A/N: Guys I am not fashionable... Most of my outfits on a day to day consist of baggy sweats, tshirts, and flip flops. I show up to school in pajamas sometimes. (Sometimes I don't even wear deodorant but that's a story for another day ahahaha). So if Riley's outfit seems wack, blame my ignorance in all things fashion and looking cute.

Thank you for the reviews everyone! You all are so sweet! :)

Disclaimer: I do not own GMW (and it's a good thing too haha because I am crack shipper trash...)

"Alright mom and dad! I'm going to bed! Goodnight!"

Riley had her head out of her bedroom door, her hands cupped around her mouth.

"Goodnight, sweetie!" Topanga called back from the living room.

Sighing, Riley closed her door and cut her main lights off, turning on the lamp beside her bed in order to see. It was just about a half hour til, so she had a little bit of time before she had to get to Bleecker Street. She couldn't believe she was really about to sneak out just to go on a date with The Rebel. A date she knew she was terrified of, but still, a date nonetheless.

She dialed her first speed dial number and waited as the call rang, nervously twiddling her thumbs.

"C'mon Maya… Please pick up the phone…"

And then the call went through, and she could hear Katy's laughter in the background.

"Alright Riley. Open up your closet." Maya said, cutting to the chase.

"Right."

Riley opened it up and peered inside at the meticulously folded jeans and neatly aligned shoes and shirts and sweaters and vests hung by colour coordination and by length of sleeve. She turned and faced her bed, where she had already thrown out tons of clothes from her open dressers in halfhearted attempts to put a good ensemble together. She didn't even know where to begin.

"Maaaayaaaa…" Riley whimpered, slumping on her bed. "I don't know what to pick."

"Riley? You're going to be okay." Maya sounded slightly exasperated on the phone. "So here's what we're going to do. I'm going to explain something to you, okay? You ready?"

"Yes. Explain away."

"Now this is a first date. So what you wear will determine what the guy will perceive what you perceive the date as. You dress to kill either way, right? But how you dress to kill will determine the outcome at the end of the night."

It sounded like Maya was speaking a whole other language entirely, and Riley frowned, letting out a slow breath.

"I-I don't understand."

"Let's put it this way: if you show too much cleavage, he'll probably think you're trying to go for the hook up on the first date thing. And you don't want that."

"Right. I don't."

"You want to dress to impress, but you need to stay true to yourself." She said, "Where is he taking you?"

"He didn't say…" Riley said, chewing her lip in worry, "Is that going to be a huge problem?"

"Nope. We're still fine."

"So what do I wear?"

"We're gonna go for cute with a little bit of sass." Riley could hear the volume of a game in the background decreasing as Maya walked away from the source of the noise. "Crop top. High waisted jeans. Trust me. It works for any late night date. And it'll work for a date with The Rebel."

"Okay. I like the sound of that." Riley said, grinning goofily.

"Good. And I know exactly what would work. You know that black floral crop top you never gave back to me?"

"What?" Riley scoffed, "I definitely gave it back–"

"It's in your left top drawer on top of your bras."

Riley's eyes widened in surprise as she checked inside the aforementioned drawer and found the shirt innocuously resting inside.

"…How do you do that?" Riley muttered under her breath.

"Wear that shirt. Match it with those faded high-waisted jeans of yours. The ones with that one tear on the knee."

"But there's a tear on the knee!" Riley said emphatically, "I can't wear that out in public."

"Exactly."

"Ooooooh…" Riley said, "I get it."

"You still got those tan ankle boots in your closet?"

Riley rummaged around on the floor, searching for them towards the back. She found them behind her box of china dolls she used to collect.

"Yes, they're still here."

"Great. Now put it on. You've got fifteen minutes."

Riley obliged, yanking off her night dress and putting on the clothes for the date, her trepidation growing with each passing second. She was seriously about to sneak out to go on a date. With The Rebel no less!

"Riley, I can hear your thoughts all the way through the phone. You need to relax okay? He's going to know you're super stiff and uncomfortable."

"But I am uncomfortable!" she hissed through the phone in the way that people did when they were trying to be heard, but speak softly, "I'm about to go on a date with The Rebel of all people. I mean he's the Rebel Maya. The Rebel! And I'm the exact opposite of a rebel! I don't get it at all! Why would he want to date me?"

"Because you're cute and you're sunny and you're quirky and you're funny Riley. You make the lives of everyone who meets you better. Why wouldn't anyone want to go out with you?"

"Because I'm weird and I go off on tangents and I ramble and I'm clumsy?"

"You know those are actually pretty endearing traits on you."

Riley sighed, smiling, "I'm sorry… I'm just freaking out over here…"

"I know you are. That's what I'm here for. To help you get that freak-out out of the way so you can enjoy this date."

Riley checked herself in the full length mirror attached to her closet door, turning to and fro and making sure she looked ready.

"I feel weird… What am I supposed to say or do?"

"That? I can't help you with. But that's the easiest part. You just have to be you."

"Thank you Maya… I don't know how I could do this without you."

"You don't have to. I'm just a call away, okay? If you need advice or someone to come kick his ass, I'll be right there."

"Okay, checklist time." Riley said, walking over to her window bay and picking up her wallet.

"Got your ID?"

"Check."

"Some cash for a taxi if you need it?"

"Check."

"Metro card?"

"Check."

"Keys in case you can't go back through your room?"

"Check."

"Cellphone?"

Riley looked around frantically when she realized she couldn't see it anywhere.

"Wait… where's my cellphone? Maya I think I lost my cellphone!"

"In your hand Riley…" Maya sighed.

"In my hand… Right…" Riley chuckled nervously, tucking a strand of hair behind her ear, "Check."

"Okay. Riley Number Two."

"Got it."

Riley gathered her clothes off of her covers and arranged them underneath the comforter in a lopsided formation, like Maya had taught her all those years ago. She made sure it looked like an actual human body and not a lumpy sack of potatoes, and when she was satisfied with her work, she smiled triumphantly with her hands on her hips.

"Check."

"Alright. Lights off. And window check."

Riley turned off her lamp light and then cut the light off in her closet, throwing her room into semi-darkness, illuminated only by the stars and moon in the night sky. She walked over to her window and pried it open, poking her head out and looking outside to make sure none of her neighbours were enjoying the cool night air and having a smoke on the escape. If they saw her, they would tell her dad and then she would be cooked and fried like an egg and then served on a whole wheat English muffin with Hollandaise.

"All clear?"

"Check."

"You have eight minutes to get there. You think you'll be okay?"

"I-I think so. It's just a date. It's not like I have to marry the guy…" And then Riley gasped dramatically, "I don't have to marry him do I?!"

"Now you're just being ridiculous, Riles."

"You're right… Okay. I'm heading out now. I'm ready."

"Alrighty then. This is where I leave you. Good luck, pumpkin." Maya said softly, "Now if you'll excuse me, I need to go beat my mom at Just Dance for once in my life…"

Maya hung up and Riley tried not to think about how alone and scared she felt without Maya's constant voice in her ear telling her what to do. She wished she could just take Maya on the date with her, but she knew she had to do this herself. She had wanted a street sign. So now she had to reap the consequences of what she sowed.

So taking a deep breath and preparing herself, she climbed out of her window into the warm night air and crept down the fire escape to the sidewalk below. She walked through the streets, head held high amongst the bustling crowds of people, hoping they couldn't see the 'curfew breaker' sign sticking out of her head. But no one paid attention to the lone teen girl, all too busy with their own endeavors to be wondering why she was walking out on the street in the middle of night. Each step she took to her destination was less anxious than the last, and Riley felt herself relax somewhat. After all, she'd survived sneaking out of her home, how bad could this be?

She approached the corner of Bleecker Street, and saw The Rebel waiting for her, nonchalantly leaning against a streetlamp, chewing on a toothpick in his mouth.

"Now or never Riley…" she murmured encouragingly to herself.

She took a deep breath and then walked straight towards him, trying to keep her steps steady so she wouldn't have a tumble and land on her face.

"So where are we going?" she asked, once she was in front of him.

He smirked, taking the toothpick out and tossing it in a nearby bin.

"You'll see."

She chewed on her lower lip in worry.

"Okay… but I really shouldn't be out this late especially since I have a test tomorrow. And I don't think there are very many places that will be open for long so if you were planning on taking me to the movies or something, I think you should have picked an earlier time."

"I'll have you home by one, Matthews."

"Can I at least have a hint of where we're headed to?"

"Do you trust me?"

Riley was a little taken aback by his sudden question, and she held his stoic gaze, silently searching his eyes. She should have honestly been apprehensive or maybe uneasy, but she didn't feel that way at all. There was something about him that made her realize she actually did trust him, as weird as it sounded. She barely knew the guy, and quite frankly, it wasn't a good idea for her to put her trust in someone who obviously had no qualms stealing city property, but she did.

"I trusted you to get the street sign for me by Friday. And you did." She replied honestly, "So I'll trust you again."

His silent regard of her subtly changed, and she could see the pleased smile in his eyes, even though his expression remained the same. Her cheeks flushed a little, and she averted her gaze, staring at her taupe boots shyly.

"Alright then." He said, turning around and walking further down the street. "Follow me."

Riley nodded and followed behind him, hoping so badly that she had made the right decision and that she wasn't about to walk into something absolutely crazy.