First Date with Derek

By: Dasey2020

Disclaimer: Life with Derek is not my own, all characters inspired.

*Hi everyone, thank you for the positive feedback on Dream Diary. I have now mapped up 4 chapters in total so I could explore their dynamic before going to University. This could be a prequel for future fics. Hope you enjoy, Let me know if you liked this chapter!*

Derek took in a deep breath as he waited for Emily to come outside. Everything with Casey had happened so quickly that he never ended up breaking up with Emily first. He felt guilty, Emily had truly been the first girl he built a good friendship with. Casey went into a fit of panic after they stopped kissing and questioned her morals. She had given him a slight slap and blamed him for being so charming and that she couldn't think. She told him nothing else could happen until he broke it off with Emily. She promised to break up with Truman immediately. They both agreed to keep their relationship a secret in the meantime. He smiled remembering her walking upstairs and yelling at him. "Don't you dare come close to me until your single. Got it?" She gave him that look, that determined look he had come to love so much.

"Hi Derek," Emily came out and gave him a hug. "You sounded pretty desperate to talk with me." She noticed the lack of his usual smile and immediately felt nervous.

Derek nodded and sighed. "Yeah, listen, I've been wanting to talk to you for some time."

Emily's face fell, she knew what those words meant. She had kept an extensive Derek journal all through high school and had studied his every move. He had been dating her for 20 days, she should have seen this coming.

"Go ahead," she managed to say.

"Look, Emily, I've been thinking about us for some time. Ever since graduation, actually." He stopped and felt so bad seeing her look dejected. "I am not good with the words, but you are going to Ottawa, and I'll be in Toronto. I just think you and I are going into different worlds, and-"

"We should break up," Emily finished. She looked at Derek and he nodded.

"I want you to know that I do care for you. I liked you a lot, but reality has changed for me. You deserve more than a half-assed relationship."

Emily smiled slowly. "I honestly had the same thought cross my mind, but I mean, I have dreamt of dating you since I was nine. I wanted to hold on to the fantasy of us making it work. I do understand, though. I want you to know you did live up to my expectations. I hope you and I can still be friends."

Derek smiled. "That is a relief, I was hoping the exact same thing. I hope I don't make your friendship with Casey weird."

She shook her head. "Casey will always be my keener bestie."

He laughed. They said a final good-bye and sauntered back to the house. His parents hadn't come back from their date. He went inside the house and up to Casey's room. She was on her bed reading a book. She glanced at him and slowly smiled.

"Well, I'm single," Derek said charmingly. "Casey McDonald, there's something I've been dying to ask you."

Casey got up and came towards him, a brilliant smile curving on her lips. "It's a good thing I am single too, then. Go ahead."

He gave her a slow-burn smile. "Will you be my girlfriend?"

Casey blushed and came closer to him. "I never thought I'd see the day, Derek Venturi." She put her hand on his chest and stared up at that face. She was worried this was all one dream still. "Yes, that's all I ever wanted." He reached for her and kissed her, setting fire to the beat of her heart.

Casey woke up the next day feeling blissful. She couldn't contain her excitement. Derek was her boyfriend. They had agreed to act the same around their family for the time being. It would be difficult to treat him the same after the scorching kisses he gave her the night before. She got up quietly. It was 7:00 am, no one else would be awake yet.

She put on some makeup, picking a blue eye-shadow color. It was the color she always wore to impress a guy. It seemed unreal that she was purposefully trying to impress Derek, though if she was truthful, she had always wanted his attention. She put on a pink top, and her favorite jeans. She beamed at the mirror.

She quietly made her way down the hall, trying to listen for any movement in the house. There was none. She felt flutters as she turned the doorknob on Derek's door. Derek never let anyone in his room without permission, and here she was giddy over being able to just walk in.

He was sleeping. Casey watched him for a moment, smiling at his disarrayed hair. He was still strikingly handsome. She lifted the covers and sank beside him. She spooned him, resting her chin on his shoulder, pressing herself into his back. He stirred quietly, opening his eyes.

He looked over his shoulder and grinned. "Thank goodness it's you, I was scared you were Edwin."

"You really can't tell the difference between this," she pressed in closer "and your smelly brother?"

He laughed and turned to face her. He put his arms around her and pulled her in. He kissed her nose, giving her small kisses all over her face. "So, let me tell you about this girl I scored with last night," he said in a husky voice.

Casey played along. "Derek! I don't want to hear about your little adventures."

He laughed. "Well, you have no choice, Case. I am going to tell you anyway." He rubbed her back slowly. "She's beautiful, smart, some would say she's a nerd, but that's never bothered me. She is hot-tempered, a klutz, and bossy as hell. She can't be put in a single category. She's cautious about everything, but also has a wild side occasionally. Have I mentioned she is a great kisser? A guy can't ask for anything better than that."

Casey blushed. "Who knew you were so romantic?" She suddenly felt jealous that a whole parade of girls had seen this side of him. She understood why they could never seem to resist him.

He scoffed. "I am not a romantic guy; please don't say that out loud it could destroy my reputation." He winked at her.

She gave him a cute pout. "Are you jealous, Case?"

"Extremely." She closed the gap and kissed his soft lips, he responded immediately. They kissed harder, and more urgently. They were too close.

He broke the kiss. "You're going to kill me. I really don't want anyone to find us like this, we should probably go downstairs."

She pouted again. "Fine, since when does Derek kick a girl out of his room?" He gave her an apologetic smile.

She got up and started to head towards the door. "Also, loving the eye-shadow."

Casey stopped, turned towards him, smiled shyly, and waved goodbye. She walked out of his room and sighed. Ugh, I am such a dork.

He shook his head. Casey had to be the most adorable creature that ever existed, and she was finally his. He got up and danced as he got ready, for once he didn't feel like being a jerk to everyone, he even wanted to hug his family, that's how happy she made him.

That night everyone sat down for dinner. Casey looked at Derek over the table, this would have to be the best performance of their life. They ate their meatloaf and listened to the rest of the family. Edwin was making jokes. Lizzie talked about her newest passion, marine animals. And Marty talked about her first crush. Suddenly Derek turned to Casey.

"You look like a raccoon," he said with that smirk. "Who's the poor guy that is going out with you now?"

Casey glared hotly at him. "None of your business, why don't you just leave me alone?"

He chewed his food and swallowed. "Does he know you're a nutcase?"

"Derek!" George sputtered.

"What dad? Am I saying something untrue?" He laughed.

"You're so immature, Derek!" Casey shouted. Her face going red. She noticed that twinkle in his eye. The plan was working, the family had no idea there was anything different.

The conversation changed to talking about a summer trip, and they listened in. Casey suddenly felt Derek's foot underneath the table, softly caressing her. She choked on her food. Was Derek playing footsie with her? She gave him a hard look, but he laughed and continued. She looked away from him and reciprocated. Why was this the sexiest thing ever?

After everyone had gone to sleep, Derek went to her room and they engaged in the hottest make-out session to date. Their "fighting" and the forbidden factor of their current relationship made the short time they had alone feel intense. He was on top of her, his hand was in her hair, and nothing else mattered. His mouth was teasing, assertive, and so playful. His other hand skimmed her hip, and he caressed her thigh. He pressed into her harder, and Casey thought she would die from embarrassment at the sounds that kept coming out of her mouth. He was inciting dangerous feelings, and she pulled back, breathing hard. He seemed to understand, but the sizzling way he looked at her made her crazy.

A whole week passed, and they carried on their typical rival relationship in front of the world. Any moment they had alone was spent kissing, cuddling, and talking. But the talking was minimal. Eventually, Casey just wanted more.

"Der," she said to him one night as he kissed her neck. "I want to go on a date with you."

He stopped and looked at her with confusion. "How exactly could we do that? There's no way we could go anywhere safe enough where we could just have a date."

Casey mumbled. "I am your girlfriend, but it doesn't seem like I am. I have loved the kissing and the cuddling, but you know me. I need to build a strong emotional connection as well. I love to talk, I want romance, surely you must know that about me."

Derek laughed. "Of course, I know that. I find it so cute."

She pulled back. "I don't want it to be cute, I want it to be something you want as well. I want you to want to date me." She stammered for a moment. "I saw you take girls on dates for the last three years, they all raved about what a great date you would give them. I deserve romance, no not just deserve, I demand it."

Derek just stared at her, understanding he had messed up already. "I uh, have never been a super romantic guy. A lot of the time I just said what I thought the other person wanted to hear. I am worried you will get sick of my inability to express my thought or emotions."

She softened and gave his cheek a pinch. "I know who you are Derek, and I don't want to change you, ever. I am just so jealous-"

He cut her off. "There's nothing to be jealous of Casey. I have never felt for anyone the way I feel for you."

"Not even Sally?" Her voice quivered.

Derek reached for her hand. "Sally was important, I won't lie. But the way I feel about you has always been exponentially greater."

Casey raised an eye in surprise. "You used the word exponentially, what's wrong with you?"

Derek shrugged, a coy smiled covering his lips. "I don't know, it just came to me. You make me smarter."

Casey melted. "You're the cutest, Der." She kissed his cheek.

Derek couldn't deny her anything. "About that date, what if we told our parents we were invited to a party out of town in Toronto and we also wanted to take the opportunity to go see the campus?"

A flicker of joy went over Casey's eyes. "Really?"

He smiled at her. "Just promise me you won't have your expectations too high. I know how much you like things to be perfect, and I will try but please, don't dump me if I fail."

Casey had never felt more love for Derek than she did right then. He could take her to a garbage dump and still, she would find him the most charming guy on the entire earth. It was just Derek she wanted. It always had been.

"I could never dump you, silly. It sounds perfect." She grinned and kissed him goodnight.

That weekend they made the plan to leave early. George and Nora thought it was a good idea to see the campus and were surprised that Derek was interested in checking out the university. They were given a curfew for the party and needed to be back no later than 1:00 am.

Casey was so excited, she put on a normal outfit, and in a separate bag, she put in her date outfit. Derek told her to dress up for the occasion. When she went outside, George was talking to Derek.

Derek feigned annoyance when he saw her. "Pray for me dad, I will have to deal with being in a car with Casey and her girlish music."

George smiled and gave them a quick hug goodbye and left them.

Casey and Derek stared at each other for a moment. "So, this is really happening," Casey mused. He nodded, but he was feeling nervous. He had dreamt of dating Casey for such a long time, the pressure was getting to him.

She then pulled out her bag. "It wouldn't be a Casey and Derek adventure without," she said mysteriously, "crustless cucumber sandwiches! Just don't throw it out this time."

Derek laughed. "You forgot to climb down the tree. What happened to the daredevil I know?" She gave him a dashing smile and giggled.

They drove in silence for some time, listening to music. Derek held her hand the entire time. Casey looked out the window and couldn't help but smile. "So, what's the plan?"

Derek pursed his lips. "Nice try, Space-Case, this is a surprise remember."

She whined. "You know surprises stress me out, please give me a hint."

"Alright, we are going to do something I have mocked before." He smiled broadly at her.

She scoffed. "You literally mock everything, that doesn't help me."

He smirked. "It's something you're really good at. I know it'll be hard to figure that one out, since apparently, you're good at everything. Could you be more perfect?"

Casey blushed. "Okay, I'll let you surprise me."

The first part of Derek's date was what he called the "entry" date. He took her to a lake, and they walked around, holding hands. It felt so strange to be able to hold hands without looking over their shoulders. He led her to a beach. They flirted with one another and watched the sun peak over the water.

Derek pulled her into an embrace and kissed the top of her head. "I love you," he murmured.

She looked up at him and beamed at him. "And I love you. This is simplistic but so romantic. I love the beach."

They sat for some time, Casey rested her head on his shoulder. She had never been more at peace; she would have never imagined getting to see this side of Derek. She did miss his evil schemes, though. She suddenly got up and quickly grabbed some water and splashed him.

He laughed. "Oh, you are dead now." He got up and chased her around the beach, her laughter echoing. He reached for her waist and pulled her towards him. He kissed her, but then he suddenly lifted her. "It's a good thing you brought extra clothes," and with a twinkle in his eye, he threw her off the dock. Casey came up from the water.

"Derek!" She sputtered. "That's no way to treat your girlfriend!" She said seriously, but then laughed as she saw his smile leave his face instantly. "I'm just messing with you, who knew you were so sensitive?"

He chuckled, and then jumped in. They were both swimming around each other, both trying to splash the other. Derek swam closer to her, he put his hands underneath her and threw her up, and away from him, creating a huge splash. Casey swam towards him, her eyes sparkling with excitement.

"Coming for more, Casey? You really think you can take me on?" He loved provoking her, and she knew it. She grabbed his arm and pulled him in towards her, and she kissed him, taking the moment of distraction as a moment to dunk him under. After some time of the splash fighting, he helped her out. He rubbed Casey's arms as he noticed she was shivering.

"Alright, next you need to go clean yourself up. We are going to," he drummed on his lap dramatically. "The theatre." He used an announcer's voice.

Casey looked at him, shocked. "You are taking me to the theater?"

"Yes, there is apparently a phenomenal Broadway production for Moulin Rouge." He gave her a hopeful smile. "I know how much you love that movie. And you mentioned you played the lead in a musical before."

Casey was speechless. "You hate musicals though, you told me it was the definition of boredom."

"If I get bored, I'll just look at you." He flicked water droplets at her and laughed as she feigned annoyance. "Just so you know, you changed my mind about musicals. That's why I played the pirate, I just wanted to be near you, and I admit, it was sort of fun. Just don't tell the guys, please."

"I don't know what to say," she whispered. "You really do know me." She looked in his eyes dreamily.

"Just years of observation, that's all. I have the upper hand, I got to live under the same roof as you. I'm sure not many other guys had that advantage," he grinned.

Derek led her to the change room, and when she came out, he was stunned. She wore a red velvet dress that cut off at her knees. She changed into high heels and did her makeup. Her hair tumbled down in slight waves.

Casey looked down shyly, as his eyes trailed down her body, and up. "You are a babe," he muttered. He had changed into a sports jacket, and he looked so handsome.

"You aren't too shabby yourself," she breathed.

He reached out for her hand and they went on their way. They went to the theater and Derek was fascinated by Casey's reaction to everything. The music would play, the characters would talk, and Casey's eyes were locked on that stage completely in awe. He loved seeing the pure and adorable joy cross over her features. He held her hand and watched her continuously. Casey was his girlfriend. The show ended and she leaped across the chair and hugged him.

"Thank you, Derek, this has been the best date of my life." Never would she have imagined this, and it was a sense of pride that this date had been tailored to her. She knew it wasn't a duplicate. He rubbed her back and laughed.

"You are welcome, but the night is not over." She leaned back and stared at him.

"Derek, you already did enough. This must have cost you a fortune. I hope you are not doing this because you think I want an elaborate night."

He shook his head, and sweetly smiled at her. "Nope, that's not why. I told myself a long time ago if I ever got a chance to date you, I would make it memorable. I also got jealous of all the guys you dated. I need to upstage them, remember what Derek wants, Derek gets." He winked.

She couldn't help but break out in a smile. She followed him out of the theatre, and a thought crossed her mind. Three years. She had wanted him for three years, and now she didn't know why she denied her feelings in the first place. She couldn't help but mourn the time lost.

Derek took her to a restaurant; it was more lavish than Smelly Nelly's that was for sure. Derek sat across from her, and they stared at each other.

"Now, there's a reason I picked this restaurant." His eyes looked mischievous. "They have the best Duck Orange. I always felt bad you missed your surprise party."

Just when she thought Derek couldn't surprise her more, he did. Her face pinkened. "Derek Venturi, where have you been all my life?" She stammered.

"I've always been here, Case."

The rest of the night went on like a dream. They talked for hours, reminiscing about all the pranks he played on her before. All the times they wanted more, but were too scared to make a move. He also picked that restaurant for the live music and had pulled her to her feet, and they danced together. The music was slow and jazzy, and they clung on to each other, completely suffused. She buried her face in his neck as he led her gently. Her face was burning from the intimacy, it wasn't just the physical closeness, it was the terrifying feeling that there was no going back now. If this were to end badly, it would ruin her for the rest of her life. Derek had secretly observed her for years, taking mental notes of the things she would want, and he was just doing them. It didn't seem like this was Derek Venturi at all, or maybe the Derek she had known before was just an elaborate cover-up. By the time they got back home, Casey was starstruck. They tried to walk in with their usual angry banter, but Derek just slung his arm around her shoulder.

Nora and George sat on the couch and turned to see them. Casey was smiling, and Derek had his arm around her. They had noticed ever since Truman kissed Victoria that Derek had been more protective of her. It was a breath of fresh air for them.

"Did you have a fun night you guys?" They asked with curiosity.

They both nodded, not responding.

"Wow, did you two work out your differences or something?" Nora asked happily.

Derek looked at Casey, smiled, and turned back to them. "I guess you can say there's a new understanding between us."

Nora squealed, and George let out a hoot. "I thought I'd never see the day, you two look like real siblings now."

Casey looked at Derek, his molten eyes were bright, and he looked at her with the kind of passion she always longed for. They didn't even flinch at the word "sibling." She giggled. "Trust me, we will never be the same."

They walked up the stairs, leaving their parents with their mouths open. Derek walked Casey to her room. He rested his forehead against hers and let out a breath. "I'm sorry, I couldn't let go of you."

She cupped his face. "I don't want you to let me go, ever."

He kissed her sweetly. "Goodnight, Princess."

Author's note: What did you think about this date? Let me know :)