It was the date they'd agreed upon and Troubleshoes sat at a table in the small country–style restaurant they'd chosen, nervously awaiting Applejack's arrival. He'd only been sitting there for a couple of minutes and had enjoyed a live folk-country song before she arrived, and as she walked in, his jaw nearly dropped.

Applejack had her mane down for a change from the braid she usually wore it in, instead letting it flow naturally over her shoulders, with it going all the way down to mid–foreleg. She wore no makeup or jewelry, and such would have been an insult to her natural, rustic beauty anyhow. She also wore a basic, non-embellished forest-green frock. There was nothing fancy about it, but nothing could compliment her natural beauty more than such a simple accent, Applejack seeming to be one of the rare types whose beauty fancy clothes only tarnished instead of enhanced.

As she saw him, Applejack smiled and joined Troubleshoes at their table – and as she sat down her stool collapsed under her, making her end up on her back with hooves bent at her chest and her eyes wide in surprise. Everypony in the restaurant stared at her as the music stopped with a screech of a fiddle, the entire restaurant suddenly completely silent.

"M-Miss? Y'all 'right?" a stallion's voice asked, Applejack seeing a cream-colored hoof being offered to help her up. A passing waiter was the first to come to her aid, asking if she was OK and then apologizing extensively over what had happened.

"Ah—Ahm fine. Dun worry, just wanted t' see if the floor was as comfy as it looked." Applejack cracked uneasily as she quickly stood up by herself, feeling everypony's eyes on her and not exactly liking being the center of attention in this respect. Once everypony heard she was OK however, conversations at tables slowly started again, the band started another song, and the other patrons once more continued their meals. The waiter quickly brought Applejack a new stool alongside a couple of menus before leaving them to decide their meal, promising them a free appetizer platter of green-bean fries and hushpuppies with dip in apology for the incident.

~

A few minutes and a couple of mugs of hard apple cider each later, as well as finishing off both the appetizers, the two ordered, with Applejack ordering a simple 'floral bouquet' salad with extra daffodils and grass, and Troubleshoes ordering a bowl of hearty five–bean vegetable chili, with both dishes coming with the restaurant's "famous" cornbread.

As they waited for their dinner to arrive, Troubleshoes asked Applejack about herself and quickly learned that she was in fact THE Applejack – embodiment of the Element of Honesty and co–owner of Sweet Apple Acres, the largest farm in Ponyville! Troubleshoes then realized just what a catch he had and instantly regretted that she'd wanted to date him, given what had already happened to her from being around him. If his previous luck with mares was any indicator, the broken stool was very likely only the first thing to happen to her tonight.

After some more talk about her adventures with the other Bearers of the Elements and some light talk of his and her personal lives, their food finally arrived. The salad was placed before Applejack first, with her eagerly anticipating digging right into it, not having had time to eat since breakfast that morning. When the waiter suddenly, accidentally, over-exaggerated his bend as he sat down the basket of cornbread, it sent the bowl of thankfully-only-warm chili sliding off the tray – and landing cleanly onto Applejack's head.

Once again the restaurant went silent, another fiddle squeal bringing a screeching halt to the restaurant's sounds again. Troubleshoes could see the burning blush on Applejack's face even under the dense brown goop as she undoubtedly felt the eyes of everypony on her again, the thick chili slopping off of her muzzle and mane. She then quickly, and surprisingly calmly, excused herself to go clean up, leaving a trail of brown chili drips all the way to the washrooms.

The waiter once again apologized extensively for his carelessness, offering Troubleshoes not only free replacements for their food and free dessert, but also half-off their next visit. Toubleshoes accepted melancholicly but had a bad feeling abut them staying. This evening had an uncanny resemblance to his previous first dates, and he knew just how those relationships had ended up.

~

Applejack returned to the table shortly after, her light rose-scented perfume now instead replaced by the much less romantic and much more delicious scent of cumin, cilantro and tomato. Her mane and coat looked a few shades darker thanks to its greasy chili-bath and her frock was likely ruined, splotches of brown and grease now staining the fabric. Even still, she sat down on her new stool to resume her date – only for it to once again cripple under her weight, sending her once more sprawling onto her back.

That was the last straw for her; she'd been embarrassed enough for one day! Applejack promptly got up and stomped out of the restaurant, leaving a very concerned Troubleshoes alone at the table. With a sigh, he lowered his head. It was only the first hour of the date and he'd likely already lost her. "Just my luck" he muttered softly under his breath, then called the waiter for the check.

~

After he tried to pay for the drinks, he was told they were on the house, given a rain check for their two next meals to be completely free, and another two for two free desserts, then was followed out the door by a string of apologies.

As Troubleshoes stepped outside and heard a faint sniffling coming from the side of the building, he quickly followed it until he saw the profile of Applejack sitting on the curb, her muzzle down-facing. He heard the soft sniffling coming from her as she struggled to contain her tears, only to fail as a single wet drop streamed down her muzzle then fell to the earth.

Upon hearing hoofsteps, with Troubleshoes not being a small or quiet pony by any means, Applejack looked up for a moment before she lowered her muzzle again upon seeing it was only him, that brief glance of her upset eyes instantly sending a pang of guilt through Troubleshoes. His bad luck had caused this, after all. His bad luck had made this mare cry. "Ahm—Ahm so sorry..." Troubleshoes started, "Ah knew this date was a bad idea from th' moment Ah agreed, with mah bad luck an' all. Ah think Ah should jus' go now, before Ah cause anythin' else to happen to ya..."

Applejack looked up at Troubleshoes again, her small smile and gentle gaze instantly telling him that she wasn't upset with him. But how? He'd caused all of this! Applejack cleared her throat before she spoke again, "Now don't you worry 'bout this Sugarcube. It ain't yer fault any'a this happened. It was jus' bad luck, af'r all. Ah mean, y'all can't exactly prevent accidents from happenin' now-and-again now can-ya?"Applejack finished with her light smile remaining, wiped her nose with her hoof, then stood up and got closer to him. Suddenly, Applejack cuddled against him, burying her muzzle into his chest and nuzzling against him. "...an 'sides, Ah still like ya. That should count fer somethin', right?" Applejack asked, her voice soft and even-toned...if a bit risque!

Troubleshoes was surprised by Applejack's sudden actions, but by no means displeased. He lowered his head to rest behind Applejack's, his large size preventing him from embracing her properly and instead making him have to settle with placing his muzzle around the back of her head. When Troubleshoes heard a quiet, pleased nicker from her, he felt his heart flutter as she continued to nuzzle into his chest, with him in turn leaning slightly forward – only to lose his balance and fall forward, sending both careening to the dirt ground behind them.

Fortunately for both of them, Troubleshoes managed to avoid crushing Applejack beneath himself, but he still managed to drag her down with him, with both landing into the dirt and kicking up quite a dust-cloud. Applejack came up coughing with Troubleshoes following shortly after, the dust–cloud quickly dissipating with the gentle wind blowing it away but nevertheless leaving both ponies coated in a thick layer of dirt now. Applejack's wet frock now looked like she'd rolled in a pigsty with it given she was still damp from cleaning the chili off of herself, her loose, wet mane and tail completely and totally filthy, clumps of mud now throughout it and making her look like she'd had a wrestling match with a pig.

Troubleshoes feared the worst as Applejack stood up, wearing a very displeased look on her face. When she started laughing however, Troubleshoes was totally shocked. That was the absolute LAST thing he'd expected to hear from her! "Th—thi—this is the worst date Ah—Ah've ever been on!" Applejack exclaimed, barely managing to given how hard she was laughing. Troubleshoes contributed a few uneasy chuckles while Applejack fell on the ground laughing, his eyes darting back and forth as he became very uncomfortable at Applejack's admission that this was indeed a horrible date for her.

After Applejack calmed down some seconds later, her laughs turning to giggles, she looked to Troubleshoes – and suddenly tackled him. Despite him being much taller then her and thrice her weight, Applejack caught him offguard and caused him to fall backwards and onto his back, his landing kicking up another dust cloud and leaving Applejack now atop him and sitting on his chest. Before Troubleshoes could even react, he felt a soft pair of lips on his, looking up with wide eyes just in time to see the beautiful mare closing in before her lips met his, her eyes closing on contact. He felt a pleasant tingle rolling through him as she then held the kiss, softly moving her head side to side and sending another thrill up his spine.

After a few seconds, Applejack broke the simple kiss, instead looking into Troubleshoe's eyes and giving him another soft smile. "The. Ab-so-lute. Worst. Date. But despite it bein' the worst, by-hay it's the most FUN one! Tha last couple dates Ah went on were with a couple of snooty-snobs who only took me t' some fancy–pants restaurants and wanted me t' eat fish eggs. FISH EGGS FER PONIES SAKE! Ah mean fer corn's sake, wut kinda pony eats—" Applejack said with a snort of disgust, then cut herself off as she noticed she still had Trouble pinned beneath her. "Oh, uh, sorry."

After she got off of Troubleshoes and he got up, Applejack smiled as she got an idea. "Hey, instead of goin' to another restaurant, hows'a 'bout we go back to mah place an' Ah cook us up somethin' instead? Ah can whip up a mean spicy black-bean and rice casserole!" she offered, then looking to Troubleshoes for a response.

Troubleshoes was once more left in awe: this mare, this Bearer of an Element, hero to all of Equestria time and time again and successful farm co–owner, was now offering him not only for him to come to her home...but to cook him a meal as well, even after what had just happened?! Surely he was dreaming right? Surely no mare could be this amazing.

"Y–y'sure about that? Ah mean, this evenin' was jus' a total disaster. Wouldn't you rather jus' go home alone and ferget 'bout unlucky ol' Troubleshoes like every other mare has?" Troubleshoes asked melancholicly, but shortly after found a comforting hoof against his foreleg.

"Sugarcube, di'n't Ah say Ah still liked ya? This date's been the most fun Ah've had in quite a while anyhow! Most'a my days consist of weedin' fields, buckin' trees, er both. This is like a breath a fresh air t' me." Applejack said, following it with a gentle chuckle. "If this is yer 'bad luck', it sure is fun!"

Troubleshoes couldn't help it as a single tear streamed down his cheek, with him once again stooping down to wrap his muzzle around Applejack's neck. Never before had he felt so fully accepted by somepony as he did by this mare, and before he even knew what he was doing, he'd taken a mouthful of her mane into his mouth and had started to groom her, sifting the mud clumps out as best as he could and getting a slight gasp from Applejack. She was by no means uncomfortable with it, but it was so unexpected!

Troubleshoes continued for a few more minutes as he groomed Applejack, carefully cleaning her mane out and leaving Applejack speechless. She hadn't been groomed by somepony like this since her parents did it when she was still a filly! Applejack felt a twinge of sadness as she remembered her parents, then quickly shifted her focus from sad memories and instead to the lightly-pleasant feeling of Trouble gently tugging her mane as he got the dirt-clumps out, not wanting to mar this moment with painful memories of her past.

As he finished a short while later, Applejack gave Troubleshoes another nuzzle. "Thanks fer that, but y'really didn't need to. Ah've got a shower back at th' farm after all." she said, feeling a light burning in her cheeks. She was blushing, but had no idea why. "So, uh, anyhow. Sugarcube, didjya wanna come back to my place fer dinner, er...?" Applejack asked again, soon after getting a stiff nod from Troubleshoes. He knew this was a bad idea, but also knew that giving up an opportunity like this would be his biggest regrets of his life if he simply left. To leave such a beautiful, important mare with such a wonderful personality without even trying to make the blooming relationship work, that would be darn near criminal!

"Ah–right, y' just follow me big boy." Applejack said with an almost-seductive tone that instantly perked Troubleshoe's ears up. Surely he was imaging things. No way she was...coming onto him?

Author's Note

Best first date. 10/10.