresses. Besides all that, I think he is ready for the date." Sweetie Belle said. "But there is one thing left to do."

At first, Trouble Shoes looked at Sweetie Belle with confusion. It was soon changed to worry as he sees Sweetie Belle with a make-up kit, fabric, and sewing equipment. "Just a few changes. You will need to look good for your date tonight. Girls, can you lend me a hoof or two?"

***Date Time***

"I gotta say Sweetie Belle, ya might not be good with fabric, but ya sure know how to groom a pony." Apple Bloom complimented.

"Well thanks to you, he has a fitting suit. The available suits Rarity had at the boutique were too small, but with your help we were able to adjust it to a proper size for him." Sweetie Belle complimented.

Trouble Shoes stands tall in front of the fillies in his newly made suit. Plus, his hair is well groomed and shaved off any facial hair that he had. "This has to be the nicest suit I ever had...This is the only suit I ever had."

"You look great! Now, you just need to pick up your date." said Sweeite Belle.

Yes, picking up his date. A night that Trouble Shoes both looked forward to and dreaded. "Uh...umm...I think I really do have a fever. I am sick to my stomach and it is really hot in here."

"You're just nervous." Scootaloo stated. "You came all the way to Ponyville for her and you practiced all morning for her. You are ready. Right girls?"

"Yeah!" Apple Bloom and Sweetie Belle cheered.

Trouble Shoes gave a small smile, "Thanks. You three are somethin' else." He brought the girls in for a group hug. After letting them go, he walked out the barn and went towards the front door of the Apple Family House.

***Apple Family House***

Trouble Shoes takes a deep breath and it about to knock on the door. However, his vision is interrupted by a floating bouquet of flowers. He looks around and sees three fillies hiding in the bushes. One of them being a unicorn with her horn surrounded by a light green aura. He gives a smile and then grabs the bouquet. As quickly as he had the courage to knock on the door, he just as quickly got nervous after hearing hoofsteps heading to the door. His mind began to race. Like a new actor, starring their first role, he is forgetting what he planned to say to Applejack. When the door opens, he closes his eyes and shoves the bouquet of flowers in the muzzle of the pony. "These are for you!" He yelled in panic.

"Oh these are nice flowers sonny." What he heard was not Applejack, but an older country voice. He peeks by opening one eye and sees that it wasn't Applejack, but it was Granny Smith. He can hear the small fillies giggling in the background at this major mistake.

"Oh-uh-you see-I-well-they're-" Trouble Shoes juggling with his words.

"Oh hey Trouble Shoes! Those are nice flowers." Now that sounded like the voice he wanted to hear. Although she was still out of sight, he knew it was Applejack somewhere inside the house.

"So...them flowers ain't for me?" Granny Smith asked.

Not wanting to be rude, Trouble Shoes replies, "Umm...of course they are. Apple Bloom told me that ya liked flowers."

"Ah well, that's awfully nice of ya sonny. I will put these in a vase." Granny Smith takes the flowers and heads back into the house.

Applejack soon fills in the spot where Granny Smith was. Trouble Shoes was left speechless at the sight of her. First of all, he never thought he would see her without her mane band. Instead, her mane runs straight with a curl at the end. Also, she was wearing a green dress with some apple décor. Applejack takes notice that Trouble Shoes was staring, "Sorry, is this too much? Apple Bloom insisted that I wear somethin' nice."

Remember, treat her like a princess, Trouble Shoes thought to himself. "Ya...ya look beautiful..."

It was obvious that the compliment caught Applejack completely off guard. Her face blushed red and she could not keep eye contact with him. "Umm...thank you...Ya look...handsome."

In a way, Trouble Shoes felt like she evened the score. Both ponies were blushing and were not sure what to say after that.

"By the way, were them flowers suppose to be for me?" Applejack asked.

Trouble Shoes replied by giving an awkward smile and blushes.

"Hehehe. I thought so. That was really sweet of ya. Sorry about Granny."

"Um...no. No trouble at all. Are ya...ready to go?"

"Mhm." Applejack stepped out and closed the door behind her. She and Trouble Shoes walked side by side as they left the ranch. While they were walking, three fillies secretly followed behind them.

Date or Bust

***Traveling to Sugar Cube Corner***

Trouble Shoes and Applejack made their way to Sugar Cube Corner. As they were walking, they couldn't help but notice that other ponies were staring at them. In Ponyville, you rarely see Applejack without her friends. Let alone seeing her in a dress or with a random stallion that the town has never met before.

"Uh, is it just me or is everyone starin' at us? Like they've never seen a couple on a date before." Applejack said with a hint of annoyance.

The thought made Trouble Shoes' heart skip a beat. This was really happening, Trouble Shoes was on a date with the mare of his dreams. He was sure that many ponies in Appleloosa would envy him if they ever witnessed this. Slowly, the confidence he had while leaving the farm was slowing beginning to fade. Suddenly, he remembered what Scootaloo told him, "Don't put yourself under her hoof. She is still a mare."

"It's probably cause they don't see ya in a dress too often."

"Hahaha. That's true. I never thought of that."

Finally reaching Sugar Cube Corner, Applejack enters through the already opened doors. Trouble Shoes follows behind her and is soon greeted by a pink pony. "Why hello there! I never seen you before. I'm Pinkie Pie and welcome to Sugar Cube Corner! A new pony in town always calls for a P-!" Before Pinkie Pie could finish, Applejack shoves a hoof in her muzzle.

"Om Mhi Abblejack." Pinkie Pie attempted to speak with the hoof still in her mouth.

Applejack takes back her hoof. "Howdy Pinkie Pie. Sorry about that, but we don't wanna big party tonight."

"What? How could you say that? How How How How HOW can you ask me not to give him a party?"

Applejack blushes slightly, "Well...ya see um...we are...on a date." Applejack tilts her head to the floor with a small smile.

Pinkie Pie releases a loud gasp and grabs both Trouble Shoes and Applejack in a hug. "That is great Applejack! Oh Oh Oh! I will be your waitress for tonight!" Still holding both ponies, Pinkie Pie drags them to a personal table by the window. She closes the curtain to make the room slightly darker. With her quick speed, she ran to the kitchen and back to the table. She rolls out a white table cloth on the table. As the cloth unrolled, tableware appeared; plates, food utensils, cloth napkins, and a glass of water appeared on each side. In the center of the table, a candle stick is lit.

"Pinkie-how did-?" Applejack flabbergasted at the table setting, she stopped herself and remembered exactly who she was talking to.

"Don't worry Applejack, I will make sure NOTHING will ruin your night!" After saying so, Pinkie saw a group of ponies approaching Sugar Cube Corner. Quickly she ran to the door before the group could enter. She shouts at them, "We're closed!" She then shut the door and locked it.

"Oh Pinkie, ya didn't have to-"

"Oh don't worry Applejack, Mr. and Mrs. Cake are out of town with their little foals. I'm in charge tonight! Oh, I know exactly what to make you two!" Before Applejack could protest, Pinkie Pie ran to the kitchen and disappeared out of sight. Without the presence of Pinkie Pie, it became very quiet.

"Is she always this...?"

"Hyper?"

"I was gonna say prepared."

"It doesn't matter when or where, she seems to have everythin'."

Both ponies shared a giggle. Both ponies noticed that they still have their hats on and take them off; trying not to be rude.

"Did the girls talk ya into Sugar Cube Corner?"

"Well, I don't know my way around here. I asked if they knew any good restaurants. This isn't what I had in mind."

"Hehehe. It's alright. I like comin' here with my friends. It is probably my favorite place to eat in all of Equestria."

Whether she was saying that to be nice to Trouble Shoes or if she meant it, it certainly made him more comfortable.

"Bon appetite!" Pinkie Pie returned with many different types of food. Most of the dishes would be seen on the dessert menu. Pinkie Pie made everything from cake to cookies. She quickly set the plates on the table in a neat and orderly fashion.

"Thank ya kindly Pinkie Pie."

"Yeah, this looks delicious Ms. Pie."

"Ms. Pie? Hahaha. Oh just call me Pinkie! Any friends of Applejack is a friend of mine!"

As Pinkie was about to leave, she noticed that there was still a large gap on the table. "Oh! Silly me, I forgot the apple pie! Made with the apples of the Apple Family Farm!" Pinkie cheerfully trots to the kitchen.

Trouble Shoes whispers to Applejack, "I might be a big stallion, but I don't think I can eat all this."

Applejack smiles and whispers, "Don't worry about it. She does this all the time. She usually eats the left overs and doesn't get sick."

While they were sharing their giggles, they heard a thump sound coming from the kitchen. From Applejack's angle, she was not able to see the cause of the sound. However, Trouble Shoes was able to see a rolling pin near the entry way of the kitchen.

"Found it!" Not paying attention, Pinkie Pie was walking towards the table, but began to slip on the pin. Trouble Shoes, acting instinctively, got up to try and assist Pinkie Pie. However, instead of Trouble Shoes going to Pinkie, Pinkie went to Trouble Shoes. Pinkie rolled her way to him and slammed the Pie in his face. The force caused Trouble Shoes to fall back and fall back on the table. Applejack reacted by ducking underneath the table and Trouble Shoes rolled over and fell through the window.

Still trying to figure out what had just happened, he soon began to hear laughter all around him. He quickly got on all fours and wiped his muzzle to get a clear vision. He was surrounded by the ponies of Ponyville and laughing at him. All around him, was the former many desserts of Pinkie Pie. He became overwhelmed with embarrassment and depression soon followed. He turned around to see Pinkie Pie and Applejack through the broken window.

"Oh no oh no oh no. I'm so sorry! I didn't mean to." Pinkie was saying with a apologetic expression. She felt so bad that even she was on the brink of crying. Applejack just looked at him with a look of feeling sorry for him.

Don't look at me that way. Please... Trouble Shoes thought to himself. This was a time he really wished that he wasn't a rodeo clown. As he was about to walk away in shame, the laughing stopped. Confused, Trouble Shoes noticed that they were looking behind him. He turned around to see Applejack jump in the mess of desserts. She rolled until she was covered in sweets and her apple scent disappeared. She then walked to Trouble Shoes with a smile and said, "Now we match."

Trouble Shoes was shocked. She ruined her dress just so that he wouldn't feel embarrassed. The embarrassment and depression was soon washed away by the warmth provided by her. Before he could say a word, he heard a sound from behind that resembled a splat. He turns to see one of the ponies, a random Pegasus, have his face covered in ice cream.

"Food fight!!!" Pinkie Pie yelled and continued to throw her food. The ponies smiled and ran to grab some of the dessert on the floor. Applejack and Trouble Shoes looked at one another. Applejack gave a playful grin and joined in on the fun. At first, Trouble wasn't sure what to do, but after Applejack hit his muzzle with some cake, the decision became very clear. He quickly retaliated by grabbing the closest food he could find. The ponies food fighting, could easily be compared to a fillies' snowball fight. There was laughter and there was a mess.

***Walking towards Sweet Apple Acres***

Both ponies were following the trail to Sweet Apple Acres. Still covered in different desserts, they were both laughing and joking about their night.

"Hahaha! Did ya see the look on Mayor Mare's face?" Applejack asked.

"Hehe! How could I? You covered it in chocolate pudding!" Both burst in laughter.

"Hahaha. I haven't laughed like that in a long time."

"Me neither. That was my first food fight."

"Hehehe. Mine too."

As the two were laughing, they walk over the crest of a hill and see that they have almost reached their destination.

Trouble Shoes was disappointed. He was having so much fun that he did not want the night to end. As he was about to keep walking, he was stopped by a hoof.

"Wait, Trouble Shoes, there was something I wanted to show you."

Applejack had Trouble Shoes follow him between the trees. Through the trees, they were moving uphill. Although the branches of the trees were a little thick, Trouble Shoes was still able to see parts of the sky. The gaps in the branches provided enough light to provide a trail for the two ponies. However, through their walk, he was sure he heard other hoofsteps behind him.

"Umm...Applejack, not that I'm complainin', but where are we goin'?"

"You'll see."

Being taller than Applejack, Trouble Shoes was able to see ahead of her. Ahead of her, there was a break in the forest trees.

After they finally made it out of the forest, there was a large apple tree on top of the hill. Although, Trouble Shoes has seen the many apple trees in Sweet Apple Acres, none of them were as big as the tree before him.

Applejack sits in front of the tree and leans back. She motions for Trouble Shoes to sit beside her. When he walks to her position, he notices the view that the hill provided. When he looks to the left side of the hill, he could easily see Sweet Apple Acres. To the right side of the hill, he can see the town of Ponyville and Twilight's Castle beyond that. After taking in the scenery, he sits beside Applejack.

"This is my special spot. I always come up here when I need to think or if I just want to be alone."

"There are times when ya need to be alone?"

"Well, I wish I could say 'no,' but it ain't easy bein' a farm pony. It gets stressful workin' on the farm. Although I like hard work, there are times when it can become too much. I just...need time to be with...my parents."

"Your parents?"

"This tree here, this is the first apple tree they ever planted. Granny Smith helped them and it became their first tree. This tree...is all I have left of them..." A lump grew in her throat and tears began to form.

"I'm...sure your parents were nice folks."

She wiped away her tears and cleared her throat, "Yeah...they sure were..."

A apple fell from the tree and hit Trouble Shoes on the head. The apple bounced off and fell between his hooves.

"Hehehe. Well they seem to like you."

Trouble Shoes blushed and scratched the back of his head. Suddenly, he felt something pressing against his cheek. It took him a while to process what was going on. With a slight shift of his eyes, he was able to see that Applejack was kissing him. His body went numb and his body temperature sky rocketed.

After Applejack was done with her surprise, she noticed how red Trouble Shoes was and couldn't help but giggle. "Don't tell me ya catchin' a fever again."

"Maybe a little..."

Applejack stood up, "Well, we best be gettin' back."

Trouble Shoes stood up. He couldn't even attempt to hide the facial expression of disappointment that the night was almost over.

"AND I EXPECT TO SEE THREE FILLIES ASLEEP WHEN I GET BACK!" Applejack yelled in the direction of the forest. After doing so, there was rustling in the bushes and small voices scrambling.

"I thought I heard somethin." said Trouble Shoes. "How long do you reckon they were followin' us?"

"Probably the whole time, but I didn't notice until the walk up here."

She then turned her attention towards Trouble Shoes, "This is probably the most fun I had in a while. Even if it isn't how you practiced."

Trouble Shoes blushed in embarrassment. Applejack then joined him by his side, "Ya know...it's nice to have an escort for a change."

They began their short trip back to Sweet Apple Acres. To make this moment last, Trouble Shoes was purposely walking at a slow pace. It did not take long at all for him to know that this night was definitely the luckiest night of his life.