Disclaimer: I don't own High School Musical.

Summary: What's a single woman to do when she trips, literally, over her now homeless, former high school crush, the basketball superstar himself, Troy Bolton? She decides to pluck him from the streets and help him rebuild his life. TroyGabriella.

Back story: It's a bit AUish. But Gabriella did transfer to East High. She was still the brainiac and Troy was still the basketball captain. They shared some classes. But they never sang together, so they don't really know each other. Original, no? (Sarcasm was intended) Oh, and by the way, I've also changed that Gabriella did pre-med instead of pre-law.


If one were to ask me, Gabriella Montez, at age eighteen, where I would be ten years later, I'd proudly answer that I'd have graduated medical school and, without hesitation, I'd say I would be starting an internship with my best friend Taylor at my side. And I would have moved out of my mother's house by then and maybe I would live in a nice apartment with a nice, friendly cat to come home to.

And ten years later, this is exactly where I'm at.

If one were to ask me, Gabriella Montez, at age eighteen, how my love-life would be ten years later (which my mother usually did as she only had one child: her only hope of having grandchildren), I'd sputter and try to change the topic while my face turned a lovely shade of tomato red. Because you see, at age eighteen, I still had never been kissed or asked out by a boy before. Boyfriends would only interfere with your studies. That was my motto—or at least it was whenever a snobby cheerleader asked who my date to prom was.

And ten years later, I find myself wishing I could shake some sense into that eighteen-year-old version of me for not getting any experience with the opposite sex, because now, sitting in a quaint restaurant, across from my blind date, I have no idea what to do. I feel clueless and out of place. Yet if I had gone on a couple dates as a teenager, everyone else would have been just as clueless and out of place as me, and I wouldn't be feeling like an amateur swimmer in a pool of Olympic candidates like I am right now.

The gorgeous Italian model, who Taylor had set me up with, begins droning on about his skin care techniques, "While I prefer shark oil essence, a friend of mine is convinced natural bee mucus extract is the best choice. What do you think?"

"Um, I watched the Discovery Chanel once, and found out there are these sharks that produce gallons of thick, slimy, overall just disgusting mucous which they use to trap the food they eat. Is that what you use?" I ask.

Choking on the low-calorie salad he ordered, my date manages to reply, "I don't—I don't know, but I think it does wonders for my skin."

"That's...good. Your skin does look nice."

Another moment of awkwardness passes between us. It's the twenty-second one this evening, I note.

Perhaps this whole dating thing isn't for me.

Perhaps I should have just been born into the Hindu religion and my mother could have simply arranged a marriage for me.

After Antonio, my date, excuses himself and heads to the restrooms, a waitress makes her way over to my table. "Oh, my God," she gushes, staring at his ass. "He's a keeper. If you ever get bored of him..." she teases and trails off, sighing dreamily.

Somehow, I find the will power to not shove the model directly into the waitress' awaiting arms and steal his shiny sports car that's parked outside.

I pick at remains of my seafood dish. Antonio comes back and slides himself into the booth.

"Are you done?"

"Yes, all finished."

"Okay, me, too. Let's go." He smiles and asks a swooning waitress for the bill.

"Are you sure? You've barely touched your dinner!" I exclaim, feeling as though this conversation is usually the other way around.

My self-conscious companion nods and we exit the restaurant together after splitting the payment. We walk into the cool, already-dark night towards the metallic car that I swear has been the best part of this date. I decide that after becoming a full-fledged doctor, getting an expensive car will be one of the first things on my to-do list. Maybe I'll even get one for my mom so she'll be too distracted to nag about how she'll never have grand kids to spoil.

Before entering the Ferrari, Antonio surprisingly backs me up into a brick wall of a near-by building. He leans his right hand at the side of my face and bends down so I'm staring straight into his hazel eyes.

"I had a great night with you, Gabriella," he states, huskily, but all I can think about is how we should have received breath mints at the restaurant because the scent entering my nose is revolting.

Oh, wait.

Oh, no.

He's going to kiss me.

I never saw the face of the last man I kissed ever again.

Hm, maybe I should kiss him then...

Or not.

My knees bend at the last second, and I'm sliding down the rough wall while my date smashes his face against it.

"What the fuck?! What did you do that for?" he bellows.

"Sorry, sorry! I'm so, so sorry, Antonio." I stand back up to my full height. He's gripping his face in pain. "Are you okay?" I ask timidly.

"No! I'm not fucking okay. Why'd you move out of the way?" Dark red blood trickles from his flaring nostrils. I start feeling a bit nauseous at the sight of it.

"I didn't mean to. It just happened. I'm so sorry. Should we go back to the restaurant to get some ice for you?"

He wipes his bruising nose and winces. "Jesus. You broke my fucking nose."

Well, how was I supposed to know, and how'd he bash his face into the wall in the first place? Aren't you supposed to slowly lean in for a kiss and not rush into it like your face is a freight train? If I hadn't avoided him, we would've both been nursing injuries.

"You know what? This has been the worst date of my life. You've ruined my flawless face." He stumbles towards his car, wretching the door open.

"Are you going to leave me here?!" My voice rises an octave.

His parting words are, "Arrivederci, Gabriella," and he drives off, leaving me stunned.

I'm so going to kill Taylor for setting me up with this jerk. Or maybe she'll kill me for pissing off the umpteenth hot guy she's convinced to give me a chance.

I slide my hands into my pocket, looking around the barren parking lot. Great. How am I supposed to get home now? Both my hands are now searching my pockets thoroughly for any money for the bus fare. There's no coins, but I manage to find two five dollar bills so I'd end up having to over-pay the driver. Oh well, whatever gets me back to my safe and cozy apartment.

Right. So the bus stop is that way. Or the other way. I'm sure I'll find it sooner or later.

I scan my surroundings again, checking if there's anyone there. Feeling childish, I impulsively try to flip the bill to help me decide which direction I should take.

Abraham Lincoln is right. Lincoln Memorial is left.

The flimsy paper flutters to the ground. Right it is. As I'm bending down to pick it up, a huge gust of wind sweeps it out of my reach. Before I know it, I'm a frantic mess attempting to catch the escaping money. Several more gusts of wind follow until I can't even see it anymore, but I'm still running as fast as I can, maybe even hoping it'll spontaneously fall into my hands.

My foot hits something and I'm falling forward. The dusty ground seems to be coming towards my face at a mile a minute.

Thankfully, I get my hands in front of me just in time and I don't have to suffer the same fate as Antonio.

My head instinctively turns toward whatever or whoever caused me to trip.

It's a man and it's his outstretched leg that's gotten my whole life to flash in front of my eyes. I glare at him, then I get up and dust myself off. His face is mostly covered by his beard and his clothes are ripped and tattered. Even from where I'm standing I can still smell the odour coming from his scrawny body. It looks like someone could bottle up all the grease coating his hair if anyone would dare to. But he doesn't look too old, I notice. Maybe he's even close to my age.

The scruffy man grumbles, "Would you please spare some change, Miss?"

Okay, so he trips me, doesn't say sorry and then asks for my money?

I suddenly realize who he is. After all, every time the teacher would talk about something I already knew, I'd be doodling his name beside mine, with a heart between them, in the margins of my notebook. Memories of my old high school infatuation resurfaces. I won't let myself admit it to anyone, but under all the facial hair and grease, his good looks have only gotten better over time.

"Hi...er...Troy?" Should I have even spoken to him? I'm notorious for mistaking strangers for people I know. Just ask the man with dreadlocks at the airport who I met and thought was my aunt last year.

"Who are you? How do you know my name?" he demands.

"I'm Gabriella Montez. So are you Troy...Bolton?"

"Yes...how do you know me?" The man looks confused and somewhat scared.

"I went to your school, East High. Forgive me if I'm wrong, but I thought your face looked familiar. I mean, there were posters of you plastered everywhere since you were on the basketball team and was the captain everyone worshiped."

"Oh. You went to East High? I don't recall ever seeing you around. Were you the girl who had some weird crush on Chad and got her hair caught on fire when you guys were lab partners once in grade ten?"

"No... I just moved to Albuquerque halfway through my junior year. I guess you didn't see me because you were the popular jock and I was kind of a nerd, a Freaky Math Girl," I mumble the last part. But I have a sneaking suspicion that I know the identity of the sophomore he was talking about. So that's why Taylor was so strict about tying your hair up during science class.

He gives a defeated laugh. "Hey, don't be ashamed that you're smart. Look at me. I was the 'popular jock', and now I'm living on the streets, begging for money. And you were this so-called 'nerd' and you're..."

"A medical school graduate," I finish for him, but I mentally kick myself for rubbing his failure in his face afterwards.

"Nice. You know, I would've given up my popularity if it meant I wouldn't end up like this. To be honest, I could've focused on my studies more. Since my dad was the coach, he'd let me stay on the team even though my grades were slipping. And sometimes, my head wouldn't be totally in the game. I almost signed up for the winter musical during junior year and spent a good number of practices regretting that I didn't," he reminisces.

Surprised at how much he was opening up, I say, "So did I! I got pretty intimidated by those sparkly twins though. I showed up for the auditions and everything, but I chickened out and hid in the back."

"Ah, Sharpay and Ryan can be pretty scary. I planned to go to them too, but I had basketball practice and didn't get to it."

"That's a shame. I bet lots of our classmates would have paid good money to see the basketball playmaker in a leotard dancing to show tunes, doing spirit fingers."

"Somehow I have a feeling my team would've found someway to keep me from going anyways though."

"Troy...if you don't mind me asking, what happened? Before I left for the pre-med program, you led the East High Cougars or Lions—whatever—to winning the championships. And I heard you got a ton of offers from various universities. You, like, had your whole future planned out as a NBA star."

"Wildcats."

"Sorry?"

"We were the East High Wildcats."

"Oh. Well, I knew it was something feline."

"You were pretty close. I'll give you half marks for that." He smiles cheekily.

I pause, wondering if he's going to reply. "You don't have to answer my question. It was pretty personal, sorry."

"I predicted that you'd be curious." He shrugs but still doesn't answer my question or refuse to.

My right hand moves my left sleeve back, and I'm looking at my bare wrist. "Er, I really should go. It's getting late."

"An imaginary watch, eh? I used to wear those all the time," Troy jokes lamely.

"Very funny." I flush red. "Do you happen to know where the closest bus stop is?"

"That way." He points in the direction I came in. Left. Guess Abe was wrong.

"Thanks."

I start to walk away when a pale piece of paper hiding in a corner catches my eye. It's the five dollar bill from before, and it's been sitting here all this time, unmoving. I walk over and bend down to pick it up.

"Wow, wish I could randomly find money on the ground like that." Troy stares at me wide-eyed and looks at it longingly.

Feeling generous, I hand him the bill. "I lost this earlier and was chasing it. That's why I ran into you. You can have it, actually." I sternly advise him, "Spend it wisely."

"You bet I will. Thanks!" He grins widely and pockets the money. For his sake, I hope there aren't any holes it could fall out of. "And it's, uh, been nice talking to you, Gabriella."

"Likewise, Troy." I start to slowly leave, giving him a small smile over my shoulder. Every teenage girl would jump at the chance of talking to their high school crush. Ten years later, I got my conversation.