//------------------------------//
// Hedging Your Bets 
// Story: Smitten 
// by Natedogg2006 
//------------------------------//

"Alright Twi, you got us here. What was the big important thing y'all needed to ask us about?"
Twilight had managed to gather her friends  to the most neutral place that was immediately available to them which was also at least reasonably private. Sugarcube Corner was suggested by more then one of them, however that idea had been flatly turned down by Twilight. Luckily Rarity had had some work to do, but not so much that she couldn't entertain. So it was with a sigh that Twilight sat down in one of the Carousel Boutiques many luxurious chaise lounges and looked around to her friends. Before she could begin however, Rainbow Dash decided to chime in.
"Wait a sec, aren't we still waiting for Pinkie Pie?" She had found a soft pile of discarded fabric and decided to make herself an impromptu nest while she had waited for the stragglers of the group to arrive.
"No actually. Pinkie will not be joining us today. Do to the fact that we are here to discuss something involving Pinkie," Twilight began to explain.
"Oh no," Rainbow groaned as she sat up in her makeshift bed. "Are we trying to throw her another surprise party? Because if so I am totally not going to be the one who goes to get her this time."
From nearby Rarity turned away from the ponyquin she was working off of to direct a look of concern to Twilight, even while she lit her horn to push pieces of fabric Rainbow was scattering around back into the pile. 
"That can't be it, her birthday has only just past a short time ago. Is there something wrong with Pinkie that you need our help with?"
"It's, umm. Well, it's definitely not a party. And it's not anything wrong necessarily. It's, a little more personal then that, and not something I really have much experience with."
What happened next was not anything close to what Twilight had expected when she had called this meeting together. Very suddenly both Rarity and Applejack looked somewhat down cast, Applejack going so far as to let out a groan. And though Fluttershy had been mostly quiet up until now, even she seemed to draw away, hiding behind her hair from her position in the corner of the room. At the same time Rainbow Dash seemed suddenly much more interested in the conversation, eagerly rising from her place and stepping over to Twilight.
"Oh yeah, and just what sort of personal thing might be going on between you and Pinkie that would have you so concerned?" Rainbow Dash seemed to be just barely containing smug excitement at news she hadn't even heard yet. 
Despite this taking Twilight aback somewhat, she did press on with her announcement. "Pinkie Pie... Kind of, asked me out on a date."
"Consarnit!"
"Oh bother!"
"Boom! Pay up chumps!"
Twilight watched stunned as Applejack grumpily removed her hat from her head and rummaged inside. At the same time Rarity lit her horn and floated over a set of saddle bags from the corner of the room. 
"....., You, you all seriously took bets on if Pinkie would ask me out?"
Rainbow, in her triumph, decided to answer. "It's kinda a small town Twi. Until you got here not a lot of interesting things happened." 
"Y'all can say that again," Applejack chimed in, removing a bit bag from her hat and beginning to go through that instead. "Dash once won forty bits offa' me on how many dead stumps she could pull outta' the ground in one day." With a smug smirk she now offered up a good sized hooffull of bits to Rainbow Dash along with an equal pile held in Rarity's magical aura. "Good thing she didn't realize until later she'd done a few hundred bits of labor in the process."
Rainbow Dash snatched Applejack's pile with a sneer. "I still won the bet," she spat out, tongue extending. 
"And I won a new west orchard," Applejack retorted, placing her hat back on her head and straightening it a little too smugly.
Twilight had watched this exchange with some bit of interest, but was still curious about how it related to her situation. "....., But seriously. You three actually took bets on my previously non-existent love life."
"Not three," Rainbow declared as she cast a sly grin to the corner of the room. 
Fluttershy now had a bright blush on her face as she nervously poked at Rarity's carpet with her hoof. "I didn't bring any bits with me, I didn't think I would need them. I promise I'll pay you back later." She finally squeaked out the words before even more pensively looking over to Twilight. "Sorry Twilight."
"It's... Ok, I guess." Twilight responded, thinking over what had been said so far. "I guess I really don't mind you girls making friendly wagers about me with each other from time to time. I suppose. And I guess I can even see why most of you wouldn't think Pinkie would ask me out. All of you know I really don't have any romantic experience to speak of after all. I just don't see how the idea of Pinkie asking me out would have ever even come up in order for there to be a bet in the first place."
"We all thought Pinkie would ask you out," Dash commented casually as she absentmindedly counted through her fair sized pile of bits.
Twilight was confused again, her mind racing to try to put together threads of logic from all the new information she was getting. "But then... Why?" She asked while motioning to Rainbow's pile of bits. 
"Oh it's nothing darling," Rarity decided to answer as she put her saddlebags back in their place and again began walking around her latest creation. "Our dear Pinkie is just somewhat of the romantic type."
"I'd say she's more of a smitten kitten." Applejack cut in, once again readjusting her hat now that it was an unknown number of bits lighter. "She gets crushes like a carpenter gets splinters. I think she's been on at least one date with nearly every unhitched pony in Ponyville." 
Twilight was once again shocked by this news. She looked around the room, seeing looks of confirmation among the surrounding group. "Really? She's been on that many dates?" Her voice trailed off somewhat as she spoke, apprehension settling in as she attempted to keep it masked.
Rainbow Dash, having stashed away her earnings, decided to chime in again. "Yeah. I mean, why do you think I was a little hesitant to hang out with Pinkie alone after we all became friends. I thought for a little while she was trying to find a reason to get back together with me."
"You dated her too?" Twilight asked, noticably shocked.
"I think I was one of her most recent relationships actually. We broke up probably less then a year ago. Just a little before you showed up. She hasn't been dating nearly as much as she use to, but most ponies just figure that's because she's running low on new ponies to date. That's why we all figured you'd be getting asked eventually. I was just the one who guessed it the closest," Rainbow said with a sly smile.
"So you two dated, but then broke up?" Twilight considered this for a moment before speaking again. "If you don't mind me asking, why did you two break up?"
"I don't know." Rainbow Dash absentmindedly said as she made her way back over to her previous napping spot and tried to settle back in. "We had some fun together, but thinking about it afterwards I kinda think it didn't work because we're really too much alike."
"If that ain't the understatement of the century."
Rainbow Dash gave Applejack an incredulous look that made Applejack scowl back. "I don't know what you're talking about" She said with as much sarcasm as possible before turning over where she lay so nopony could see her smirk.
"I agree with Applejack, the time the two of you were together was quite the trial on the patience of most ponies in town. Your recent pranking activities have been trying as well, but nothing like back then." Rarity said this with a huff, somehow expressing a lot of deep seeded frustration in the one gesture.
"Yeah. I don't know what it was when we were dating, but we just kept trying to go bigger and bigger. Made things a little too much of an effort to want to keep going. Kinda just had to stop after a while." The last part came out softer, almost wistful as she continued. "That's why I decided if I randomly did start dating again, I'm probably going for somepony from the exact opposite end of the spectrum. Balance things out a little ya' know."
Fluttershy suddenly looked over to Rainbow Dash from the place where she'd been sitting quietly. "But, I thought you said you weren't going to date anypony ever again?"
Twilight was suddenly concerned by this news. "Ever again? Did you and Pinkie have a major falling out over your relationship or something?"
Rainbow Dash rubbed her foreleg across the back of her head hesitantly as she stood back up. "It, it got a little rocky when we cut things off, but it probably just seemed worse at the time. And honestly Shy," she turned to her fellow pegasus, "you probably had to deal with more then your fair share of it. I ended up venting a little too much about it to you. Thanks for that by the way."
Fluttershy looked away, hiding her face with her mane. "It's ok Rainbow, I'm happy to help you with whatever you need."
"You're a pal, Shy." She sent her friend a smile. 
"Ugh," Twilight suddenly exclaimed in frustration. "This is just what I was afraid of though. This is why I didn't give Pinkie an answer."
Rarity suddenly paused in what she was doing, which for some reason unknown to Twilight did not involve her current dress and instead involved her looking back and forth between Fluttershy and Rainbow Dash. She now looked over to Twilight and gave a slightly dramatic gasp. "You didn't give poor Pinkie an answer? Why ever did you do that deary?"
"Because I wasn't sure. I wasn't sure of like, most things about it." Twilight felt herself becoming frantic. She stood from her seat and began to pace as she tried briefly to calm herself, but the rest of her words just started flowing from her. "I've never had a special somepony before. I've never even thought about it. And now I have to think about it. And I also have to think about how it affects us as friends. I have to think about it in terms of us both being elements of harmony. And part of both of those is what happens if it doesn't work out and how badly it might not work out. And now I also have to think about it in terms of Pinkie having been on way more dates then me and exactly what that means." She finally managed to catch herself, pausing briefly to take a deep breath. Her voice dropped into something almost melancholic as she continued. "And... well, I still have to think of it in terms of myself, and what it means for me."
Every other pony in the room stopped to consider Twilight's rant for a few moments, glancing around to each other in the process. Applejack was the first to respond. "Lots of insecurities to unpack there, and I reckon' this is what y'all gathered us here for in the first place." Twilight nodded. "So let's just go through them one at a time sugarcube." She gave Twilight a warm smile, one she managed to give back.
"First of all, if I'm completely honest, what happened between me and Pinkie might have kinda, maybe... been slightly more my fault then hers. It's probably not something you really need to worry about happening with you," Rainbow said, looking a little embarrassed.
Twilight turned to Rainbow Dash, some confusion showing in her expression. "But if it ended badly for you, it could end badly for me as well. I don't want things to end up awkward between me and Pinkie."
"Twilight, you might be a neurotic mess who can go completely off the deep end because of some trivial stuff, no offense."
"None taken."
"But overall you're actually waaaaay more mellow then me."
"In deed. If you haven't noticed our dear Rainbow can be a bit of a hot head from time to time."
In an obvious mock show of anger, Rainbow once again stood from her makeshift napping place and stomped towards Rarity. "Who you calling a hot head," she growled.
Rarity rolled her eyes but otherwise ignored the display. "I didn't witness it personally, but I did hear their breakup did involve a rather public blow up. But honestly we've already said that Pinkie has dated most of the town. One bad breakup among probably over a hundred is something I think a pony like you would call, 'statistically insignificant', I believe."
Twilight considered that for a few moments. "Yeah, I guess that's true. I've never heard of Pinkie's dating experience before, but I do know she's friends with everypony in town. If she's still friends with all of them I guess it doesn't end badly most of the time."
"In deed darling. My personal experience was one of a rather surprisingly enjoyable night out of dinner and dancing. She even walked me to my door like a perfect gentlemare."
"Wait, you dated her too?" Twilight asked, interrupting the story.
"Yes darling, as we said she's dated nearly the whole town to some degree. Though I wouldn't really say we dated. It was one date, and she understood when I turned her down for a second."
Once again Twilight had to consider before asking. "Why didn't you go on another date with her?"
"Priorities obviously Twilight." Rarity said this while once again turning to the dress she was working on. "Pinkie and I have vastly different goals in life. She has some idea of how to treat a mare, but it couldn't have lasted forever and we both knew that. Better to end on a high note is it not?"
Twilight considered this for a time. Her tension seemed to be visibly reducing as she did. She finally relaxed enough to sit herself down on the floor and address the rest of the group collectively. "That actually makes me feel a lot better about this whole thing already. I was getting a lot more stressed about this for a second after finding out all these new details. I... I was originally leaning towards going out with her actually, but for reasons that I wasn't sure were good reasons for going out with somepony."
Attention was definitely back on her as her friends looks to her turned curious. Rarity's work stopped again as she was the first to address this. "Oh really now. So there was a chance you did want to go out with her. What might I ask made you want to take her up on her offer?"
Twilight felt herself blush, but she knew it was only due to the attention now being paid to her. She proceeded nonetheless. "Well I, I don't think I really actually wanted to. At least I don't think I did. I've honestly never thought of another pony in that way, much less about a mare. But at the time it was the only thing that came to mind that seemed to make sense. Flat out rejecting her would have been way too mean, and I couldn't do that to her. I thought I probably should say no, but no matter how hard I tried I couldn't think of any way to turn her down gently." Twilight stopped for a moment as she noticed glances passing between the other mares in the room. "What?"
"Oh nothing darling, please continue."
Twilight looked between the assembled mares, but did continue. "When I told her I'd think about my answer I was leaning towards a yes, but only because I figured nothing would happen and we could just be friends like it never happened afterwards. Hearing what happened with Rainbow Dash made me think that was a really bad idea though, which made all my other reasons for why I should, and shouldn't, go out with her way more complicated." More glances started passing between her friends. "What?"
"Stop being paranoid Twilight. So which way are you leaning now and why?" Rainbow blurted this out quickly, for some reason drawing a glare from Rarity. 
Even more confused at their behavior she thought it would be best just to try and see where they were taking this. "I'm... still leaning towards going on at least one date with her. I've never thought about a romantic relationship before, but I never discounted the possiblity. And... With this new information I was thinking that maybe Pinkie would be a good choice. She obviously has a lot more experience at this sort of thing then I do, so maybe she could help me gain some experience without, you know, too many complications." Hearing the words come from her mouth she suddenly cringed. "Is that a horrible reason to go out with somepony? It's almost like saying I want to go out with her so I can go out with a better pony later." 
This question seemed to throw off whatever path the others were trying to lead her down as they seemed to become serious again at her hesitation. However, to Twilight's surprise Fluttershy now chimed in. 
"I don't think it is. Pinkie is a really nice pony and really likes helping other ponies with anything. When she asked me out I didn't think it was a good idea because she was so much more experienced then I was. But she said we could just go out on a few dates and see if I did like going on dates with her."
Less surprised this time, Twilight now considered this new information much the same way she had with her other friends. "You too, guess that makes sense. Did you actually go out with her?"
"Well I, I probably wasn't going to at first. I don't think I could ever really think of Pinkie in that way. But she seemed like she would be ok if I just tried out dating with her... And well," she paused a bit longer as Twilight noticed color come to her cheeks. "I thought I...I might want to know what it's like to go on a date, just, you know, if it happened someday for real. Not that I really thought it would or that there was even anypony I thought I'd go out with or anything like that, or..."
As Fluttershy's explanation became more and more stuttering panic, Rarity stepped over to cut her off with a reassuring hoof on the shoulder. "I think what the poor dear is trying to say is that Pinkie's casual nature to relationships, and most other things, makes her an ideal pony to have your first date with if you do decide to go that route. Isn't that right Fluttershy?"
Fluttershy nodded timidly, but Twilight still wanted a little more information. "If that's the case, then how did it end between you two?"
Fluttershy had calmed for the most part so she just smiled as she continued. "Oh, that was actually fairly easy. When she asked if I wanted to go on a fourth date I just told her that I thought she had helped me enough. She told me she was glad she could help and that was it." 
"Really? It was that easy?" 
Fluttershy nodded. "Pinkie is a really good pony. As random as she is she can be very understanding."
Thinking again for a minute Twilight decided to turn to Applejack. "What about you?"
"Me what?"
"Do you have any tips about dating Pinkie that might help me make a decision?"
"I never dated Pinkie, sugarcube," Applejack replied casually. 
"She never asked you out?" At this point in the conversation that was now a shocking thing to hear. 
Applejack just rolled her eyes and shook her head. "Oh she did, but my barn door don't swing that way." Twilight felt her cheeks heat up as the realization of her assumption hit her. "Yeah, told her if she wanted a datable farmpony type she could always try Big Mac. Don't think she ever did though."
Twilight cringed just slightly at that. "Well that kinda leads to what I think is the last issue I was dealing with I guess."
Her friends, specifically Rarity, Rainbow and Applejack suddenly seemed oddly interested in what she was saying again. 
"That part about not knowing what it meant for you. Is that what you mean darling?" Twilight nodded. "Exactly what is the problem there?"
Twilight blushed again. "I said I never discounted the idea I'd ever have romantic feelings for somepony. I don't think I ever have, but I just figured if I ever did it would be, you know, with a stallion."
"So now you're just wondering if you could actually have the hots for a mare huh?" Rainbow said, waggling her eyebrows and swaying her hips as she stepped towards Twilight. "We could test that one real easy right now Twilight."
Twilight's face went very red very quickly and she found herself shuffling across Rarity's carpet in the distinct direction of away from Rainbow Dash. A hoof on her shoulder from behind stopped her and she turned to see Rarity smiling to her reassuringly. "Yes, it is easy to test. But I can assure you it does not need to involve anything untoward like Rainbow might be thinking."
Twilight turned with a glare as she heard laughing, finding Applejack and Rainbow exchanging a  hoofbump. Rarity turned Twilight back to face her, finding Fluttershy over with her as well.
"It's ok Twilight, Rainbow is just teasing a little. I'm sure she didn't mean to scare you," the yellow pegasus said while directing a scowl behind Twilight at the continued laughter. 
"Fluttershy is right dear. Her forwardness is definitely not something to take as the only way to approach this situation. What I want you to do right now is to close your eyes." Twilight was hesitant, backing away a little at the suggestion. "Don't worry darling, we wouldn't try anything. I'm more interested in stallions lately and I think Fluttershy has another pony in mind." Both Twilight's and Fluttershy's gazes snapped to her. She continued without explanation. "We just need you to focus."
Twilight hesitated again, but did decide to close her eyes. From behind her she heard Rainbow speak up again. "Hey Rarity, I think this qualifies as..."
"It does not, now quiet you." Twilight then heard Rarity whisper something to Fluttershy. Thus was it the voice of the soft spoken pegasus that she heard next. 
"Ok Twilight. First what I want you to do is relax. Try to quiet your mind and take a deep breath." Twilight did take a breath, but was finding it somewhat hard to quiet her mind. She heard Fluttershy make an uncertain noise at this. "Ok, let's try this. Try to remember the way you feel on a nice warm day in your library. Laying on a nice fluffy pillow. Maybe reading that one book you've been trying to find the time for for a while."
This actually did allow Twilight to relax some, Fluttershy's smooth voice assisting somewhat. It must have been noticable because she heard whispering again and Fluttershy changed tactics.
"Ok. Now I want you to think about Pinkie Pie. Just regular old Pinkie Pie the way you see her every day."
With little effort the image of the pink pony that had been sitting on her front step asking her out just earlier that day came to her mind. Eyes closed and smiling brightly as she bobbed back and forth, her flanks plopped down as she danced to the unknown music only she ever seemed to hear. She didn't notice the corners of her lips start to rise ever so slightly. She did notice more whispering from Rarity as well as the sound of fabric rustling.
"Ok. Now I want you to think about who Pinkie is. All the things that make her your friend." Again, that was easy enough for Twilight to do. Images flashed through her mind of various adventures they'd had together and all the things she did all around town for ponies. "Now I want you to think about those things in terms of if they make a pony attractive. And when you're done with that, I then want you to think of your image of Pinkie again."
This was a little harder. Twilight had put little thought into what she might want from a romantic partner. But thinking about it now she did feel like Pinkie could be attractive to her. The way she could make ponies smile was an amazing trait. And seeing her smile when she made others smile was amazing too. Did her smile always seem that... Cute?
And Pinkie was an eternal mystery to Twilight. She'd accepted long ago that figuring out what made Pinkie tick might be a lost cause. Maybe getting to know Pinkie in... different ways, might give her a chance to study the unsolvable conundrum that was the random party pony. And why was doing research sounding even more appealing then it normally did to her right now?
And then there was Pinkie's endless energy. And it was almost always positive energy. Twilight could imagine that if she ever wanted to just stay up all night talking to somepony, Pinkie would volunteer in a heart beat. And considering how many nights she stayed up, Twilight thought having somepony other then Owlowiscious to talk to might be nice. 
And suddenly Twilight realized that her mental image of Pinkie had changed. Twilight couldn't quite figure out how or why she was now picturing the ponies curvy form, when did she get that curvy???, from behind. Or why the theoretical Pinkie was giving her such a big smile while looking back towards her from across her own body. And why was she fluttering her eyelashes like that?
Twilight was a little too focused on how off the rails her own thought process had gotten to notice her slightly more rapid breathing or her very warm face. What she did notice was Rarity now taking a turn talking to her.
"Ok deary. Now I want you to open your eyes and picture her wearing this."
Twilight, without thinking about it, did open her eyes. Apparently Rarity had been busy while her eyes were closed. The ponyquine she had been using before had been swapped for one wearing something that definitely wasn't her usual type of design. Twilight had seen lingerie before, but never actually on any kind of pony form. And before she could stop herself those two images now in her head did manage to superimpose themselves over one another. 
Previously Twilight could only speculate on the purpose of clothes such as the light blue, sheer, frilly, and barely there garment now barely covering the hypothetical Pinkie Pie in her mind. It always seemed odd seeing that most ponies didn't wear clothes normally anyway. But thinking about it now she realized the way they were designed to draw the eye to... certain places, while also keeping those places a mystery. It was enough for her to suddenly feel her eyes bulge, her jaw go slack, and her face to suddenly feel it had been set on fire. 
"..... Gay."
"Totally gay."
"Absolutely gay."
".....bi?"
"Just pay the lady Applejack."
When Twilight's mind finally managed to tear itself away from her thoughts her eyes refocused on her friends. Rainbow Dash and Applejack seemed to be in the middle of passing bits to both Rarity and Fluttershy. In the process Fluttershy was separating a smaller pile from her own winnings and passing them back to Rainbow Dash. 
Twilight watched the exchange, bemused. "Really, you took bets on that too? Are there any other bets centered around me I should know about?"
"Not unless you'd like to invalidate them darling." Rarity said this with no shame as she lit her horn, stashing away her new winnings as well as hovering over a bag from next to her Twilight hadn't noticed. "Something special for the special day. Free of charge, so just go have a good time."
Twilight looked into the bag and realized Rarity had indeed been busy while her eyes were closed. All of her friends gave her warm smiles, some bordering on sly. 
"Go get her sugarcube."
"Have loooooots of fun Twi."
"Good luck."
Twilight returned the smiles before turning to exit the shop. 
"One second before you go Twilight dear." Twilight turned back to where Rarity had called her. She turned to suddenly find a hoofkerchief thrust into her face just below her muzzle. Only at that point did she noticed the accumulation of moisture that had recently ended up there as Rarity wiped it away.
Twilight stared incredulously. "Ok, so I'm probably gay. You already won that one." Twilight rolled her eyes at the assortment of giggling that followed. She turned again to leave. 
Outside she stopped to take a breath and refocus. "Ok," she said to herself. "I know what I  have to do, so now I just gotta go do it."


***
Elsewhere in Ponyville


Pinkie Pie sat low on the carpet of her room above Sugarcube Corners. The reason for this seemed to be so that she sat within the eye line of her stoic pet alligator. 
"So what do you think Gummy? I didn't go too far did I?" 
She sat there, head low but her tail in the air, swaying in anticipation of his answer. Her smile was not her usual over the top one. It seemed to plead for an answer from the largely unresponsive reptile. She held the gaze for some time. Seemingly randomly, Gummy snapped his previously open jaws shut.
Seeing this, Pinkie shot up with a bounce. "You're right Gummy," she exclaimed, her voice seeming more determined. "I did everything right and everything is going to work out." Her voice dropped slightly as she continued, her smile dropping just a little as well. "...This time."
That moment ended abruptly as the singsong voice of Mrs. Cake came calling from back down in the restaurant. "Pinkie dear. Your break is almost over if you wanted to finish up what you were doing up there."
Pinkie took a deep breath as her smile restored itself to it's usual magnitude. "Sure thing Mrs. Cake, I'll be down in a sec."
"Oh, and one of your friends is here to see you too."
"Really?" Pinkie exclaimed, excited at this news. She quickly threw her apron back on and proceeded to prance back down the stairs. Her prancing was cut short when she came face to face with a purple unicorn at the bottom of the stairs. 
Twilight smiled to her sheepishly as Pinkie tried to keep her smile at it's usual level. "Oh hey Twilight," she said as naturally as possible. "What brings you here?"
Twilight opened her mouth to speak, but no words seemed to come out. She proceeded to clear her throat and try again. A dry mouth mumbling of "umms" and "ehes" was all that she could manage. 
Pinkie made herself smile even bigger. "Could I get you a hot chocolate to help you with your throat maybe," she said, tacking on a soft giggle as well. 
Twilight cleared her throat once again. "No no, I can do this. I've been practicing this the whole way here." She looked like she was going to start again, but didn't. Instead she seemed to say more to herself, "actually I think it'll be better this way." She turned her head and began to nose her way through saddle bags around her haunches. 
Pinkie watched with interest as Twilight finally turned back to her. She felt her smile threatening to drop when she saw a bouquet of flowers being held in Twilight's mouth. That threat subsided and her eyes grew wider when she realized they were actually different then the ones Pinkie had given her librarian friend earlier that day.
Twilight smiled brightly as she placed the flowers at Pinkie's hooves. "I'm free all day Saturday if you are."
Pinkie couldn't stop the smile from growing as her eyes shimmered with delight. "That sounds great."