"Sombra?"

The umbrum looked up from his large, black leather bound book and peered curiously at Twilight, picking up on the hesitation in her voice. He put the book aside and held her closer on the library sofa they'd been lounging on. He asked, "What's wrong, Twi?"

Maybe she's finally going to say that she's gotten tired of you.

Instead, Twilight replied nervously, "If you're not doing anything later, I was wondering if...maybe you'd like to go out?"

Sombra blinked. "Are you...asking me out on a date?"

"Yes. It's just that, since we're dating, I thought it'd be time that we went on an actual date."

"True, it's just that this is a little...unorthodox. I mean, a mare asking a stallion out? It's a tad bizarre."

Twilight poked him in the chest. "Hey, nowadays it's not a big deal. A mare can ask a stallion out if she wants to."

"Really? Huh. Times truly have changed since my time. Very well then, I accept."

Sombra noticed Twilight's retreat into herself and frowned. "Are you alright? I said, 'I accept.' You're acting as though you've never done this before."

"Well...that's because I haven't."

His jaw hung open. How a mare as stunning and bright as Twilight never been asked out on a date, or asked somepony to go on a date, was beyond him. "Well, in all honesty, I thought you did pretty well."

"Thanks," Twilight blushed as Sombra pulled her towards his bare chest. She'd asked him to keep his armor off whenever they had down time and he was all to happy to oblige. Who knew that the King of Shadows loved cuddling? "So...what would you like to do?"

Take you to the tallest tower and push you off of it.

Oh, if only you had a throat so that I may strangle you!

It took a moment for Sombra to decide as he didn't want to screw up his first real date in over a thousand years. An epiphany hit him like a brick and a sly grin formed on his face at the idea. "Why don't we go out for our first date?"

"You mean outside the castle?"

Sombra leaned in closely as is revealing a huge secret. "No, I mean outside the barrier. We can try out this place I read about known as 'Manehattan.' See if it's as great as advertised."

Twilight jumped a little and Sombra couldn't help but chuckle at this. "Whoa, whoa, whoa! You want to go to Manehattan? What if you're caught being outside the Crystal Empire? The princesses will be furious to find out that you've-..."

"Hey, what's the point of living if there's no risk involved? Trust me, it's a risk I'm willing to take." Sombra placed his hoof underneath Twilight's chin and tilted her face up to lightly kiss her, relishing the taste of apricot on her lips. "For you, I'd defy a million princesses." He ran a hoof through her mane and gazed into her eyes, losing himself in those oceans of violet as he felt her hitched breath on his neck. No, I'd do more than that. He realized with startling clarity. I'd die for her.

"O-okay. But how are we getting there? I think ponies are going to notice a giant flying shadow."

Sombra smirked, "Let me worry about that. Just wear something nice."

Okay, relax, breath. Twilight looked right and left, hoping to catch glimpse of Sombra soon, half-hoping that he'd abandon the whole idea and they could a quiet evening in the castle. Lilac Luster had dressed her in a red, off-the-shoulder evening dress with a pearl necklace and white gloves. Her mane, which had grown considerably longer in the past few months, had been styled into a Prench twist with some bangs hanging over her right eye. Both Lilac and Amber assured Twilight that she looked beautiful and for once, she felt it and was confident that Sombra would think it regardless.

"Waiting for somepony?"

Twilight turned and found a light gray unicorn stallion leaning up against the main foyer wall, dressed in a sharp black pinstripe jacket and tie as his light green eyes danced playfully. He had his feathery black and cobalt-streaked mane slicked back and this time, his cutie mark was a glass retort filled with a bubbling blue liquid. As strange as it sounded, Sombra's fake forms were somewhat distractingly unnerving to Twilight. True, both of them were physically appealing but they were also off-putting to her. She found the real Sombra so much more handsome and was much more comfortable with him as he was rather than whatever form he had to take.

"Yes, my coltfriend."

Sombra pushed himself off the wall and casually strode over to Twilight. "Oh yeah? Good looking guy?"

Twilight smirked, "Oh yes, very handsome. Dark and intense but roguishly handsome."

"Well, whoever he is, he's a lucky stallion. You are absolutely stunning." He took her gloved hoof and tenderly caressed it. "Are you ready to go?"

"Yes but how are we getting there?"

Sombra pulled a gold bracelet inscribed with ancient symbols from out of his coat and placed it on his right wrist. "I found this teleportation ring in the Hidden Gallery. It'll be able to take us wherever we want to go." He held out his left foreleg and beckoned her towards him. "Will you please kindly?"

Twilight slipped her foreleg into his own and watched as he twisted the ring three times to the left. The ring glowed with a dim gold light that then engulfed the two in its glow. Everything whooshed past them, giving Twilight the sensation of being a rubber band being stretched to its limits. There was a bright flash followed by a loud pop before she found herself standing at the foot of the Emsire State Building as throngs of Manehattan ponies bustled by, too busy to notice the new arrivals.

"Wow, that's one way to travel!" Twilight marveled as she glanced around. "So, where are going?"

Sombra pulled her close and grinned, "You'll see. Come, the night is young and so are we. Well, you are."

They caught a cab and were taken to a real fancy restaurant called Horsia, a large rectangular, three-story building with a glass dome and a large sign displaying the restaurant's name in blue cursive. They passed through the steel double-doors and a line of disgruntled ponies to meet with the rail-thin teal-green maître d'.

"Welcome to Horsia, sir and miss! I hope you have a reservation, hmm?"

Pulling Twilight close to him, Sombra leaned forward and flashed the maître d' a large, nonthreatening grin. "Of course. It's under the name, 'Mercury Sun Gold.'"

"Ah, here you are! Table for two, hmm? Enjoy."

A crimson stallion bowed and began to led the couple to their table, allowing them to inspect the restaurant's art deco design, which featured rectangular columns, white-and-black checkered floors and metal geometric wall decorations. They climbed the stairs to the second floor, passing a group of well-dressed stallions showing off their business cards to one another. All of the stallions seemed to look exactly the same, though this could've just been Twilight's imagination. When they arrived at their table, they found that is was situated behind a room divider with zigzagging patterns on the frosted glass and beneath a pillbox-shaped ceiling chandelier. Upon being seated, the waiter handed them oversized menus and inquired about their choice of beverage.

"Oh, I'll have cranberry juice with extra ice," Twilight smiled and brushed a lock of hair out of her eyes.

Sombra shook his head. "Come on, Twi, we're here to celebrate! Bring us a bottle of your finest champagne!"

The waiter jotted down their order and bowed before taking off at a brisk pace. Twilight looked around at the restaurant, hardly believing that she was there. Her hoof slid across the table to grip Sombra's. "So Sombra, how're you enjoying the modern age?"

"I'll admit that it takes...some getting used to. For example, this restaurant setting. How do they light this place without candles or lanterns? Are they using...-" He peered at the chandelier above them. "...-Magic enclosed in crystalline ampoules?"

Twilight snickered and shook her head. "No, they're lightbulbs. Basically, it's a glass or ceramic bulb with a wire filament charged by an electrical current, creating a source of light."

"Electricity in a little glass bulb? Science surely has advanced since my day!"

They talked about literature and philosophy, comparing and contrasting the similarities and differences of the topics based on both Sombra's time and that of modern Equestria. Once their drinks and food arrived, they really began to enjoy the opulence of their surroundings, sipping champagne as a stringed instrument band played some Neighthoven. Twilight's panzanella salad was simply divine while Sombra equally enjoyed his pasta primavera. Something tapped Twilight's left hindleg and it took a minute for her realize that she and Sombra had been playing hoovsies, an activity she once thought stupid and juvenile that had taken on a whole new meaning for her. The waiter cleared away their plates as the band began playing something slightly more energetic, creating a smirk on Sombra's face.

"Why don't we join everypony else on the dance floor?"

Twilight followed his gaze to the ponies below them and shook her head. "No, sorry, can't do that."

"Why not?"

Twilight nervously clicked her hooves together. "I...don't know how."

Sombra stood up and extended his hoof. "It's okay, Twilight. It's just a slow dance. Surely you've done that."

When she failed to respond, Sombra knelt down and whispered, "You'll be alright, I promise. Just one dance." He then rose to his full height and again held out his hoof expectantly.

Sighing in defeat, Twilight slipped her hoof into Sombra's larger one and they soon found themselves on the sparse dancefloor, surrounded by couples of varying ages and shapes. "Here, I'll show you." Sombra placed Twilight's forelegs around his neck and then followed this by placing his hooves on her waist, creating a light blush on her cheeks. "And now...we...just sway. Just like this." Twilight had to smile at this. Once she took away the stigma of the newness of this particular social activity, it really was quite easy. She sighed and placed her head on her partner's chest, listening to the steady beat of his heart, lulling her into a state of pure calm.

"Twilight?"

"Hmm?"

"I..."

She felt his chest heave slightly, his heartbeat increasing. "I'm just happy to be here...with you."

A sweet smile crossed Twilight's lips and she exhaled happily. "Me too. Nowhere else I'd rather be."

Author's Notes:

Sombra's wish to strangle the Darkness is a paraphrase of a quote by serial killer Carl Panzram (1892-1930): "...I wish you all had one neck and that I had my hands on it." Yeah, I know it's pretty dark but I think we already passed that point awhile back.

I based Twilight's look in this chapter after Julia Roberts in Pretty Woman

I refer to the bracelet as a "ring" because it's a circular, hoop-shaped object.

Emsire State Building=Empire State Building

Neighthoven=Beethoven

"Horsia" is a play on the name Dorsia, the fictional restaurant from American Psycho