====== Chapter II ======

Jackk was pacing back and forth in his living room as he was kind of scared of such a simple thing, however he was one to overthink way too much for his own good

‘Why did i accept this..” he muttered anxiously to himself, brushing his charcoal grey mane back as he sighed “Fuckfuckfuckfuckfuck..” He added, stomping his hoof lightly as he soon heard his stopwatch chime

Ring ring ring!!

That meant it was time to head over to Winter’s place for what would be a very embarrassing night.

Heading out his front door, Jack hid his embarrassment and shyness through a content smile as he began trotting forward, it was even quieter than on his way home, most ponies were home now, either making dinner or spending time with others, any tourists were in their hotel rooms relaxing, and any ponies out were admiring the well lit streets coated in crystals

Jackk had often walked through these streets at the evening/might and so did many, it was calming to see the illuminated city and hear the calm current of the river nearby in the distance, it was also a nice place to meditate and just get away from all the hectic ponies and businesses around

“I’m so nervous..” The stallion had whispered to himself in a pitiful manner, he knew he’d probably be proven wrong eventually, but his heart was beating out his chest and he couldn’t help it

After walking through the city’s square he was almost at his destination, and he got more hesitant as he got closer, nevertheless he managed to toughen up and reach his home

Knock knock knock !

Winter jolted up from his seat as he heard the hoof knock on the door “Eep!” he squealed lightly as well

As Winter got up from his seat he brushed himself off and spritzed on some cologne, he headed to the front door and happily greeted the stallion

“Hey Boss!” he said with a warm smile and enthusiastic tone

Jackk blushed quite a bit from the term as he smiled weakly back at him “H-hey.. Uh- Winter” he soon replied with a giddish grin as he kept a bit of distance from the door

“Are you ready for dinner?” Winter soon added as he stared at him with a small blush, keeping a playful grin in his direction

“Reaaady as I’ll ever be” he replied with a awkward smile as he rubbed his other hoof with his own

Winter grabbed a light blue silk scarf and soon headed out the door, closing it behind him as he looked back at Jackk with a warmer smile and nodded his head in the direction they were headed so Jackk could lead the way

“After you!” Winter said enthusiastically, and shortly after the grey stallion had done so, trotting forward and onto his way to a more lowkey middle class restaurant for them to eat at. He wasn’t much of a fan of fancier things anyway

“So uh.. Why did ya decide to work at the library?” Jackk said as the stallion averted eye contact towards the other, not even caring if he looked shy

“Oh well, i needed something to do while doing all my school work for college!” Winter replied, staring up at the larger stallion with his dorky grin

“Oh? What are you studying for hmm?” Jack asked in return as he tried starting up a conversation, after all, no guarantees he’d talk much in public.

“Well i really like cooking so i decided to do some studies on it” Winter gestured “I started cooking when i was a filly!” He soon added

“Really? That’s nice, i’d love to try some of your food sometime” Jack replied with a cheeky grin as they walked down the empty streets of Canterlot

“What about you? What do you wanna do in life?” Winter said.

“I like magic.. And the science behind it, and spells are cool too” Jackk said while scratching the back of his head

“That’s really cool!” Winter replied loudly

That caused Jackk to blush quite a bit from the compliment as he smiled dorkishly as well now, his hoofsteps were also starting to pick up which he did when he got nervous

“Thanks” he replied after a few minutes of awkward silence

“No problem bud!” Winter said with a happy glee as he nodded his head

After awhile of walking and chit chatting the couple had made their way towards the restaurant and went inside, the place was well lit with candles and a few strands of small lantern bulbs, Jackk had made his way up to the reservation desk and cleared his throat as he was about to die from embarrassment by saying

“Reservation for two, sir” Even though the two weren’t actually a couple he still felt awkward in applying that

“You got it!” the waiter said with a small grin as he winked at the two, which of course made the grey stallion’s heart drop to his stomach

“Th-Thank you, sir” Jackk soon said to him as he trotted along, grabbing a menu as well

“Thanks!” Winter also said as he soon followed behind the other

The restaurant had more of a diner feel rather than a elegant restaurant that the inner city had, Of course the gentlecolt Jackk was, he pulled out a chair for Winter to place his flank on as he soon seated himself across from him, such a gesture made Winter blush a light tint of pink

“Thanks for agreeing to come J, after all you didn’t have to” WInter said as he looked around the eating establishment

“It’s no big deal.. I don’t go out often anyway” The unicorn said in a soft chuckle as he looked around as well, trying to ignore the fellow ponies in the restaurant as he didn’t wanna get too nervous

“Still, i appreciate it Boss!” Winter chirped out as he smiled warmly at the grey pony who was being shy and sorta closed off from the other

Jackk picked up the menu that was on the table, eyeing through it to see if anything peaked his attention, and a few entrees did as well a desert displayed on the menu

“Lemme know when you’re ready to order” Jackk said to Winter as he kept his muzzle engulfed in the menu to avoid noticing the other ponies

“I think I already am” Winter quickly replied back as he set his menu down “Are you?” he added

“Uhh yeah, i think so,” Jackk set the menu down and took a sip of water before shouting… somewhat “Waiter!” His voice was still calm and didn’t have a lot of umpf to it, though he waved his hoof and a waiter did soon trot over

The small male Pegasus with a silky green coat and a soft charcoal grey mane had flipped his note pad and gotten his pen before asking “What can i get for you two tonight?”

Jackk looked at Winter before nudging his head in the direction of the waiter, implying him to order first

“Oh- I’ll have the carrot salad and hayburger!” Winter said, and as the waiter looked at Jackk the grey stallion cleared his throat

“I’ll have what he’s having” He soon said, it was actually a coincidence as he did want both those items, The waiter wrote down their orders and soon trotted off to the kitchen

“Was that actually what ya wanted?” The white pony asked

“Indeed, actually it was” Jackk agreed with as he nodded, crossing his hind legs as he stared out the window

“So uh- Tell me about yourself” Winter said as he leaned onto the table a bit, taking interest into the other stallion

Jackk bit his lower lip as he pondered his thoughts, he didn’t have a very happy life and he didn’t wanna make this dinner sad especially

“I- uh- I didn’t have a good life so far” he simply said, looking away even further from the other

The reply made winter frown immensely so, he didn’t like hearing such things mainly cause he had a tender heart, and cared about many

“Well, I’m here to listen, if you wanna share of course.. No pressure” the small fluff ball replied with, he had a bright smile on his face in hopes that the other would feel welcomed

“Well let’s see,” Jackk started, trying to find a way to start off his story “My mom and dad divorced when I was a small filly and things were rough then,” Jackk explained, as a small frown started to form on his face “I also am- uh- Gay, and a lot of the school ponies either didn’t understand or just picked on me” he added

Winter began to frown as well, again, he doesn’t like ponies going through rough patches, “Well.. Just know i think its okay to be Gay, and no pony should say otherwise, everyone in Equestria should love and be loved” Winter said with a small smile on his face

The sentence caused Jackk to blush immensely as he chuckled nervously at the gesture

“Besides..” Winter reached his hoof out to comfort the other stallion “I’m kinda gay myself” he added with a giggle

Before Jackk could say or do anything the waiter soon brought their food to the table, and after setting down the silverware and napkins they trotted off

“Thanks!” Both stallions said at the same time as Jackk began to blush deeper from the action

Winter was the first one to dig in, grabbing his fork and quickly beginning to eat his salad, humming in delight as he hinted it was good

“What kind of stallions ya like?” Winter joked, of course the comment made Jackk blush even deeper as he gave off an annoyed look, trying to hide it by eating his burger

Winter scoffed though soon assuring; “i was joking” still, the quip made Jackk really flustered and he couldn’t help it either

The area between them laid silent in sheer awkwardness for each other, Winter was first to finish his food but Jackk was not even half way done

“You ok?” Winter asked with a concerned look to his face

“Sorta..” Jackk replied

“Did i do something?” the white pony asked as he frowned

“No.. just.. I hate looking back on life” Jackk added back, sighing deeply as he picked up the pace on his food

“Well just know that’s all in the past, we can only look forward and i see big things your way J” WInter replied with, gently touching the others hoof with his own

“I.. I know..” The grey stallion seemed to be a little more happier by the younger stallion’s words

“Whatcha say we spend this summer as friends? Just hang out occasionally during and after work!” Winter suggested

Jackk had to think about the offer, on one hoof it would grow his social abilities for the better, on the other he was already nervous enough as is

“U-Uhh.. Sure” He soon agreed, narrowing his eyes onto the other as a warm smile started to form

“Great! I can’t wait” Winter replied happily as he held the other’s hoof lightly in his own

“Ready to go?” Jackk asked

“Whenever you are” Winter said back

“Check please!” Jackk shouted once more as he let go of Winter’s hoof to gather his plate, once the check was placed on the table he signed it and got up shortly after

“Come on then” He said with a somewhat happy tone this time, and as Winter got up he soon trotted towards the exit

As Jackk walked out he tipped the waiter at the reservation desk a dozen bits or so, holding out the door for Winter the two would walk the same path down back to the white fluff ball’s place

The two walked down the even brighter streets (since Luna’s moon was out and brighter than ever) and as they did, Jackk seemed to be getting closer to the other, actually walking at a leisurely pace closer by his side

“I had a nice time..” Jackk said with a goofy smile as he nudged the stallion next to him

“Really? I’m glad ya did” Winter replied as they looked over the town’s illuminated glory, basking in its beauty

There wasn’t many words for the two as they walked, after all much was said between the two today, at least, more than what Jackk would say in one day, and that was saying a lot, considering he usually spent work alone without talking to any pony besides a few ‘Hello’s and ‘Goodbye’s from Patrons and a few quips back and forth at his boss

He was actually surprised he had such a time today, and part of him was excited to go home and ponder over it, and another part secretly wishes it to happen again

As the two walked down the cobblestone roads they soon reached Winter’s place, Winter walked up the pathway but Jackk didn’t

“Oh.. right”

Winter trotted back down the pathway to give Jackk a big hug “See ya tomorrow Boss” he said with a flushed smile

“See ya Winter, Goodnight” Jackk replied, and as he was just about to turn around Winter gave him a quick kiss on the cheek

And sweet Celestia did that embarrass him

Nevertheless though he went with it and smiled back, soon turning around and trotting back down Winter yelled “Bye!”

“Bye!” Jackk replied as they both waved at each other before parting ways

And as the larger stallion walked home, he rubbed his cheek occasionally while doing his usual overthinking tangent

“Oh Celestia, He’s adorable” He said to himself with an awkward chuckle

And as he soon reached home, and as they both relaxed and soon let Luna take their dreams off

He couldn’t wait, until the next day

• To Be Continued

Author's Note

Thanks SOOOO Much for reading! again please leave feedback and i hope this didn't leave ya on a cliffhanger