A/N: Happy Birthday LexiTheAmatuer! I took your love of all things Georgetown-era and wrote this for you. I hope you like it!

PS – Because there is a handful more in my brain, this can easily turn into a collection of 'firsts'. It's up to the birthday girl and all of you lovely readers if it happens.

White? She shakes her head. Too innocent. She adds the top to the growing pile on her bed. Red? She tilts her head to the right, considering it before deciding against it. Too sexy. The dress flies across the room and lands on the foot of her bed. Black? Her eyes widen. Neckline is way too low. Pink? She rolls her eyes. No way. Jeans? Skirt? Dress? One by one, articles of clothing fly from where she stands in her closet and land on or around her bed.

"Ow!"

She turned to see Owen standing at the entrance to her closet with two glasses of wine in his hand and her purple sweater on his head. Giggling, she rushed over and grabbed her sweater.

"I'm sorry." She said, accepting the glass he offered.

"Those buttons hurt, sis." He complained, rubbing his forehead. "What the hell are you doing?" he asked as he looked around at the mess of her usually immaculate bedroom.

Sighing, she walked over to her bed and sat on the edge. "I'm trying to find something to wear." Placing her glass on her nightstand, she rummaged through the clothes next to her. "I just can't seem to find the right thing." She whined.

Taking in his sister's anxiety for the first time since entering her room, he realized what this was about and gasped. "Oh my God! Tonight is the night, isn't it? The big first date with Mr. Georgetown?" She nodded. "Well, why didn't you call me for help? You can't do this on your own!" She glared at him in response. Placing his glass next to hers, he grabs the first thing he sees. "This. Wear this. With your 'fuck me' heels. The black stiletto ones." He says as he holds up her red dress.

"Owen! No! I can't wear that. Not with Will." She shook her head. "This is weird enough. Going out on a date with my best friend. I don't want to look like one of the sluts he usually goes out with."

"I've seen the way he looks at you. You have nothing to worry about. Trust me." Knowing his sister well enough, he changed his approach. "Where are you going? Do you know?"

"To the movies." She shrugged. "Maybe for a drink after? I don't know."

He nodded his head, decidedly. "Casual, it is." He started to go through the pile, shook his head and went back to her closet. Emerging with a pair of deep blue jeans, he tossed them to her as he made his way back to the pile. "Wear those. Your ass looks perfect in them." Finding what he searched for, he tossed the black top to her. "And wear the boots mom sent you." He put up his hand to stop her protest. "Alicia, please. Will you trust me? The outfit is simple, but sexy. Now get dressed so we can do your hair and makeup. Go." He says as he gently pushes her toward her bathroom.

An hour later, a nervous Will is making his way up to her apartment. His heart is racing and he slows his pace hoping to regain his composure before reaching her door. What the hell is wrong with you, man? It's Alicia. Your best friend. In reality, he knew that was precisely why he was so ridiculously nervous. He couldn't explain it, but she was special. Not like all of the other girls he's dated. It was important to him that she understood that. Reaching her door, he took a deep breath before knocking. Glancing at the bouquet of vibrantly colored frangipani in his right hand, he prided himself for having the local florist order them because he knew they were her favorite.

The door opened and his breath caught. He'd grown accustomed to seeing her in sweats or clothes that hung loosely from her body. Here she was, standing before him in jeans that hugged her curves, a blouse that showed more of her porcelain skin than he'd ever seen before and boots that made her beautiful legs look longer. She invited him in. Realizing that he still hadn't greeted her, he finally made eye contact and smiled. "Hey." He breathed. She smiled and he could swear his heart stopped beating for multiple seconds. Blinking, he remembered the flowers in his hand. "These are for you." He held the bouquet out to her.

"Frangipani! Will, these are my favorite. How'd you know?" She replied as she closed the door behind him.

"I think I remembered you mention it once." He looked away, shyly. Get it together, you fool.

"You remembered that?" she glanced at him, curiously and he nodded, shrugging slightly. "Well, they're beautiful. Thank you." She smiled back at him. What is it about that smile that makes my heart stop and send chills down my spine?

"Here sis, let me grab those and put them in water." Owen said as he took the bouquet from her. "You two should get going."

"Yeah, movie starts soon, I know how you hate to be late for anything."

Chuckling, she reached for her purse which sat on the arm of her sofa before moving toward the door.

"You two have fun tonight." He turned his attention to Will. "Please do bring her home late. Or not at all. Whatever floats your boat." Alicia whipped around and glared at him, making Will laugh. "I love you." He said, placing a tentative kiss on her cheek. "Have fun." He repeated.

By the time they emerged from the movie theater hours later, any lingering nerves or awkward feelings were laid to rest when he tentatively grabbed her hand as they walked and she entwined their fingers in response. They walked for awhile, without any destination in mind, talking about any topic that came to either of their minds and sharing stories from their lives that had both of them in fits of laughter.

"I can laugh about it now, but I had no idea what to do with him in that moment." She said between giggles. "He was high and wouldn't shut up and my mom was drunk but my dad knew something was going on."

He laughed and looked around at the shops around them. "Hey, are you hungry? We could grab a bite to eat if you want."

Scrunching up her nose, she shook her head slightly. "Not really. Are you?"

They both glanced over at the family that passed them and eyed the children happily devouring their ice cream. Making eye contact, they both smiled. "Ice cream!" they said, in unison.

Placing his hand on the small of her back, he guided her out of the unusually busy for a late October night ice cream parlor and grabbed her hand in his again once outside. It was hard for him to ignore the feeling of electricity shooting through him whenever he touched her and he wondered if she felt it, too.

They walked in silence for a few minutes, the noise of the shop slipping farther away with every click of her heel meeting the concrete of the sidewalk. He thought he felt her shiver and glanced over at her. She looked up and smiled shyly. "Are you cold?" he asked her. She shook her head. He nodded and turned back to his cone. Feeling her tremble again, he stops walking and turns to her. "You're cold. Don't deny it. You didn't bring a sweater and you're eating ice cream."

"I'm fine, really." She insisted.

"Hold this." He handed her his cone and started to take his jacket off.

"Will, no, don't do that. It's not necessary." She tried to stop him, to no avail because he didn't listen.

He helped her into his jacket. "There. That's much better."

Smiling sweetly, she handed him his cone. "Thank you." She watched as he licked the ice cream. He looked at her, questioning her with his eyes. Taking a step forward, she closed the space between them. Glancing at him nervously, she raises herself on her toes and kisses him softly for the first time. Pulling away, she smiles when she sees that his eyes are closed. Opening them, he returns her smile. "I was jealous of your ice cream." She tried to explain her act of spontaneity.

"Is that so?" she nodded, smiling flirtatiously. "Well, in that case…" He grabbed what remained of her cone and tossed it into the nearest trash can with his. Rushing back, he pulled her to him. She laughed and shook her head. He took in how beautiful she looked in that moment; raven curls bouncing with the shake of her head; green eyes sparkling with delight. She took his breath away. "You have a good laugh." He said before leaning down to place his lips on hers. Reaching up, she placed her arms around his neck and ran her hand through his hair lightly, deepening their kiss. She pulled away slightly when she felt him tremble.

"Now you're cold."

He looked into her eyes and smirked. "That's not because I'm cold."

"Neither was I." she admitted to him, confirming that she, too, felt the electricity when they touched.

He placed his lips on hers again and she smiled into the kiss as he wrapped his arms around her tighter and slightly lifted her from the ground.