Date 1: Venice

Jack arrived at the Nightmare King's lair in the early evening. It wasn't dark out yet, but it was about thirty minutes until sunset. The young teen felt like butterflies were battling in his belly as he stood outside of the lair a good five minutes. Leaping into the darkness that lead to Pitch he landed lightly on the cool stone ground inside the main cavern by the desolate globe, and straightened out his clothes as he scanned the room for Pitch.

"Good evening Jack." Pitch purred ascending from the shadows of the globe.

Jack had already suspected the Nightmare King would try to sneak up on him, so he just turned and smiled at the older spirit.

"Hello." Jack threw his hand up in a short wave of greeting.

The young guardian hardly had experience socializing and dating, so he felt awkward. It was common knowledge to the both of them that the attraction was mutual to some level and the young guardian didn't know how to act. A blush graced Jack's cheeks thinking about it and he looked to the side. Pitch caught the blush and chuckled to himself.

'Frost can be so adorable.' "You are early." The Boogeyman purred approvingly.

It's amazing how the teen could have total lack of responsibility but actually able to demonstrated it when needed. Jack's face only blushed more at the approving tone in the Nightmare King's voice. Wanting to shake off his awkwardness Jack decided to contribute to conversation.

"So.. What are we doing tonight?" He couldn't hold back his curiousness no matter how out of sorts he felt.

"I thought that we could go out for a relaxing evening. Not something full of activity, but maybe where we could hold pleasant conversation and eat." Pitch's voice was calm and smooth.

'How is it his voice can be so relaxing and alluring?' Jack thought to himself.

Upon receiving no response Pitch furrowed his brows thinking maybe the winter sprite wanted to choose the activities for the first date.

"Unless you would like to choose what and where we go tonight." He stood up tall and put his hands behind his back with a look of concern.

"Oh no! I was just thinking to myself. What you have planned is fine." Jack answered trying to make it clear that there was no negativity in his thoughts.

Pitch smiled and sighed looking relieved. "Good, because I already have everything set up for our outing. Shall we then?" Pitch smiled and put his elbow out for Jack to loop his own arm in.

The young teen surprised by the simple gesture took the older spirit's offer with his mouth slightly parted. Who knew the Nightmare King could be charming and debonair? They walked into the shadows together where they disappeared from the lair. Jack's stomach flip flopped as they traveled through the shadows, and he held his breath as the crushing pressure pressed against his body. Within moments the pressure released his body and he felt a cool breeze caress his skin as if the wind was checking on him. The white haired teen opened his eyes and his mouth dropped.

"Woah…" Jack looked around amazed at the sight before him.

The roof before him held a candle light dinner for two. A black iron table held a bucket with a chilled bottle of wine and two wine glasses sat before it. Silver cloches sat on either side of the table, along with silverware and thick black cloth napkins. The black iron chairs that sat at the table ends had black velvet plush cushions. A single candle and a vase of white and red roses sat in the center of the table. The stars shone brightly in the night sky, and the view of the city was incredible. In the background you could hear the opera beginning giving the perfect effect on the setting. Jack stood there mouth open for a few moments.

Pitch chuckled at the teen's reaction. He was sure that this would be a surprise for the teen, but the reaction of total shock was priceless. Jack looked to him smiling glassy eyed in a daze.

"You brought me to Venice for our first date?" The young guardian asked with a smile of nervous excitement.

"Well, this is the first date. I wanted it to be something special." The Boogeyman answered honestly. "Shall we sit? I hope you are hungry. I prepared Veal Saltimbocca alla Romana. It's a Roman dish." Pitch remarked making a slight bow to Jack with his hand gestured to the table.

The winter teen swallowed noticeably walking toward the table feeling nervous. Pitch had gone through all this effort just for him? When he reached his chair the older spirit pulled his chair out for him gently, a sincere smile pulling the sides of his lips up. Once Jack was seated Pitch sat and turned to the side. Beside the table there was a serving cart that held another cloche and extra napkins. Pitch took the lid off revealing bruschetta. He then uncovered his and Jack's plates causing the magnificent aroma of food to fill the air. Once the lids were tucked away onto the serving cart Pitch popped the cork to the wine.

"Would you like some red wine? It's Italian; Brunello di Montalcino and especially good with this type of dish." Pitch offered politely still smiling.

"Um.. Yes. Yes, thank you." Jack responded shyly looking innocent.

Pitch poured him a glass trying to make sure he didn't pour too much. The Nightmare King wasn't sure if the teen had much experience drinking alcoholic beverages, and he didn't want Jack getting too tipsy. He then filled his own and placed his napkin in his lap. Jack followed Pitch's example placing his napkin on his lap.

The winter sprite didn't have much experience in fine dining. Alright, to be completely honest he had no experience in it. His way of eating for the past centuries had been stealing food and stuffing it into his mouth without bothering with things such as silverware or napkins. Before that he was just a mere peasant in his town and he lacked table manners even then. He observed how Pitch used the utensils and copied his actions, right down to the portion of meat cut off to eat. Jack's eyes opened at the delicious taste, and barely swallowed before speaking.

"This is amazing! You really cooked this?"

Pitch smiled pleased and amused. He knew already that the young guardian lacked table manners, but he was pleased that the teen made an effort to be polite.

"Yes. I enjoy cooking and good food." Pitch answered truthfully.

Jack nodded feeling nostalgic. He often ate certain foods or candies because of the memories associated with them.

"Is this your favorite kind of food?" The teen asked not wanting the moment to get awkward.

"It is one of my favorites."

The rest of the dinner contained light conversation between bites of food and sips of wine. The topic ranged from the places all over the world to different cultures and how it effects society.

"So, it's like no matter where you are some things are always the same." Jack concluded finishing on what he believed of the humans.

"Indeed." Pitch agreed.

Now that they finished their food and conversation came to a close, the Nightmare King placed his napkin onto his plate and stood. Jack watched and did the same.

"Thank you for the dinner." Jack said shyly blushing. He wasn't sure if this was the end of the date.

"You are very welcomed. I had something else planned for tonight, if you're not in a hurry to end the night." Pitch said looking hopeful causing Jack to smile.

"I don't have any where I have to be." Jack answered trying to make himself sound indifferent, but the excitement leaked through.

"Then we shall continue." Pitch said with a smile much too wide for his character.

Pitch formed a cloud of nightmare sand beneath them and lowered them to the canal. The nightmare sand formed into a gondola upon touching the water, and a human-like figure formed with a pole in hand. The Nightmare King sat down and gestured to the vacant spot beside him.

"Please do sit." The Boogeyman practically purred to the teen.

Jack's cheeks flushed bright red as he sat beside him. He felt like the little white lamb being lured in by the big bad wolf. The Nightmare King laughed at the face he was making.

"Don't worry, I shall not do anything. It is the first date after all." Pitch remarked causing the winter teen's cheeks to turn an even brighter red.

Jack crossed his arms over his chest and looked away feeling embarrassed.

"I wasn't worried." He remarked defiantly puffing his cheeks out.

It made the teen look all the more innocent and Pitch chuckled deep in his throat.

"Of course you weren't." Pitch commented as he caused another figure to appear from his sand.

This one was a smaller human like figure and held an instrument from nightmare sand. The figure put the instrument to his chin and started to play. Classic violin music began to play. Jack watched the figure in awe. He didn't know Pitch could do that. The nightmare sand violin sounded the exact same as a real one!

"Would you like some gelato for dessert? It's chocolate mousse." Pitch held a glass cup towards the white haired teen.

Jack blinked a few times at the dessert. Where the hell did Pitch get gelato from?

"It's really cute when you're confused." The Nightmare King chuckled to himself.

The frosted teen pursed his lips narrowing his eyes, but took the chocolate treat none the less. Don't judge. Priorities here…. Chocolaty goodness is important. Jack pouted his lips a little.

"I wasn't confused. I was just surprised.. that's all." He took a bite of the chocolate dessert and his eyes lit up. "Pitch! This is amazing!" He said excitedly causing Pitch to smile.

"Good. It is one of my favorites." Pitch said before taking a bite of his own.

"I didn't know you had a sweet tooth."

"There's a lot of things you don't know about me yet."

"I guess so."

The next hour passed with them talking learning dislikes and likes about food and music. They were amazed with how their tastes for certain things mirrored each other. Jack had admitted he liked some classical, but the Nightmare King definitely had a mild obsession with it. Pitch detested country music all together, and Jack teased him by singing part of Achy Breaky Heart.

The gondola came to a stop and Pitch stood. Stepping out of the gondola he helped Jack step out of it even though he didn't really need to. Pitch really did have a debonair side to him. It was actually quite charming to the winter teen.

The nightmare sand dispersed and the two stood quiet for a while. It was getting to that point of 'How do we say goodnight now?'

"Would you like me to take you back to my lair?" Pitch asked quietly.

Jack looked at him with surprised expression. Was he trying to pull something? The Nightmare King lifted his hands up in a placating gesture.

"I mean we left from my lair. I didn't know if you wanted to part ways here or not." Pitch quickly said to dismiss any other intentions the teen could have been thinking.

"Oh.." Jack looked down and ran a hand through his snow white hair. "Um, no. It's alright." He looked up and gazed into the Nightmare King's mesmerizing golden silver eyes. "Thanks. I mean, thank you for the date. It was nice." The teen said nervously.

"It was my pleasure young Jack." His voice silky and smooth. "Thank you for joining me." Pitch took one of the winter teen's hands and kissed the back of it.

Too shocked to do anything Jack just stared with his lips partially parted.

"Good night Jack." Pitch said backing into the shadows. "See you tomorrow." He disappeared into the darkness.

Jack stood still for a few moments. Stunned he put his other hand over the place Pitch had kissed blushing like a crazed teenager. The Boogeyman's lips had felt hot and it was like electricity. The teen's insides felt giddy. He felt happy. It felt like he was dreaming.

With a sudden burst of energy Jack bolted into the sky laughing happily. Pitch watched the teen from the shadows of the roof amused. He couldn't stop the hope and happiness swelling into his black heart.

"All this over one little winter sprite." The Nightmare King sighed.