Warning: clueless, yet sweet Jack, a lot of fluff, Gabriel and Castiel are good uncles/father figures.
A/N: This is for @archiveofourown73‘s Blog Revamp Writing Challenge. This was a lot of fun to write; I never really wrote for Jack himself, so I hope did good.
Ever since Jack started living at the Bunker, he started to notice a few things. Every time (Y/N) was in the room, his stomach felt like it was fluttering or something. His cheeks would get hot and red in appearance when she'd smile his way. He'd get all shaky and stumble over his words when she was talking to him. He didn't know what was happening to him. So he went to ask Castiel for advice. He didn't want to ask her brothers in case they told her anything.
Jack found Castiel in the living room with Mary and the recently added Gabriel, who was recovering still from his ordeal with Asmodeus. He liked his uncle; he was a lot of fun and always had candy. When he came into the room, their conversation stopped.
“Hello Jack. What's the matter? You look lost,” Mary asked, standing up to approach the boy.
“But I'm not lost. I'm right here,” he stated, tilting his head in confusion.
“Oh no, honey. I meant that you looked like you needed help with something. Is there anything we can help with?” Mary simplified, bringing him over to where they were sitting. Mary took a seat next to him across from the angels.
“I think I'm getting sick. My stomach feels like it's fluttering or something. I get all shaky and my face gets red. Am I sick?” Jack explained, a little scared for their response.
He didn't expect Gabriel to start laughing. “Oh that's too cute! Jackie, does this happen when you're near someone in particular?” They all have an idea as to who may have him acting this way, but they need him to say it.
“Yes. Whenever I'm around (Y/N). I feel, vulnerable around her. Is this normal?”
“Oh, Jack. It's normal. What you just described, people tend to call it a “crush”,” Mary explained, gently squeezing the boy's hand.
“But I don't want to crush (Y/N). I feel like I want to hold her hand and be near her.” Jack was very concerned. Did these feelings mean something bad?
“Jack, a crush is used to describe having feelings for someone. It means you're in love with (Y/N),” Castiel simplified for him.
“And that's good, right?”
“Good? It's great! Our boy is growing up, Cassie!” Gabriel exclaimed dramatically, pretending to wipe tears away from him eyes.
“Ignore him, Jack. But yes, it's good. Have you tried telling (Y/N) how you feel?” Castiel asked, pushing Gabriel off of his shoulder.
“No, I haven't. I wanted to, but every time, my mouth goes dry and I can't say anything,” his eyes fell to his lap.
“You don't have to rush it, Jack. You can tell her when you're ready. Love isn't something to be rushed. I'm sure you'll know when the time is right,” Mary stated, wrapping her arm around his shoulders. She was right, but how will he know?
It had been two days since their conversation and Jack was wondering to himself how to tell (Y/N) when every thought faded. There was a singing...fish-woman...on the television screen, (Y/N) sitting on the couch. She seemed to be glued to whatever was on the screen. Jack found himself wondering closer to the couch, trying to understand what he was seeing.
“What is this?” he wondered out loud, startling (Y/N).
“Jesus! Oh Jack, you scared me,” she breathed a sigh of relief when she saw the you nephilim behind her, “it's a movie called “The Little Mermaid”. It's an old Disney movie.”
“Mermaid?” he asked, taking a seat next to her as she paused the movie before clicking a few buttons and bringing it back to the home menu.
“A mermaid is a mythical creature that has the top half of a woman and the bottom half of a fish. There are stories about them being good, being evil, or being more fish like than human. It's all strange, but to kids, mermaids are awesome,” she explained as the movie started up again.
Throughout the movie, Jack would ask questions and she'd answer. It was actually adorable how enthralled he was with the movie. Castiel and Gabriel were looking for them, but when they found them watching a Disney movie, they left them alone. But not without forging a plan to get the two together.
*The Next Day*
“I'm telling you Sam, it would be good for him to get out of here. Explore a little,” Gabriel bargained, watching as the moose of a man flip through books for any case references.
“I don't know, Gabe. I'd like for him to get out, too, but someone has to go with him,” Sam reasoned, looking up at the archangel.
“Well, duh! I'm not going to let him go out by himself. (Y/N) is going to be with him and Cassie and I are going to chaperone them.”
“So like a date?” Sam smirked, watching as Gabriel just realized what he said.
“Basically. I'm sure you two realized that Jackie boy has some feelings for (Y/N),” Gabe shrugged, sitting on the edge of the table next to the hunter.
“I have noticed. I've also noticed (Y/N) looking at him when she thinks no one is watching. As long as one of you is with them, I'm fine with it. Dean is a different story, though.”
Well, it took a little more convincing on his part, but when Jack had accidentally overheard that Gabe and Cas were taking him and (Y/N) on a day out on the town, he got excited. Too excited.
“Really?!” his joyful yell caught their attention and he suddenly found the ground fascinating as a blush spread across his cheeks. Whoops.
“Alright, they can go. Just keep an eye on them, alright?”
Everything was going according to plan. Gabriel took (Y/N) and Mary out shopping that day to get an outfit. (Y/N) didn't know why she needed a new outfit, especially a dress or skirt, but neither her friend nor mother were giving her any answers. While they were out, Cas planned a day with Jack, who took inspiration from the movie they had watched. Which worked perfectly because there was a festival happening at a nearby town alongside a river. It was perfect.
Percussion
Strings
Winds
Words
With the help from Mary, (Y/N) wore a dress similar to Ariel's blue dress from the village. Her hair was pulled back into a braid with a blue bow and just a little makeup. Jack wore a simple white button down shirt and a nice pair of slacks. Gabriel drove them to the town where the festival was happening and let them wonder around while he and Cas watched from a distance.
There you see her
Sitting there across the way
She don’t got a lot to say
But there’s something about her
And you don’t know why
But you’re dying to try
You wanna kiss the girl
They had sat down for some lunch, talking and enjoying the music around them. But Jack kept thinking about the movie and how to tell the girl across from him how he felt. And right now, he wanted to kiss her, but he didn't know how. (Y/N) wasn't the one who didn't have a lot to say; it was him.
“Hey Jack. Wanna go see the horses over there?” she suggested, pointing over in the direction of a carriage ride down the street.
“S-Sure. I'd like to,” he agreed, allowing (Y/N) to pull him down the street towards these massive, yet gentle beasts. He almost didn't know she was holding his hand until they came to a stop by the carriage.
“Well hello there! Would you two like a ride?” the carriage man asked, smiling at the couple. Jack looked behind him towards Cas and Gabe, who gave him a smile and the go-ahead.
“Yes, we would. Thanks you,” he replied, helping (Y/N) into the carriage before climbing in after her. He thought his uncles were joining them, but they took a seat on a bench to wait for them.
Yes, you want her
Look at her, you know you do
It’s possible she wants you, too
There is one way to ask her
It don’t take a word
Not a single word
Go on and kiss the girl
It was so peaceful, watching the horse trot along as the driver explained some of the sights around them. He was just as amazed by everything as (Y/N) was; both of them taking in everything. Jack looked over at her as she gave a laugh and waved back to some children who waved at them. When she turned back around to look at him, Jack smiled and looked at his lap, a blush working it's way onto his face. If only he knew how (Y/N) felt about him; especially when he got shy like this. Both wanted to say the words, to give a sign that they liked each other, but they couldn't. Not yet.
The carriage returned to the spot they took off from and they disembarked before finding their guardians. The two angels took them down the block, stopping at a few stores and booths along the way. Jack had found this lovely mermaid necklace ironically and asked Castiel if it would be perfect for (Y/N). With a smile, Cas pulled put a five dollar bill and handed it to the vender, who wrapped it up for him. Meanwhile, Gabriel was trying to get (Y/N) to buy some candy for Jack, but she knew what she was looking for. A seashell bracelet.
They continued walking before (Y/N) let out a small squeal of excitement. There was a dance happening at the end of the street. She grabbed Jack's hand and tried tugging him over to where the others were at.
“C'mon Jack! Let's dance!” she pleaded as she got him moving.
“I-I-I don't know how to though,” he confessed, but she smiled nonetheless.
“I'll show you.”
Sing with me now
Sha-la-la-la-la-la
My, oh, my
Look at the boy too shy
He ain’t gonna kiss the girl
Sha-la-la-la-la-la
Ain’t that sad
Ain’t it shame, too bad
You gonna miss the girl
Getting him to the dance floor was easy enough. Actually getting him to dance, a whole new problem. Jack shyly looked around at the other couples and tried to figure out how to copy their moves, but almost tripped over his feet trying. (Y/N) steadied him and took one of his hands.
“Like this. Place this hand on my hip,” she stated as she manipulated his hand into place, “and this one,” lifting his free hand, “holds mine like this. See, not so hard. Now, just follow my lead. I know, the guy's supposed to lead, but just follow me and let the music guide you.”
“How?” he tilted his head to the side as they slowly begun to move to the music.
“Just don't think about the movements. Just enjoy the moment and before you know it, you'll be dancing.”
Cas and Gabriel watched from the sidelines as (Y/N) taught Jack how to dance. Some of the other couples and families watching couldn't help but smile at Jack's shyness and (Y/N)'s patience with him. One woman said it was cute seeing him look so in love with her. She wasn't wrong though.
Jack was having the time of his life dancing with (Y/N). Her laughter made his chest flutter as he successfully twirled her around. He was getting the hang of this. Now if only telling her was as easy as this.
Now’s your moment
Floating in a blue lagoon
Boy, you better do it soon
No time will be better
She don’t say a word
And she won’t say a word
Until you kiss the girl
Somehow they ended up in a little row boat on the river. (Y/N) offered to row it, but Jack took the oars himself and rowed them to a little secluded lagoon not too far from where they started. There was a large willow tree with these beautiful white flowers dangling around them. It was so peaceful.
Jack was happily asking questions that (Y/N) had no problem answering. But internally he was fighting with himself. If he didn't say anything soon, it would be too late. (Y/N) will never know that he liked her.
Having seen this as a possibility, Gabriel told Cas “I'll be back” before disappearing. Castiel could only sigh as he had an idea to what his brother had in mind. He didn't bother going after him. Castiel was smart enough to not get dragged into Gabriel's schemes. Well, he was now.
Gabriel shifted into a blue bird that sat on a branch above the two. He could see them holding hands as they talked, but letting go after a moment. “Time for drastic measures.”
Sha-la-la-la-la-la
Don’t be scared
You got the mood prepared
Go on and kiss the girl
Sha-la-la-la-la-la
Don’t stop now
Don’t try to hide it how
You wanna kiss the girl
Sha-la-la-la-la-la
Float along
Listen to the song
The song say kiss the girl
Sha-la-la-la-la-la
Music play
Do what the music say
You wanna kiss the girl
Gabriel started singing, sparking up other birds to start singing as well. Well, there were a lot of whistles and chirps. He was actually singing.
“Did you hear that?” Jack asked, looking around for the voice. (Y/N) only smiled and shrugged her shoulders. In all honesty, she did hear Gabriel singing, but didn't say anything. Watching as Jack tried to find his uncles voice but couldn't.
“Jack, hey. Is there something you wanna tell me?” she prodded, taking one of his hands in hers. He looked at her in shock, eyes wide as he scratched at the back of his neck.
“Um...yeah...there is. (Y/N) I...”
“Yes?”
You’ve got to kiss the girl
Why don’t you kiss the girl
You gotta kiss the girl
Go on and kiss the girl
Gabriel watched, smiling at how shy his nephew was. (Y/N) was perfect for him.
Jack let out a small sigh before taking (Y/N)'s free hand, rubbing a thumb over her hand. He knew what he wanted to say, but nothing was coming out. He was at a loss. Until (Y/N) got his attention.
“Jack?” He met her eyes, head tilting slightly in confusion. (Y/N) gave him a small smile before leaning in slowly. Jack slowly leaned in to meet her, but stopped short. Was this okay?
Any negative thoughts left his mind as (Y/N) placed a small, gentle kiss to his lips. She pulled back a little to give him a chance to respond. His response was leaning forward again and captured her lips in a sweet, yet shy kiss. Gabriel took that as his cue to leave, returning the Castiel's side.
“I take it went well?” he asked, already knowing the answer by his brother's grin.
“Yep. Now we just wait for them to return the boat. I knew this was going to work!” he boasted, a smug grin on his face.
“Actually, this was my idea. You just went along with it,” Cas deadpanned, choking on his laughter when Gabriel gave him a heat less glare all while mumbling under his breath about “disrespectful little brothers”.
Jack had rowed the boat back to the dock before getting out as the dock master moared it to the post. Offering his hand, he helped (Y/N) out of the boat and they walked hand-in-hand over the where the angels stood.
“Did you too have a good time?” Castiel wondered, taking notice of their intertwined hands.
“Yes, we did. It was a lot of fun!” Jack exclaimed, jumping a little with joy. (Y/N) laughed at his happiness before turning to Gabriel.
“Nice singing, Gabriel.” Her honesty shocked him as he floundered trying to cover up what he did. Jack didn't notice as he was talking to Castiel about something.
“How did you...?”
“If you were trying to only let Jack know, next time, use angel radio. You projected. But thank you.”
Gabriel couldn't help but laugh as he shook his head. (Y/N) was definitely a smart cookie. And a perfect match for his nephew without a doubt. By the days end, the four of them made their way home. (Y/N) and Jack had fallen asleep in the back off the car, their hands connected as (Y/N) laid her head on Jack's shoulder, his head resting on hers.
It would take a little convincing on her part to get her brothers to let her be with Jack, with a little help from Mary. But it won't be too hard once they see the two of them dancing around the living room to another movie soundtrack. The seashell bracelet standing out on Jack's wrist as the light bounced off of (Y/N)'s mermaid necklace.
While he might not have made the first move, he definitely got to kiss the girl.
