An Unconventional Challenge

by RaijingtheClockworkPony


Thoughts on the Matter

Citrus. That was the first thing that Applejack could taste when the white stallion had kissed her, their tongues wrestling for domination. He tasted like citrus. Must be his tooth paste. Ah would have thought him a mint kind of pony. Applejack closed her eyes and gave herself up to the kiss for what felt like a small eternity with Elusive but as she reopened her eyes she pushed away from him.

She tried to regain control of her breathing for a few moments as she noticed the disappointed look on the stallions face.

"What in tarnation was that about?"

Elusive took a small step closer to her. "I was showing you how I felt about you." A worried expression came over his face. "You don't feel the same way?"

Applejack was about to tell him no but her mind had gone to the almost bliss like sensation of his lips on hers. She bit her lip for a moment and looked off to the side to avoid his gaze.

"Ah... Ah kinda do."

Elusive stood there for a moment. "Kinda? What do you mean?"

She looked back up at the stallion that was now within hoofs reach. "Ah liked the kiss but..." She paused and tried to think of why she couldn't like the kiss and the way she felt when he had done it. She glanced up and saw a look of pure concern on Elusive's face.

She swallowed and spoke with a shaky voice. "Ah just don't know. We've been friends for years now but Ah just don't know if this can work."

Elusive stood there for a moment before his ears fell. "Oh... I see. You're right. This was foolish of me."

The stallion turned away and walked back to the small table with the drawings and sat down. He felt as if his heart had been punched through. Where is this coming from? It's just a simple bet and even if I don't win there's always the chance that Berry will. So why does her rejection hurt?

He sighed and glanced back at the mare in the wonderful dress. "Of course this couldn't work. Between your farm work and my fashion line we hardly get to see each other as it is but setting aside time for something romantic like a date or even something like this would cause some sort of backlash eventually."

He looked back at his designs for a moment. "I would take up too much of your time anyways and you farm must come first. Perhaps it is best we just stay—"

A strong hoof grabbed him by the jaw and spun him around. Next thing he knew his lips were locked with Applejack's. He sat there stunned for only a moment then wrapped his legs around the wonderful mare’s neck. The kiss ended much too soon for the stallion but the look in the mares eyes was set.

"Ah don't want to hear nothin' like that from you again. We'll figure somethin' out but for today it's just you and me fancy boy, we may not be datin' yet but that don't mean we can't have some fun together today. Ah do recall you sayin' somethin' about takin' me out for lunch."

Elusive could only smile at this radiant mare as he held her. He gave her a sly smile as he spoke. "Of course, let's get you out of that dress first."

Applejack punched him lightly on the shoulder. "Ah ain't that kind of mare." She gave him her own playful smile. "But Ah might make an exception for you."

Elusive and Applejack found themselves at a small, outdoor restaurant eating and talking happily. Neither of them had realized how much they truly had in common. Both of them practically raised their younger siblings, they both ran complicated and, at times, incredibly stressful jobs, and they both loved to read in their spare time.

"Ah reckon that if we had spent a few minutes just talking instead of yellin' we might have done something like this a long time ago."

Elusive chuckled. "I think you're right. This day has been wonderful. But alas after this I think you might be heading back to the farm. I'm certain that Macintosh and Apple Bloom might need you for something."

Applejack leaned back in her seat a little. "Well they might have to wait. Ah have no intention of leavin' just yet. You just started getting interesting."

They both laughed and continued to talk about anything and everything. As they talked Elusive found that he was beginning to care less and less about the bet and more about the wonderful mare in front of him. He felt more comfortable around her than he had in years. He didn't care that he might lose the bet, or that he may have to pay up to either of his male friends. At the moment the only thing on his mind was the fun and conversation he was having.

I really should have asked her to do something like this a long time ago.

Applejack cleared her throat after a while and gave Elusive a small worried look. "What about Spines?"

Elusive's eye brow rose. "What about... oh..."

Elusive felt his smile fade as he thought about the small purple dragon that had developed a crush on him. His fell into a deep frown once he realized that by spending time with Applejack, and ultimately dating her would break the small dragon’s heart.

Elusive sighed. "This is going to be rather unpleasant isn't it?"

Applejack could only nod. "Do ya want me to break the news to her?"

The stallion shook his head. "No. I'd think it'd be best if I did it. Better to have her angry at me than at you."

"When will ya break it to her?"

Elusive took a sip of his water and look thoughtful for a moment. "After this Saturday. Berry and Fluttershy have a date and I had planned to help Berry with ideas for it."

Applejack nodded. The pair moved on to much less worrying topics, paid for their meal and walked along the streets of Ponyville without a care in the world.

Elusive found himself inside the bedroom of his friend Bubble Berry and trying his hardest not to scream in terror. The room was covered in bright pink wall paper, confetti, party streamers, and balloons of every color. All of them the very stuff of nightmares for a fashion pony. He focused his attention on the small alligator that was sitting next to him on the bed. His mind was drifting off to the day he had experienced so far with Applejack and the wonderful kisses they had shared.

Berry was talking, unaware that his friend was only barely aware of him doing so. The pink stallion was bouncing around the room with a dreamy smile on his face. "And then she said yes! I can't believe she said yes! I think she might like me just like I like her!"

Berry stopped bouncing for a moment and looked over at Elusive. "Sooo?"

Elusive came back to reality and looked at the expecting eyes of the stallion. "Soo... what?"

The pink stallion gave a small snort and waved his hooves in the air. "DUH! You and Applejack! I saw you two talking a lot today and I was wondering how it went! Did you ask her out or were you two already on a date?"

Elusive smiled a little at his friends rather animated actions. "We did share the day with one another but I think that for now we can say that it really wasn't a date. Not yet at least. We both still have some small reservations. At the moment we are in limbo. Our jobs do take a lot of time and effort to maintain."

The white stallion waved his hoof passively. "That doesn't matter at the moment. What does matter is you and Fluttershy. She told me that you have had feelings for her since you both met. Is that true or are you just saying that to win the bet."

Berry frowned at the accusation. "I would never lie to her like that. I really do like her and I have since we met. She's the prettiest mare I've ever even seen." He stopped for a moment as his ears drooped. "You think I would do something like that?"

Elusive shook his head and gave the pink pony a small reassuring smile. "Oh course not. I was just worried about Fluttershy's feelings. I can see that my worries were misplaced and I do apologize for doubting your character."

Berry's ears perked back up and he beamed at his friend. "Well of course you would be worried about your friend. She is your spa buddy."

Elusive nodded then gave the baker a more serious look. "However this does bring up a question. If you felt this way about her all this time why did you wait until now to ask her?"

Berry's ears dropped back down and his gaze fell to the floor. "I... I wasn't brave enough. Every time I tried I kept getting scared that she would say no or reject me. When you and Blitz started talking about the bet I joined in so—"

"—So we would force you to at least try." Elusive finished for him. "In case you got cold hooves we would be there behind you to help you. That's rather brilliant but still, if you needed help you should have come to one of us. We all could have helped you out. I could have set you and her up at the spa so you two could have some time alone in a quiet place."

The pink pony stayed silent for a moment then spoke in a heavily embarrassed voice. "I didn't want you all to think less of me. I mean what kind of stallion is scared of talking to a mare."

Elusive got off the bed and walked next to his friend. "None of us would think less of you. It's natural for a stallion or mare to be afraid of rejection. Besides didn't your grandmother tell you to laugh at the things that scare you?"

Berry looked at his friend as if he was crazy. "You want me to laugh at Fluttershy? Isn't that kinda mean?"

Elusive facehoofed and sighed. "No. What I meant was that you have always had the ability to talk to her and face your fears but you needed some confidence first. Now let's focus on something much more fun, your and Fluttershy's date in a few days."

The pink stallion smiled widely at the thought. He nodded and sat down on the bed as Elusive began to tell him things that Fluttershy might like to do. His mind wasn't in the room however as he imagined himself sitting with Fluttershy and just holding her close to him.

Two days had crawled by for Bubble Berry but at the moment he thought that the wait was more than worth it. The sun was shining brightly on the small path he was walking on as a gentle breeze blew along. It was the perfect balance of warmth and coolness to keep the day from becoming uncomfortable, which was great for Berry because he was going on a simple picnic. He held the basket and blanket upon his back as he whistled a merry little tune.

He stopped on the path when he spotted the familiar cottage. Sitting beside the cottage at work on her garden was the mare of his affections. The pink maned mare glanced up when she heard him whistling and spotted him staring at her. They both blushed and glanced away from each other in embarrassment.

Berry walked up to her as she blushed behind her curtain like mane. "Uh... hi. I brought some stuff for a picnic. I hope you don't mind."

Fluttershy looked out from her mane with one of her large, beautiful eyes. She was still finding it hard to believe that this kind and happy stallion and herself were now about to go on their first date. Her first date. "Th-that sounds lovely. Where did you have in mind for us to go?"

The pink stallion smiled at her kindly and pointed off to the side. "I know of this great little spot near the meadow. It's really quiet and nopony really goes there much."

Fluttershy swallowed and smiled back at her friend. "Lead the way."

They set off down the path for a little while then turned of onto the large field beside the path. They walked in silence for the most part until Berry pointed at what looked like a small pair of trees standing together.

"There it is. I'll set the blanket down for us."

While Berry set the blanket down for them Fluttershy inspected the pair of trees. She soon discovered that they shared the same trunk that split into the separate trunks she had seen. She took a few steps closer and realized that is wasn't on tree with two separate trunks but two trees that had grown in the same spot and were inseparable due to this growth.

Fluttershy turned to the stallion as he laid out a few plates for them. "How did you find this spot?"

Berry looked up at her and gave her a sheepish grin. "Actually a friend told me about it. Said that they used to come here all the time."

Fluttershy looked back at the tangled trees. "It’s lovely."

Berry walked up next to her and gazed at the tree. "So are you."

Fluttershy began to blush furiously and she hid behind her mane. She managed to get out a small squeak. "Thank you."

Berry smiled at her and nodded toward the blanket. "I brought some food and drinks for us. Would you like some?"

The mare only nodded as she lay down on the blanket. Berry pulled out a small loaf of bread, some jam, a mincemeat pie, and plate full of vegetables. He then produced a small group of thermices.

"I didn't know what you would like so I brought a few things. I have tea, cider, and some punch."

Fluttershy came out from behind her mane long enough to look at the three thermices. "Tea please."

Berry filled a small cup and placed it down in front of her. Berry filled his own with some of the punch and sat there silently. The moments stretched out and became almost painfully awkward as they looked everywhere but at each other. Berry gave a small cough and Fluttershy jumped a little.

She glanced at him for a second. "Did you say something?"

He shook his head and gave her a small smile. "No... just a cough."

Silence fell on them once more. Berry cleared his throat and looked directly at Fluttershy. "So... How have you been?"

Fluttershy moved her mane out of the way slowly and looked at the still smiling stallion. "I guess I've been fine. I was looking forward to this a lot. It really is a lovely spot."

Berry nodded. "Yeah. I have been looking forward to this a lot as well."

Fluttershy placed a small slice of bread on her plate and spread jam on it. Berry was already through his second piece of pie as the silence stretched on. Fluttershy watched him for a moment as he gazed up at a small group of clouds drifting through the sky. She hadn't really noticed the way his smile seemed to brighten his face and the energy that he seemed to give off. It made her feel safe and happy, just by being near him.

Berry glanced over and spotted her smiling at him. He smiled back and tried his hardest not to chuckle as she blushed and hid behind her mane. He scooted closer to her and nudged her gently.

"Hey come on, don't hide that smile. It's really pretty and should be seen by everypony."

Fluttershy felt his hoof moving her mane out of the way so he could look her in the eyes. "See? Much better."

Fluttershy returned the smile. "You think my smile is pretty?"

The pink stallion nodded. "Of course. You never smile enough for my liking but every time I see it I can't help but smile all the wider. It's like a balloon just swells up inside of me and it's filled with happiness or maybe that funny gas that makes your voice go all squeaky."

Fluttershy began to giggle as Berry tried to make his voice go really high. "I think this is the sound. Close enough?"

Fluttershy couldn't respond as she was laughing at the stallion’s voice. Berry joined her in the laughter and the pair soon found themselves just looking into each other’s eyes as they stopped laughing. Berry pointed to some of the pie after a few moments of them just silently looking at one another.

"There's still some pie left..." He glanced back and noticed that Fluttershy had moved next to him and she laid her head on his shoulder. The pair laid down on the blanket and watched the cloud roll gently across the sky, talking about baking, animals, and news that Elusive and Applejack might have be dating. Berry knew the true reason to why the pair had been seen together but remained silent on it.

Fluttershy snuggled close to him and spoke softly. "Do you think they might start dating, like us?"

Berry gave a small cough as he tried to think of an answer. "Well... I think they might try to date but I really can't say how it will go."

Fluttershy laid her head down on his chest and let out a small sigh. "If they do we could go on a double date."

Berry nodded and looked down at the mare. She closed her eyes and nuzzled his warm coat. Berry felt his heart swell for a moment and he hummed his approval. "Yeah. That would be nice."

The pink stallion closed his eyes and together the pair fell asleep under Celestia's sun.