Try as I May. Try as I might.

by PredictableOffender

Date Night

You are in the local food market, ever since you started spending your days with Twilight you had acquired a taste for finer foods, even if Twilight eats like a spoiled 12 year old. You have never seen her eat healthy and she is an extremely picky eater, kind of like your 12 year old self. While you are thinking about Twilight you feel Harvey jerk on his leash, you turn to see what has him so excited.

“Hi Winter.” You turn round to see Twilight in a tight-fitting vest and blouse and an unusually short skirt.

“Oh, hey Twilight.”

“I was looking for you, I wanted to surprise by uhhhh.... ” Twilight stammers then mutters something to herself.

“She said she should have done this a long time ago.” You hear the Hooded Child's voice behind you.

“We should go on a date today...” You take a moment to register what she said.

“Alright, I just gotta make myself more presentable.” Twilight is shocked at your words, she pauses for a while.

“Can I come with you? I want to see what your apartment looks like.” As unprepared as you are you cannot say no.

You finish your shopping with Twilight and begin to walk home when she stops you. She offers to drive both of you back to your place, you gladly accept so she leads you to her dark purple Pyromancer hatchback. You put Harvey in the back seat, then get into the passenger seat next to Twilight.

Twilight rolls down the back window for Harvey and you are both soon on the road, Twilight drops Harvey off with Spike at her place. You give her directions to your place, it doesn’t take long before she pulls into the parking lot and the both of you disembark the car. When you get out of the car you can see Twilight staring at you expectantly.

“Do you like the outfit. You seem like the scholarly type so I thought you would like the School-girlish outfit I picked.” As if to exaggerate her plight she blushes and shrinks away from you as she says that.

“I think you look great.” She perks up when you say that. “I have to get myself to halfway passable.” Twilight giggles.

Twilight follows you as you pass through the lobby and the stairs to your apartment, you arrive at the door and unlock it. You open the door and let Twilight go in first, there is no point in hiding anything from her.

“Wait here Twilight. ” You turn and walk into your bedroom. When you enter the bedroom you are struck with the question of what to wear, you have plenty of proper clothing from before but you need something more country. You pass your 3 piece suit and immediately dismiss it, however you can pillage the vest from it. That gives you an idea, you grab a white undershirt and you short sleeved dress shirt. You know sweet fuck all about what color goes with your blue undershirt and black vest so you grab a pair of black dress pants. You grab black socks and a pair of your good shoes and get yourself dressed, you look at yourself in the mirror and notice something is missing. You rush into the bathroom and for a shave and to fix your hair. You wonder if you even got your hair cut once since Canterlot.

You step back to admire yourself in the mirror, you did a good job at cleaning yourself up. You flex your exposed arms, all the work you really does pay off in more than one way.

You walk into the living room to find Twilight looking through your personal book collection. She grabs an old textbook from Canterlot and begins looking through it, you can tell she is feeling nostalgic about it. Wait, you never told her about Canterlot.

Shit!

You might have some explaining to do.

She closes the book and holds it to her chest and says something to herself. You take this opportunity to walk into the room and present yourself, Twilight nearly screams at your sudden arrival. Her face has turned almost completely red, she tries to hide the book behind her back. You notice her cast a teleport spell behind her, the book is still there afterwards though.

“Hahaha... oh... Hi... Winter... ohhh You look amazing.” Twilight stumbles a bit before placing the book on the counter. “I, uh, can we get going? I have a friend working at Sugarcube Corner.” She is shaking, why would she be nervous about that book? Does she remember? Wouldn't she say something about it? You decided to dismiss the thought and be a gentlemen so you lead the blushing and shaking girl back to her car. You pass the Hooded Child on your way to the car.

“I have to talk to him at some point.” You think to yourself.

“You don’t have to. I am all in your head.” He responds, but you ignore him. “I mean what kind of psycho are you?” You ignore him.

You offer to drive and Twilight accepts, she is still really flustered. You start the car and you are soon driving your way to Sugarcube Corner, you stayed silent because the Hooded Child had unnerved you a little. You reach the parking garage nearest to Sugarcube Corner, the way Ponyville downtown works is stupid.

The mood instantly lightens when you arrive at Sugarcube Corner, the giant cupcake shaped building can cheer anyone up. The two of you walk in and sit down in the cafe section, Twilight flashes you a smile.

“Sorry if I’m so nervous I’ve never been on a date before.” Twilight says.

“What.” You mentally slap yourself for saying that out loud. “It's just amazing a girl like you has never been on a date.”

“Well, I was always a bit of a shut in. Even after I started bearing the elements guys just never approached me.” That's right, she is the Princess of Friendship, you were still thinking of her as an underclassmen. You suddenly feel a lot luckier.

“It's alright this is my first date too.”

“Oh... Thank you Winter.” When Twilight says your name, your heart skips a beat.

“Anyway, I kind of want to go target practicing again.” You wave your hand to dismiss the topic.

“I’d rather you not.”

“Come on Twi.” Your own words surprise you and Twilight.

“Not many people call me Twi...”

“Oh.”

“Nononono It’s alright. But anyway the last time you were target practicing you injured yourself.”

“Bring a first aid kit.”

“That's the thing. Your symptoms were similar to mild to severe blood loss, It's like you ripped the oxygen out of your blood.”

“That’s weird....”

“Awww! You two are so cute together!” You hear Pinkie Pie swoon behind you.

“Hello Pinkie.” Twilight says, completely unfazed by the sudden intrusion.

“I know we normally don’t take orders here, but I get your favorite drink for Twily and something for her boy toy! ”

“Wait. What?” Pinkie pokes your arms and somehow gets you started flexing.

“Come on don't sell yourself short hotstuff!” Pinkie tackles you from behind and starts hugging you. “I’m jealous of you Twilight. I’m not jealous of Rarity though, her boyfriend is scary.” Pinkie disappears, you try to look for her, but find nothing.

“I forgot about her.” You turn to see Twilight was laughing at you the whole time.

“It's alright, you'll get used to her. Although she got me thinking, you don't have any friends here do you?”

“Not really.” You say, you can maybe count your boss.

“I can introduce to my friend Caramel, he is running the mud race in a few days. Rarity’s boyfriend Silves is are gonna compete too, along with my friend Applejack’s brother Big Macintosh.”

“Sounds like fun watch.”

“We should go together, they set up a carnival around race!” Twilight embarrasses herself with her outburst. “It'll be so much fun.”

“Coffee’s ready!”

Pinkie had taken you the same sickeningly sweet drink that Twilight always orders, you try to hide your displeasure but Twilight caught on quickly. The two of you have a lively conversation and wind up spending hours at the small bakery in the town square.

Since you have all day to spend with Twilight you decide to go back to the library with her, once you are done drinking you decide to pay.