Troy pulled up to the hotel. He got out and walked around to hand the keys to the valet when he spotted her. The glass doors of the hotel slid open, and she walked out like a model off a runway. She wore a blue a-lined flower-patterned dress that stopped around mid-thigh. It showed off her long-tanned legs. She wore simple, low heeled beige wedges that paired nicely with her crossbody bag. Her hair was down in it's incredible curls and her make up was light and natural as always. She looked stunning, and he had half a mind of dragging her back upstairs.

"Is this too much?" Gabriella asked nervously, bringing Troy back to reality. She changed her outfit four times before settling on this.

"You look beautiful," he replied and kissed her on the cheek. "Ready to go?"

She bit her lip to conceal a smile and nodded hesitantly. He stepped back and opened the passenger door for her, admiring her beauty as she got in so gracefully. Once her door was shut, Troy jogged around to the driver's side and hopped in. As he started the car, he noticed her bouncing leg and her fingers fiddling around with the hem of her dress. He took her hand and kissed the back of it.

"They're gonna love you sweetheart."

God I hope so.

Gabriella watched the scenery pass by, her nerves growing by the second. "Okay… crash course," she said, needing a distraction before she threw up, "you have five siblings."

"Mmhmm… one brother and four sisters."

Jesus. She racked her brain, trying to remember every conversation they had about his family, but kept pulling up blanks. Maybe it was her anxiety. All she could remember was that his parents were still happily married and that he wasn't an only child. She planned to review any photos he had of the family on Instagram, to put faces to the names, but she simply ran out of time. "I know Sharpay is your younger sister."

The car stopped at a red light and Troy looked over at her. "Yeah, so Andrew is the oldest… then it's the twins, Martha and Mary-"

"Are they identical?"

Troy thought about it for a minute and the light turned green. "Yes, but Mary is blonde now so they're easier to tell apart. Oh! That, and Martha has some baby weight."

"Troy!" Gabriella laughed in disbelief. "You can't say that."

"What? She's my sister… so it's okay." Gabriella rolled her eyes and shook her head. Doesn't matter if a woman is related to you or not. You don't mention her weight. "Anyways, then there's me, Sharpay and baby Kelsi."

Gabi's brows furrowed in confusion. She could've sworn that Kelsi was about her age. "Why do you call her baby Kelsi?"

"Because she's the youngest and can do no wrong."

Gabriella watched as Troy merged onto the highway so effortlessly." What are they like?"

His eyes dart around the mirrors and the road before switching lanes. "I don't know," he said with an embarrassed chuckle. He wasn't sure how to explain what having siblings is like. Gabriella grew up as an only child, and any cousins she had were much older and scattered across the globe. "I guess… they're nosy and noisy, and sometimes I wished they were never even born. But I love them and they're my best friends… and honestly, I wouldn't trade them for anything in the world." He glanced at her, "Obviously if you tell them I said that I'll deny it to my grave."

Gabriella giggled lightly as she digested what Troy said. She never really had time to wonder what life would be like if she had a sibling. Being a 'child prodigy', she never had time to miss out on something she never had in the first place.

"And what about your parents?" Gabi asked.

"They're nice people… dad's a hard ass, but I guess someone had to be." Troy glanced her way, "My mom is the sweetest person you'll ever meet."

Gabriella smiled softly and looked back out the window. Her nerves weren't settling. Troy gave her an idea about his family, but she still didn't know anything about them. She started to wonder if this was a good idea at all. But then again, when would be the right time?

Her ears picked up on the sound of the blinker and the car veering slightly towards the highway exit. Her leg started bouncing like crazy and her mind created all sorts of scenarios. What if they didn't like her? What if they don't think she's the one for Troy? Would they make him divorce her? A lump formed in her throat at the thought. Would he divorce her if they asked him to?

The car slowed down to a stop and Gabriella's pulse began to race. She got out of her head and realized they were sitting at a red light. They weren't there just yet. Troy reached over for her hand and gave it a light squeeze.

"Trust me babe… just be yourself, and they're gonna love you."

The black Audi pulled up to Troy's childhood home. Gabriella has seen pictures, but it didn't do the house justice. It was beautiful, like a photo in an architecture magazine.

Troy shut off the engine and turned to Gabriella. "Fair warning… my parents and Andrew, you don't really have to worry about… it's my sisters."

Gabi gulped. "Your sisters?"

Unfortunately, Troy didn't elaborate and got out of the car. He ran to the other side and opened her door for her. He helped her out before opening the backseat and grabbing the bottles of wine.

Gabriella stood beside the car just staring up at the house. I'm gonna be sick.

The front door opened, and an older woman stepped out. Her blonde hair was clipped out of her face. She wore a purple paisley patterned blouse with cropped white pants. Gabriella guessed this was Troy's mom. She was fetching. There was no way this woman had six kids and they're all grown.

Troy placed a hand on the small of her back and whispered, "I love you and you're amazing."

Just like this morning, Troy's mother met the couple halfway. "Oh Troy she is stunning!" She shrieked and pulled Gabriella into a hug. The younger woman tried not to freak out. She's not into the habit of hugging people within the first few seconds of meeting them. Lucille held the girl at arm's length. "It's nice to finally meet you!"

Gabriella laughed nervously. "Hi… it's nice to meet you too Mrs. Bolton."

"Oh please darling, call me Lucille. Come on in… are you hungry?"

Gabi plastered a smile on her face and somehow managed a slight nod, despite the butterflies in her stomach. Lucille looped her arm with Gabriella's and led the woman inside. She looked back at Troy with panic in her eyes, making the man chuckle to himself.

Gabriella marveled at the interior. It was just as gorgeous as the outside. It was so homey - a vast contrast to where she grew up. Gabriella's childhood home was much larger than the Bolton residence, but it always felt more like a museum than a home.

Gabriella's eyes landed on two very tall gentlemen sitting on the couch. They looked a lot like Troy, but the younger one had brown eyes and a bigger build.

"Gabriella, this is my oldest, Andrew and my husband Jack." The gentlemen stood up and shook hands with the girl. Another man walked in from the other room with a beer at hand. "Oh! And this here is my son-in-law, Jason - he's married to Martha."

Gabriella gave the guy a tight-lipped smile and a small wave of her hand. Shortly after Jason appeared, two women similar in stature walked in from the kitchen. Their identical faces told Gabriella exactly who they were.

"Martha! Mary! This is Troy's wife, Gabriella."

The twins didn't even try to hide their displeasure. They did not look so thrilled to meet the new addition to their large family. But they gave a polite smile and a short wave before immediately scurrying back into the kitchen.

The sound of feet coming down the stairs made Gabriella and Lucille turn around. The dark brunette let out a little sigh of relief when her eyes landed on the one person she kind of knew.

Lucille was about to introduce Gabi to the youngest Boltons when the girl beat her to the punch, "Sharpay…" she greeted and the pair hugged instantly, throwing everybody off. Sharpay wasn't the hugging type at all. She always dodged them if she saw them coming. "How are you feeling?"

"Much better… nothing like a power nap and a nice shower. By the way, I have your top upstairs."

"Oh you can keep that."

"Are you sure?"

"Yeah I have dozens of others just like it."

"I didn't know you two met each other already," Lucille interrupted, breaking up the mini reunion.

Without thinking, Gabriella said, "last night actually."

"Oh?" Gabriella felt a shift in the room. Did she say something wrong? She looked around at the uncomfortable faces of everyone present. Lucille clasped her hands together, wringing them slightly. "Well… I'll go check on the twins. Make yourself at home." And with that she disappeared into the kitchen with Jack and Jason in tow.

Gabriella looked at her husband and Sharpay, a little unsure of what just happened. "She didn't know you got here yesterday," Sharpay explained, "nor that we hung out last night either."

Well… that's just… great. Gabriella glanced offsides and peeped at the only Bolton she wasn't formally introduced to. "Hi I'm Gabriella."

The young woman grinned. "I'm Kelsi," she said and just like her mother, she pulled Gabriella into a hug. Gabi was a bit taken aback but welcomed it anyways. "Would you like a tour of the house?"

"Sure." Troy watched as Kelsi and Sharpay led Gabriella upstairs. He knew she'd be in good hands. Now that the shock was over, Troy went into the kitchen where everyone was hiding out.

Whatever they were talking about died the second Troy appeared. "Alright… say your piece." The men looked around at the women who busied themselves with the food. Jack and Jason quickly grabbed the meat for the grill and practically ran out of there. "Kelsi and Pay are showing her around, so you got like two minutes."

Mary stopped what she was doing and looked at Troy exasperated. "What are you doing with her Troy? You know, I never figured you'd be the type to sleep your way to the top. You're smarter than that."

"Excuse me?"

"Jason filled us in on who she is… honestly Troy, what were you thinking," Martha asked.

Troy rolled his neck. "It's not like that. I-" but Troy didn't get the chance to defend himself when the girls entered the kitchen. "Hey… let's go."

"Troy-"

He was tempted to leave; just get in the car and drive off. But he also wanted them to get to know her. It wasn't fair of his family to write them off like that. They don't know anything and that was something he was wanted to change.

But as he looked at the perplexed faces of his younger sisters, Troy decided they would stay. He took hold of Gabriella's hand and led the way through the dining room to the back patio where a long dining table was set.

"Is everything okay?" Gabriella asked quietly.

"Yeah…" Troy said stiffly, "let's get this lunch over with and head back to the hotel."

"You can sit next to me," Kelsi said and gestured to a brown wicker chair. Gabriella smiled with a nod, trying not to seem overwhelmed. She wondered what they were talking about before they walked in. Clearly it was about her.

Troy poured his wife a glass of red wine, which she graciously took a sip. She couldn't shake this nagging feeling that she has overstayed her welcome.

As Troy took his seat, the twins and Lucille came out with the salad and a few side dishes. Sharpay followed suit with the condiments.

"So Gabriella," Jason started - and of course he would - "what's it like being the youngest Vice President in tech history?"

Looks like someone did their homework. The curly haired brunette took another sip and cleared her throat. "Well… no one takes you seriously."

"I'm sorry, you're a VP? How old are you?" Sharpay asked they took their seats. The woman looked no older than she was. Still, to be a Vice President of a company as large as Montez Inc. at twenty-five, it was pretty impressive.

"I just turned twenty-one in December," Gabriella answered.

The older Bolton members raised a brow at Troy, and this didn't know unnoticed by Gabriella. Was their age difference that much of a concern? Internally she sighed. There goes strike two.

"That's insane! What are you - a genius or something?"

Gabriella blushed. "Or something..."

"So how did you and Troy meet?" Kelsi asked.

Gabriella glanced at Troy, the blush on her cheeks reddened even more. Troy laughed lightly and decided to answer for her, "we met at a company retreat… that I kinda crashed."

The youngest Bolton's brows furrowed in confusion. "How can you crash a company retreat?"

Three years ago…

The sign read: No Cellphones. No Laptops. No Tablets or Smartwatches.

Troy peeled his eyes away from the sign and looked around at the large white canvas tents. He was instantly regretting this decision. He didn't want to seem lame in front of his new coworkers, so Troy took them up on the dare. They bet him $500 that he wouldn't last the weekend. The way Troy saw it, it was easy money.

He looked around some more, trying to figure out where to go. Then she came up to him. He couldn't help but check her out. She was wearing black biker shorts and a teal t-shirt that read 'Montez Inc. Wellness Retreat'. Her long dark hair was up in a ponytail, underneath a gray baseball cap. She wore white running sneakers and held a clipboard under one arm.

He dropped his bag on the floor. "You're not Helen," Troy said when she was close enough.

Gabriella giggled and it was like music to his ears. "No I'm not… I'm Gabriella," she said, and they shook hands, "Helen had an emergency last minute, and no one else could fill in. And I owed her a favor…"

Troy smirked. "A favor..."

Gabi blushed. "So do you need help checking in?" Gabriella asked and pulled out the clipboard.

"Y-yeah… Bolton comma Troy."

"Is that how you always say your name Bolton comma Troy?" Troy's ears turned red hot and he stuck his hands into the front of his jeans. He watched as she turned the paper over and frowned. "I'm sorry Bolton… I don't have you on my roster. Did you sign up last week?"

Troy sighed. "No actually, I just started Monday… I must've heard Helen wrong. She mentioned the retreat, and I thought she took care of it."

Gabriella brows furrowed. That doesn't sound like Helen. She was super meticulous about everything. She gave Gabriella an excel sheet with the hour-by-hour plans for the whole weekend that Gabi must follow like it was her bible. She made sure Gabriella had not only the PDF versions of the sign-in sheets and the forms, but hard copies as well.

It wasn't that new hires weren't encouraged to go to the retreat. It was just Helen knew this retreat was specifically for the software developers and engineers in her division. Gabi knew this guy before her wasn't one of hers. She would remember if a guy who looked like that worked for her. Now Gabi wasn't necessarily judging Troy, but he didn't look like he knew the difference between a stack and queue.

"Helen said she'd take care of it? Or do you mean Henry Cliff?" Every year that man did this act with a new hire. Most of his division thought the wellness retreat was a joke. It was funny the first time he did it, but now it was just sad and annoying.

Troy gulped and tried to keep his cool. He couldn't possibly be fired for this could he? He decided to fess up. No dare is worth losing his job. "The guys bet that I wouldn't be able to make it through the weekend."

Gabriella pursed her lips in thought. At least he confessed. He was cute and a newbie. He clearly had no idea who she was. "How much are they betting you?"

"Like five hundred."

Gabi smirked. "Okay… I'll let you stay. But you have to participate in everything."

"Really?" He couldn't believe it. She's going to let him stay.

"Mmhmm… oh! And we split, fifty-fifty."

"Deal." They shook on it. Troy picked up his bag and followed Gabriella towards the tents.

She pulled back the flap and they entered the tent. It was a lot different than Troy imagined. It had a bed with pillows and blankets. There was a side table with a lamp and large pillows to sit on placed atop of an accent rug. This was no ordinary camping retreat.

"You're lucky Dean had the flu and couldn't make it."

'Thank you, Dean,' Troy thought.

"Not only was it a wellness retreat, but it was also all about team building. One of the requirements was that you had to partner with someone you barely knew or had some tensions with. We were partnered because we were the last to show up… and I guess you can say the rest is history," Gabriella said as she looked up at Troy. He looked down his nose at her, and they smiled like they were the only ones in the world. They shared a quick peck on the lips, making Sharpay and Kelsi giggle quietly.

Martha hated to admit it, but their story was so much cuter than hers and Jason's. Like most couples in this day in age, Martha and Jason met online. They dated for about two years before Jason popped the question. Now here they were, five years in with a 6-month-old son. She was slightly jealous of them. She always wanted a cute meet. But what impressed Martha most about Gabriella was that she could've ripped Troy a new one, but she didn't. That says a lot about her.

Mary, on the other hand, was too distracted noticing all the little things this couple did as they retold their first meeting. She couldn't help but observe the way Gabi leaned into Troy. Mary watched how his arm rested behind her on the chair, and occasionally, his fingers brushed up against her shoulder. No one saw the way her hand slowly made its way onto his lap, and hopefully Gabi was just holding his other hand. Her smile made him smile.

It was gross to watch.

Mary wondered who this man was sitting before her. Troy was never this affectionate with any of his exes. He gave them hugs and sat squarely beside them. They would mostly bump elbows. If they were lucky, he'd give them a kiss on the hand or on the cheek. But the Bolton siblings all knew it was a show for their parents. Mary knew for a fact he wasn't a saint. After all, voices carry in the locker room.

Jack came over with a large platter of sausages, burgers, steak, and chicken. "Alright guys… dig in."

As they filled their plates, Kelsi asked, "so how did you meet Grandpa John?"

Gabriella and Troy shared a look that was indecipherable. Gabriella blushed again and tucked a strand of hair behind her ear. Troy resisted kissing her and took a sip of wine instead. Troy cleared his throat, "He uh… walked in on me proposing and ended up officiating our marriage."

"Shut up!"

Andrew made a face. "I didn't know Grandpa John was an officiant."

Martha frowned and asked her husband, "Why didn't we have him solemnize our marriage?"

"You invited Grandpa John but not us?" Lucille's voice cut over everyone else's.

Everyone looked at Troy, making him rub the back of his neck nervously. "We didn't actually invite him. He kind of just… showed up."

Two years ago…

It was late May and Grandpa John decided to pull a 'Everybody's Fine' on his four grandkids who moved away and don't make it home that often. His trip started with Charlotte in New York, and then Anthony in North Carolina. He visited Lisa in Iowa and his final stop was Troy in California. Unlike the film, every one of his grandkids were doing fine.

While at the airport in Iowa, Grandpa John called Troy's office. He wanted to make sure Troy was still in LA. The last thing he wanted was to show up and he was gone. That almost happened in New York with Charlotte.

His assistant answered the phone. "Hi, I was wondering if I could speak with Troy… is he available?"

"May I ask who's calling?"

"It's his grandpa - John Bolton."

"One moment…" Grandpa John waited patiently as his foot tapped along to the holding music. It wasn't that long until his assistant came back, "Mr. Bolton-"

"Please… call me Grandpa John."

"Grandpa John… Mr. Bolton will not be in today. Would you like to leave a message?"

Grandpa sighed. "No that's alright. Does he have another cell phone number? We made plans, but he's not picking up his phone and I'm already at the airport. He didn't send me his address. Ya know? He's still in town, right? He said he'd be home."

"Aww… oh Grandpa John… umm let me see what I can do." He was put on hold for another few minutes. "Okay Grandpa John… if Mr. Bolton asks, you never got this from me," she sighed heavily as she clicked around, "I miss my Pop Pop every day."

"I'm sure you make him proud."

"Thanks," she said lowly and then perked up, "okay… looks like Mr. Bolton will be up at the beach house this weekend. Would you like me to text you the address?"

"That would be wonderful… thank you umm…"

"Cindy."

"Thank you very much Cindy."

"You're very welcome Grandpa John."

After a three-and-a-half-hour flight, and a long, expensive cab ride, Grandpa John was walking up the winding path to the beach house. The gate was surprisingly open, and he followed the music to the back patio. He stopped suddenly at the sound of his grandson's voice.

"-I love you and I can't picture my life without you… will you marry me?"

Gabriella let out a breathless 'yes' and the pair shared a kiss that had so much love in it. Grandpa John smiled as Troy twirled his fiancé around and gave her a big hug.

"I'm sorry I don't have a ring yet… I wasn't really planning on proposing today."

Gabriella giggled and kissed him once more. "We should get married tomorrow," she joked.

"Today, tomorrow, six months from now… a year - I don't care baby as long as it's me and you."

"How about right now?"

The couple whipped around. "Grandpa!" Troy exclaimed and jogged over to the older gentleman. The Bolton men embraced tightly. "What are you doing here?"

"Well… last time we talked, you said Memorial Day weekend… so I booked a flight, and here I am."

Troy chuckled, shaking his head lightly. He vaguely recalls the conversation, but he definitely did not tell him to fly out.

"How'd you find me?" Grandpa John zipped his lips, locked it, and threw away the key. "Cindy…"

"I plead the fifth." Grandpa spotted Gabriella behind Troy, sipping on a glass of wine. "And who is this beautiful young lady?"

Troy beamed and led his grandfather over to his fiancé. "Grandpa John, this is my girl- sorry… my fiancé Gabriella. Gabriella, this is my grandfather."

Gabriella smiled bashfully. "It's a pleasure to meet you Mr. Bolton."

"Please darlin' call me Grandpa John." He opened his arms, and she welcomed the hug with a giggle. "I hope he's been behaving himself," he said as he turned towards Troy with a raised brow.

Gabi giggled as her fiancé rolled his eyes. "He's been nothing but a gentleman."

Grandpa gave her hand a nice squeeze. "Good."

"So grandpa you must be starving," Troy said and grabbed his grandfather's suitcase.

"Eh… I can eat."

Troy led Grandpa John into the beach house to show him around and where he'll be staying. Meanwhile, Gabriella headed towards the kitchen to prepare a light lunch.

The three of them sat outside on the patio under a fancy looking awning, draped in white. Lunch was delicious and the wine was lovely. After all that traveling, Grandpa John was in heaven. The weather was perfect, and the view of the beach was stunning. He has never seen anything like it. He sipped on the white wine and looked over at the doting couple, so happy to see them happy.

"You know I was serious about the offer… you guys could get married today, if you'd like."

Gabriella and Troy exchanged a look. "Really?"

"Of course… I got certified to be an officiant a while back… what can I say? I'm a sucker for love."

Troy and Gabriella looked at each other again, excitement dancing in their eyes. "Do you want to?"

"Do you?"

After what seemed like forever, they turned back to his grandfather. "Yes… let's do this."

Grandpa John smiled. "Fantastic… okay we're gonna need some rings and a pair of witnesses or a witness."

Gabriella looked up at Troy. "Well Taylor and Zeke should be here soon."

"And I know where I can get some rings," Troy added.

"Excellent… Troy why don't you and I go get the rings so Gabriella can get ready."

Two hours later, Troy stood beside his grandfather on the beach under an arch that they found in the garage. With Zeke's help, they managed to bring it down to the beach and decorate it with white chiffon curtains and flowers they got at a nearby florist.

Troy shifted his weight nervously. He wasn't getting cold feet. He was more excited than nervous. He just hoped that Gabriella still felt the same. If she changed her mind, he'd respect it. He would never make her do anything she didn't want to do.

But there she was. Gabriella descended the stairs to the beach and instantly took his breath away. She wore a high neck chiffon crop top that crisscrossed around the back into a neat bow. It matched the billowing maxi skirt with a slit that stopped right below her hip. She looked like a goddess.

When she was close enough Troy offered her his hand and led her to his grandfather. Gabi gave her bouquet of flowers to Taylor to hold and faced her soon to be husband.

'I love you,' he mouthed to her.

'I love you,' she replied in the same manner.

Grandpa John looked at the couple before him and smiled softly. He took a deep breath and began, "Beautiful people… we are gathered here today, in the presence of witnesses, to join Troy Bolton and Gabriella Montez in matrimony…"

Hey guys! Hope you liked this little backstory of how Troy and Gabi met, and more importantly - how Gabi met Grandpa John. Let me know what you think :) -M