Three months ago...

Greetings dear reader! Iron Will speaking. Have you ever had a crush on somepony? Have you ever ended up as a 'platonic friend'? Have you tried to prove to that special somepony how good of a guy you really were and she seems to date other guys who only seem to hurt her even worse? Or maybe you ended up with your special somepony/crush and you know nothing about the mechanics of an actual date.

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P.O.V.: Soarin

Okay, I know that that's a lot of money to part with, but I REALLY GOTTA GET THAT DAMN BOOK!!!

Present Day...

At this point, I really don't know why I had that flashback. The only thing that I can see as clear as day right now is that Rainbow Dash's muzzle is practically buried into mine. I gotta give it to her, for a mare with such a spunky personality and a sharp-ass tongue, her lips sure are soft.

"GAH!"

Immediately, I responded with a yelp of my own. "WAAH!"

In an instant, I pulled away from her as she jumped back a full five feet. Any more force in that jump and she might've been airborne. I try to reason with everypony in the vicinity.

"WHAT THE FUCK WAS THAT!" I hollered out to the cloudless sky.

I turn my attention back to the cyan mare that kissed me, only to see her profusely apologizing to her timid friend.

"Fluttershy, I... it... it was an accident!"

"So... you like him too?"

Oh shit. So not only does the beautiful mare that ended up saving my ass from an army of hungry, brown grizzly bears likes me, but so does her friend, who just so happens to be a recruit.

What a lovely combination of a drama. The shit just can't write itself any better than this.

Rainbow Dash just stared at the ground as the beautiful Fluttershy managed quietly hide inside of her mane. I'm not gonna lie, but she looks too damn cute when she's hiding behind a curtain of pink, flowing hair. The yellow pegasus was the first to speak to her shameful friend.

"Rainbow Dash, I didn't know that you were interested in Mr. Soarin."

And now I suddenly feel twice as old.

"Fluttershy, I don't like him! NOT ONE BIT! I DON'T LIKE HIM AT ALL!" The blue pegasus shouted, almost loud enough for the world to hear it. If she was trying to sell her performance, the yellow mare was definitely buying.

"But you kissed him."

Rainbow was looking all over the sky for a reason to come crashing down in front of her as she stuttered. "I... erm... uh... lost a bet?"

Seems legit.

"Oh. Well I guess that's okay. But why a kiss?"

Yeah, that's what I would like to know. How the hell does a kiss come into our wager? I don't remember anything about that at all. But then again, why get into the technical when this is all just one gigantic fib? Oh well, time we find out.

"Well," Rainbow started. "I wanted to give myself some motivation on beating him. If I had beaten him, then I would have him do the rest of my weather-related duties for the next week."

Excuse me, but I'm not here for you to be slacking around. So you can... just an excuse Soarin. Nothing more.

"And if I had lost," The rainbow-maned pegasus continued. "then I would have to kiss him. I guess my personal desire to not kiss him was too little in comparison to his speed."

Okay, even I'm convinced.

"Oh... Well I suppose that it would be fair that you'd follow through on your word." Fluttershy answered quietly.

Honestly, I can't believe she just bought that. I would've been skeptical to the point where I'd pretty much automatically assume that she kissed me for the hell of it. Not saying she didn't, but it is what it is. Oh well, at least she covered for me and now I can still get a date with Fluttershy.

This is a pretty damn good win. Now all I need to do is report back to Canterlot with my punishment served and I can leave this boring old town.

"Yeah! Why would I even have an interest in somepony who's my superior? It's awkward when I have to salute him in public and be all mushy-mushy in private."

I wouldn't be surprised that she'd be the main one to have those kinds of feelings. The best thing for me to do is leave this place and not say a word on what's happened here. Now if only I can get my legs to work.

"Mister Soarin?"

And that damn voice is like butter to my ears as I become swept like a bee to the overbearing scent of a flower's nectar. "Yes?"

"I... well... how long would you be staying here in Ponyville?"

Okay, I'll bite. "Why do you ask?"

"Well... I... was kinda wanting to know... if... you... me... well... would... uh.... oh dear."

Why do I have a thing for shy mares?

"I think what she's trying to ask for," Rainbow steps in. "is for you to spend some time with her."

"Oh not just me! I would really like for him to spend time with all of us."

And a certain song comes to mind. If you wanna be my lover, you gotta get with my friends...

"All of us? Why all of us?"

"Well, I just want to be fair to you and the other girls. Plus, if I go out with all of you and him, I can see if you all would approve of him."

And now I get a little nervous. Luckily, my saving grace was with Rainbow Dash dragging her off further down the street. I can't complain. This is an exit out of an extremely awkward question. As I watch them leave, I couldn't help but to notice the swaying motions of the yellow mares tail.

In all honesty, I'm hoping she accidentally gets spooked by something so I can at least catch a glimpse of what I'm going for.

I'm so going to rut that six feet under.

P.O.V.: Rainbow Dash

I can't believe that Fluttershy just asked him to an outing after I kissed him. I can't believe I kissed Soarin! So I guess all that lip service he normally gives during the drills makes for some pretty soft cushion.

WAIT! WHAT AM I EVEN THINKING ABOUT!? Let's focus back to what's going on here.

"Um... Dashie?"

Need to get back on topic. "Why in the hay are you asking Soarin for a group date?"

Fluttershy blushes as she does her usual prodding of her hoof into the dirt whenever she gets nervous as she answers my question. "I just wanted to see if you girls would approve of him."

"You don't need our approval!" I scolded her. "If you want to be with Soarin, then that's your business. You don't always have to drag us along when things aren't exactly comfortable."

I may have been a little too harsh. Flutters is already starting to withdraw from me, and she hasn't even physically shown it yet. Despite her standing still, she's backpedaling even as we speak. I changed my approach to a more gentle one.

Gentle isn't exactly my style, but I managed to become tender when dealing with her, and Scoots too.

"Look, I'm not saying don't go on a date because we're not going. In fact, I want you to go on a date with him. I don't need to you to not go! Go with the guy!"

Fluttershy's starting to warm back up now. She asks me without a moment's hesitation. "But do you think it's for the best?"

"Fluttershy, I'm not going on a date anytime soon. Applejack's got a date on the front line, Twilight, Pinkie and Rarity will go with whoever they want to. What I would say you do is go with him first. Then when you decide you like him for yourself, then you can come to us about whether he's a good fit."

Applejack must be wearing off on me. I'm not usually good with giving good advice outside of flying. Oh well, I just hope what I said was good enough.

"...Thanks Rainbow Dash." She answered quietly, sucking me into her hooves for a hug. Admittedly, she was always good at hugs. Better than I could ever be. That's probably why she's got a better chance with him than I do.

FOCUS DASH! This is about her and not you.

"Anytime. Now go out there and ask him for your date."

"You're right!" Fluttershy responded, seeming even more confident than ever. Maybe I don't need to baby her into asking him after all. "I will ask him for a date. And I will be more than prepared to see through to spending some more time with him."

Fluttershy gallops off as I smile back to her, subconsciously thinking about her words 'spend some more time with him.' Honestly, I felt jealous of her. Here I was, the first one to go on a date with him and he doesn't even give me a second go, and with Fluttershy, he's practically head-over-hooves with her. Was it just me?

I didn't get a chance to answer that question as Fluttershy slowly flies back over to me with a timid smile on her face. "Um... Maybe it's best if you come with me to talk me into it?"

Oh for the love of-

P.O.V.: Soarin

Got my tickets, got my bags, got my uniform and my keys. Welp, the only thing I need to do is check if my balls haven't frozen off from the snow and I'm golden.

"Mister Soarin!"

Shit. Here we go again. Damn that siren-like soothing element to that filly's voice. "Nnnnyes?"

Wow, I sound like a total creeper.

"Flutters wanted to know if you would be interested in spending some time with her this weekend?" Dash asked, using a wing to scoot her silent friend closer to me. Though her haunches drag in the dirt for a short while, she giggles nervously as she looks at me.

"I would normally check on the squirrels that day since I don't really go out and do much. But if you're willing to stick around, then I would be more than happy to reschedule my time with them."

Squirrels? That's how you spend your Saturdays? Feeding some random squirrels some nuts? Boy, I gotta introduce you to the boys down below because your sex life must reall- HOOF IN IT, SOARIN! You can defile her innocence after we get off of first base.

"Sure! I'd be more than happy to stick around. What time do you want to meet up?"

Her motions are heart-attack-inducing at worst. Curling herself behind the feathery veil of her wings as she hides herself from me. Captain Obvious states that the nervous, shy mare is nervous and shy. But she's incredibly cute. I can't just simply have my way with her, I need to warm her up and then we can talk dirty after.

"Would 1 p.m. be good for you?"

Can't argue that. I'm not doing anything important. Our rehearsal for the next show is only at.... SHIT, IT'S AT ONE! "Um... can we shoot for later?"

"But I normally go to a picnic with Angel Bunny at 6. And after that, I don't usually feel comfortable leaving the house."

Okay. That's bullshit. "Howcome?"

"Because I live just a walk away from the Everfree Forest. My cottage is about twenty-five hooves away from the treeline."

Okay, scratch that. That's a perfectly logical reason on why she doesn't leave her home at sundown aside from when she's coming from somewhere else. So, maybe it's best to schedule a day earlier. "How about Friday? I don't have my rehearsals on that day." I may have to ask for a day's leave though.

"I'm sorry. Friday is my time with the girls. I have breakfast with Applejack and the Cutie Mark Crusaders at 7 a.m., a spa appointment with Rarity at around 10 a.m., a fun session with Pinkie at about 1 p.m., 2 to 4 is where I'd normally help Dashie with the clouds, and if I get out at about 5, I usually help Spike around the library with Twilight."

A locked up schedule. Great. That leave me to ask a last minute leave for tomorrow. Why tomorrow? Because I refuse to stay here until Sunday, not to mention I have to patrol Cloudsdale that day. I mean Fluttershy is cute and all, but this town has been nothing but bad luck for me.

"Okay, then how about tomorrow?"

"Oh... um... I usually feed all the animals tomorrow. I don't know if I can."

Well this is a thing. I guess I have no other choice but to take a leave on Sunday, when I'm supposed to be on patrol. My weekend is going to suck now that I'm gonna have to tell Spits that I'm taking my Sunday off. I'm not gonna hear the end of it, am I?

"Sunday?" I squeaked out slowly.

"Well... I don't think I have anything planned for that day." The yellow mare pondered her schedule as she brought her hoof to her chin.

While she's doing that, I'm sitting her pondering if I should write in my request or tell Spits personally. On second thought, writing it in would be worse. I guess 'in person' would be better. "So... Same time?"

"Yes!" She answered quickly, almost scaring me on how quickly she jumped out of her wings. "So I will be waiting for you here at the town square at about 1 in the afternoon on Sunday."

"Yeah, Sunday." I'm dead when I get back to Canterlot.

"See you then."

"Okay."

As I watch Rainbow Dash and Fluttershy leave down the street, I could see the yellow pegasus take to the air, flying around like she was a young foal who just got through seeing one of our Wonderbolts shows. Oddly enough, it felt like that all over again. The only difference is that I kinda feel the same way she does. But of course, I kinda have to keep my cool, so long as I'm in a public view. But now that everything on this end is done, I can head back to Canterlot.

And this time, I won't be in the busted train cart.

Finally making it back to Canterlot, I managed to hit the office with a new story to tell. I was still lit with excitement from the fact that the mare I kinda crushed on asked me out on a date, so it seemed like very little could affect my mood.

"So I'm running for my life while these big ass brown bears are chasing me across town, literally running my ass up and down the streets screaming for help."

And then the smart-ass decides to ask a question. "So why didn't you fly-"

"INTERRUPT MY STORY AGAIN, CUMULUS! SEE WHAT HAPPENS!" In hindsight, he was more than right. I've shoud've taken to the air rather than run on the ground, but I sure as hell wasn't going to prove him right. Luckily, my immediate stupidity landed me a date. So in that loss was an even bigger win.

"So after I was cornered in a cave, a yellow pegasus mare with a pink mane and tail walked in and literally talked with the bears. After about a minute or two, they took their leave and I was left alone with this amazing mare who just so happened to be good with animals. After a long walk back to the center of the town, we hit it off until she finally told me that I was cute and that she wanted to go on a date with me."

"Aww, that's sweet! Soarin finally gets a date that isn't a crazy fan or a mare who's only interested for the money."

I could feel my entire being lock on to Cumulus. For each story I managed to tell, he had a comment that managed to irk me. If this keeps up, I may actually kill this guy. With a flip of my wing, I left only one feather extended to him as I looked away from him. Of course my response would cause him to get a laugh out of it.

This is what I put up with on a daily basis. But shit, I've got a date.

"So when were you planning to have this 'date'?"

And suddenly, I am reminded of why I dreaded coming here in the first place. Spitfire managed to come from the back room, walking into the conversation as if she had been in it the entire time. Just my luck.

"Commander... um..." I might as well get this over with. "Ahem! Permission to speak with you in private, ma'am."

Spitfire just looked at me with a quirked eyebrow, letting her eyes glide up and down as she walked towards her office. I only stood silent until she turned back around to speak to me. "Permission granted. Now get in here."

I couldn't believe my luck. I get a date with the mare I like and now I was going to have to face my boss on taking a leave on a day I have patrol. All of that cheerful energy have seemed to evaporated into thin air as Spitfire sat at her desk. Folding her hooves as she gave me a stern look, I could feel those eyes piercing into my body like sewing needles against my skin. I had forgotten how scary she can be in a serious situation.

"So... speak your mind, Lieutenant."

I swallowed the growing boulder in my throat as I tried to word my request as pleasantly as I could. "Commander, I am requesting a leave of absence this weekend."

"A leave... on what day?"

"Um... Sunday ma'am."

I could've sworn I saw an entire volcano erupt in front of me at the rate Spitfire busted into flames. "SUNDAY?!?"

Sheepishly, I nodded. "Yes. I am requesting a leave on that day.... ma'am."

"You have patrol in Cloudsdale that day, no way in hell you're taking a leave."

I had to go on that date. I'm sorry, but my duties can hold off on one day. I at least earned it. "Please Spits?"

"No."

Okay, I'm on my knees at this point, praying to her as if she was some sort of deity. "I will do anything for a leave."

"Request for leave has been denied." And she shoots down my prayer like a sniper shooting at a can from point-blank range.

"Why?"

"Because a date is not an emergency."

She starts to make her way to the door, but in a last-ditch effort, I throw myself in front of the door, barricading myself against the wood. "But we've already scheduled!"

She tries to navigate her way around me, but with the added obstruction of my wings, she goes nowhere. "Furthermore, I don't think that a date is in your best interests right now. You don't need to go on a date."

Suddenly, it dawned on me what was really going on. The way she exploded at my request, the way she entered the room as soon as I mentioned that I was going on a date. The shoes were definitely fitting. "Oh, now I get it. You're jealous!"

I could see her jealousy creeping out of her eyes as she blinked, baffled that I'd call her out on what was really going on. "Excuse me?"

And now that I've had the high ground in this argument, it was time that I took advantage of it. "You're just jealous that I'm going on a date this weekend and you won't have one. So is that it?"

Flustered and pink on the cheeks, Spitfire bolted directly in front of me, merely inches away from my face. "How dare you! Making those kinds of excuses are out of order!"

"Yeah, but so is not letting me leave when I have at least fifteen days of leave left."

Spitfire stormed back to her desk as she pulled open a drawer. As she reached in, she pulled out a stress ball and started compressing it between her hooves as stared at me menacingly. "You're not leaving, and that is final."

"Argh! Why not, Spits?"

"Because I ordered it."

That's a stupid reason. That's like when my mom says I can't play with my toys because 'she says so'. I'm going to need a better argument than that. "What's the real reason?"

"I don't need to speak with you anymore Lieutenant. Now stop wasting my time and get back to your station."

As the ball compresses in Spitfire's grasp and returns to it's spherical shape, I feel my brain being treated the same way. My patience is being toyed with, and I was not going to leave this office until I got a legitimate reason on why I couldn't use one of my days of leave. Better yet, I want the real reason I can't go on my date. "I'm not leaving until you tell me why I can't leave. And I don't want to hear a damn thing about protocols."

Spitfire continues to squish the blue ball, now increasing her pace. "I just don't think it's a good idea for you to leave on your patrol day. What if Cloudsdale gets attacked?"

"The war is on the far outer reaches of the Equestrian border, way out of Cloudsdale's migratory patterns. I think that it would be fair if I can get a day off since I've earned it."

And then, the truth finally came out in the form of an implied statement. "So you'll take a day off for her? She must be some mare."

I won the argument. Everypony stop the presses. I won an argument with a mare. "See? You are jealous."

At this point, I feel so sorry for that tiny ball in her possession. Any more of this abuse and that thing would bust from the pressure of her hooves alone. Poor little fella. "Maybe I am. But that isn't weighing into my decision. Otherwise, my answer would still be no."

I try to argue with her for my leave now. At least I managed to make her admit to her being jealous. Sort of. "Please be reasonable."

"I am being reasonable. You come to me last minute, you request a leave on a day when you know you have a duty to perform, and you're doing it for something as mundane as a date. Not even a legitimate emergency."

Okay, those are some valid reasons. But I still earned my fifteen days of leave. There's only one way I can negotiate with her in this matter. "I'll make it up in rehearsal on Saturday."

Wonderbolt rehearsals. The one day where she really feels like a free spirit. I can't believe how amazing she is when she just lets everything that weighs her down drop to the dirt as she takes to the sky. She loved that part of the job, and she loved being able to tell me what to do even more. Aside from that, I think that I'm going to enjoy this. "...You'll be running double drills."

Or not. WHAT THE FUCK! "Double drill's? That shit's insane! I'll be up all night doing tha-" I'm met with a very dark stare, one that screams 'shut the hell up and take the offer or else'. She wins that one. "Okay. Double drills."

A smirk shows up on her face as she finally spared the stress ball of an untimely fate, dumping the poor little guy into her drawer. "Triple, I changed my mind."

I felt my jaw hit the ground, jump into a wormhole and out of a portal on top of my head. My jaw just breached the laws of physics. That's how far it fell. "That isn't fair, Spits."

"I've altered the deal, pray I don't alter it any further."

I can't believe that this is what my date has come down to. One single day for myself and I only have to go back into 'hell-day' mode when I was in basic training the day before. I know that she's my superior, but still... "Okay... triple." What a bitch.

"Request for leave, accepted."

I moaned in agony as I realized what I had managed to agree to. One drill was already tiresome on it's own. But to do three? That's damn near suicide. Well, you keep what you kill. "What is triple drills going to do to me anyways aside from wear me into paste?"

"That's pretty much it."

Her sarcasm knows no bounds. "Ha ha. Very funny."

"So, who's this mare you're going with?"

"She lives in Ponyville."

Reflexively, Spitfire just laughed at my answer. "A ground flier? And here I thought you had standards."

"She's good with animals and she managed to save my hide from a pack of hungry bears." I said, trying to defend her.

"So, it's a life debt?"

Yeah, let's go with that. "Yup! Caught me red-hoofed." I lied.

The yellow mare just rolled her eyes as she shook her head as she got back to her paperwork. "Okay Soarin."

"What's that all about?" I asked, wanting to understand why she seemed to be so condescending about my date.

"I'm just saying you could do better."

Bitter as all hell. "What's wrong with what I've got now?"

"Well for starters, you don't know what she's like."

Spiteful as fuck. "I could say the same thing to you."

"Okay, Soarin! Get out of my face!"

Green with envy. Strike three. I'm out of here. "Great. I guess I'll go on ahead and get back to my station."

"You do that."

I turn around to take my leave out of the door. As soon as my hoof reached the handle, I could hear Spitfire speak to me. "Oh... one more thing."

"What's up, Spits?"

"Quadruple. Drills."

Those words seemed to hit me like a ton of bricks. I didn't even know that quadruple drill even existed. But once more, Spitfire always finds a way to bend me over and take me for a ride. "Fuck me."

She playfully snaps back. "I offered that a long time ago. Your loss."

Sometimes, I hate my job.

Author's Note

Wow, an update? I guess it's about that time to put on the tinfoil hat. Sorry if this chapter seems a bit off. I had to get myself back into writing this one. But in all, I guess I have some work to do in order to get this ball rolling again. Just kinda keep your eyes peeled for any updates, I have a myriad of other stories I'm writing and I don't know if I can catch up with them all.