Trouble With Dating

by TheAnimerican


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.