A/N: So...I don't know if anyone from the HSM era remembers me, but I'm back! Having started a different story a while back and then left it unfinished, I didn't want to start another for Troy & Gabriella until I was sure I could complete it. So here it is, a multi-chapter AU where each chapter takes the form of a date. Please let me know your thoughts if you read it. Thank you!

Dates

Chapter One: First Date

This was a bad idea, Gabriella Montez mused as she waited in the foyer of the restaurant for her date. No good can possibly come out of agreeing to go on a blind date after you've just had the day from hell.

When Sharpay had called and told her she had something that would cheer her up, this certainly hadn't occurred to her.

Besides all the standard awkwardness of going out for dinner with someone you didn't know, there was having to get all dressed up when you'd rather just stick your PJs on and order a takeaway.

But still, against her better judgement and because she knew that her best friend meant well, here she was waiting for Mr Five-Minutes-Late.

"Are you Gabi?" An attractive, sandy blonde-haired man had approached her.

She nodded, feeling strange about the whole scenario.

"I'm really sorry I'm late. I'd tell you why but given that we've only just met I think that's an explanation best saved for later. It's sort of complicated."

As long as it's not that you're married, Gabi thought, thinking about all those people whose Facebook relationship statuses read 'It's Complicated'. A public way of telling the world you were taken, but that you could also be single again at the drop of a hat.

She pushed her doubts to the back of her mind and smiled at the man. "It's fine. Yes, I'm Gabi. And you're..."

He frowned, "Sharpay didn't tell you my name? Wow, this must've been weird for you - waiting to meet a nameless stranger! I'm Troy," he added after correctly guessing her thought process so far.

"Yeah, she didn't tell me anything but knowing her I expected nothing less." Gabi rolled her eyes as she described the impulsive blonde. "So, Troy. Shall we get a table?"

They approached the woman at the front desk and were quickly escorted to a table for two.

While a waitress disappeared to see to their drinks orders, Gabi sat opposite Troy in silence, wondering what to say next. She was usually more outgoing than this but her bad day had left her feeling flat.

"Well," Troy began with a soft smile. "I hope you won't judge me on my lateness. I'm normally early for everything, I promise." he raised his hands in a comical display of defence, and Gabi laughed.

"I believe you," she replied, the stress of the day slowly starting to melt away. "So how do you and Shar know each other? Like I said, she didn't tell me a thing about you."

Her date looked down at the tablecloth as the waitress placed their drinks in front of them and handed them each a menu. Once she had left them to it, he slowly returned his gaze to meet Gabi's eyes.

She sensed that there was a story attached to whatever his answer would be.

"We met through work," he said quietly.

"Oh!" she smiled. "You're a doctor?" She wondered why her friend wouldn't have told her that. Sharpay worked as an admin assistant at the local hospital, and was dating one of the doctors there herself.

Troy rubbed at the back of his neck. "No. Actually I'm an estate agent. I met Sharpay at the hospital when I was visiting someone. My sister. She's been ill..."

Recalling that Shar worked on the Oncology department, Gabi found that her heart sank for him. Cancer.

"That's awful, I'm so sorry to hear that. What's your sister's name?"

The troubled look in his eyes subsided for a moment. "Karen. She's sixteen. I'm all she has; we're all each other has, really."

Wow. Although she wouldn't dream of prying into his sad statement, she wanted to hear more.

"That's why you were late meeting me," she said instead, her tone gentle.

"Yes. That's why I was late. Sorry again."

"God!" she replied quickly, horrified at herself. "Don't be! Honestly, if you could have heard me earlier today, moaning about my day at work like it was the worst thing in the world..."

Gabi shook her head, having put life into perspective in the time it had taken Troy to brief her on his situation.

"What is it you do then, Gabi?"

"I work with children, mainly. Social worker," she explained. This seemed to spark an interest in him, and she talked a little about the job while they chose from the menu.

When she grew sick of the sound of her own voice, Gabi asked Troy about his own work, and by the time their meals arrived she felt like she knew all the ins and outs of selling houses. And she hadn't found it boring.

Attempting to cut into the chicken she had just been served, she groaned. "This is overdone," she said with a sigh. "I don't think I could eat it."

Troy put down his cutlery. "Mine's not even warm."

"Ah...to the chip shop instead?" she suggested, and he nodded, catching the eye of the waitress to explain why they wouldn't be paying for their very questionable dinner.

"Fish and chips," he remarked as they sat at one of the little tables inside the nearby chippie a short while later. "You may as well have read my mind."

Gabi grinned. If they'd met here instead of at the restaurant she mightn't have felt the need to go to all that effort with her outfit. Which would have been fine by her.

"How about we do this again next week?" Troy asked after they'd eaten.

She suddenly realised that her 'day from hell' now seemed like a distant memory.

"You're on."