Hey there guys. Thanks for the all the kind reviews, it really motivates me to write more of this story. I stole some lines from the show because I suck at date dialogue, so please don't sue me NBC.

I finished this chapter a couple days earlier then I thought I would, so i'm uploading it a little early. Hopefully the rest of the story comes to me as easily.

This is self-beta'd so I apologize for any mistakes that may exist. Once again, hope you guys enjoy, all reviews are appreciated.

I don't own anything, especially not Chuck.

Chuck vs The Rich Girl

Chapter 2: Many Firsts and the First of Many

Saturday August 13th

Chuck was excited for his date tonight with Sarah. He didn't often go out on dates with the likes of Sarah Walker. To be honest he didn't go on dates very often anymore, so while he was excited, he was also extremely nervous. He had decided to do something simple for the date; dinner and dancing. He hoped that Sarah would appreciate doing something low-key because she didn't seem to like to flaunt her wealth. He was still worried; worried that he was wrong, and that what he had to offer wouldn't be enough for her.

His thoughts and anxieties were interrupted by the ringing of his cell phone. He glanced at the caller id and saw that it was Ellie. He answered right away.

"Hi Ellie"

"Hey Chuck. You free for dinner tonight?"

"Sorry, no can do." Chuck said, preparing himself. "I've got a date tonight." The squeal that came from Ellie was so obnoxiously loud that it almost caused Chuck to drop his phone.

"Oh my god! Who is she? Where are you taking her? What are you going to wear?"

Chuck was overwhelmed by the barrage of questions fired from Ellie. "Well, her name is Sarah and she is incredible. I'm thinking about taking her out for dinner and dancing, and I'm not sure what i'm going to wear." Chuck answered honestly.

"I'm coming over i'll be there in 10." Ellie said, quickly hanging up the phone.

Chuck gulped. "Wait what? Hello?" He laughed when he realized Ellie had hung up on him. Sure enough, 10 minutes later, Chuck heard a knock on his door. He opened the door for Ellie, and she just brushed past him, walking to Chuck's bedroom.

"It's time to get you ready for this date." Ellie announced.

"Thanks for the help sis but it's really not necis…."

"You really think i'm not gonna help you get ready for your first real date since Stanford? Don't be ridiculous." Ellie interjected while searching through his closet.

"Here, try this on." She demanded, holding out a dark blue button down shirt. Chuck sighed, but put on the shirt.

"You look good. That and a pair of nice jeans will be perfect." Ellie noted. "Trust me Chuck, i'm a girl. I know what girls like."

"Thanks for the help sis."

"So this Sarah, what's she like?"

Chuck paused for a second. "She's... she's perfect." He finally said, his face lighting up with a huge smile. "She's smart, and funny without trying to be, and beautiful..."

Ellie was really happy that Chuck was going on a date, but seeing the look on his face when talking about Sarah made her heart soar. All Ellie wanted was for Chuck to be happy, and while he had a good job and friends, he was missing something. So when Chuck was describing Sarah to her with a look of happiness on his face, all Ellie could do was smile.

"I'm really happy for you Chuck. She sounds amazing." Ellie admitted.

"Yeah she is." Chuck agreed, then paused with a fearful look on his face that Ellie caught.

"What's wrong?"

"I'm just afraid of screwing it up, that's all. She's kinda out of my league."

Anger flashed across Ellie's face. "Don't you say that!" She snapped, frustrated by Chuck's continuous self-esteem issues. "You are amazing and any girl would be extremely lucky to have you. You aren't out of anybody's league." Ellie really hated when Chuck put himself down like that. His confidence has been at an all time low since Stanford, and she was frustrated that he didn't see himself in the same light as she does.

"Just be yourself Chuck. That's all it takes." Ellie said softly.

Chuck grinned at Ellie's pep talk. "Thanks sis."

He knew that she was right. There was no chance for this to work if he tried to act differently because he was nervous. He had to be himself, and hope that she liked him. Frankly it was hard for him to imagine being good enough for Sarah, but she already said that she was going to ask him out if he didn't, so maybe it wasn't that much of a stretch. Ellie's words helped, like they always did, but ultimately it was on him. He wasn't gonna get a girl like Sarah while wallowing in self-pity. He needed motivation to get over the events of Stanford, and Sarah was the perfect catalyst.

He would do everything in his power to make tonight perfect. He was going to take Sarah to Antonio's, an Italian restaurant that was highly recommended by Morgan. Morgan may be considered a screw-up to a lot of people, but one thing he was good at was picking restaurants. Truly he had a gift. After dinner he was gonna take her to a dance club that was a couple blocks away. He hoped she would like this simple, low-key evening, because that's all he could give. He wasn't rich like some of her ex's probably were, so he couldn't do some extravagant over the top first date. This was all he could give, and hopefully she would appreciate that. If not, there was nothing he could do about it.

Sarah was putting the finishing touches on her makeup when she heard a knock on her door. She glanced at the clock and saw it was exactly 7:00 pm. Just like Chuck to be exactly on time she chuckled to herself. She walked over and opened the door for him, and smiled.

"Hi Chuck."

Chuck was floored. Sarah was wearing a leopard print blouse with tight black pants and a black jacket. She looked breathtaking.

"Wow… you look amazing." Chuck said, finally snapping out of the trance she put him in.

"Thank you. You look good too." She responded with a shy smile. Every time Chuck complimented her it made her heart flutter. Nobody's words has ever had that effect on her before. "You ready to go?"

They walked together down to Chuck's car in complete silence. Both were extremely nervous, and it was shown by the lack of conversation. Once they got into the car however, the story changed. Conversation flowed freely. They talked about their hobbies and interests, and Chuck was shocked to find that Sarah didn't have a favorite band, which was something that he planned on fixing. The nerves they were both feeling instantly evaporated, and they just enjoyed each other's company.

Sarah was ecstatic when Chuck announced the plans for the evening; dinner and dancing. She liked simple, especially because everybody tried so hard to impress her when they found out who she was. It was exhausting. She wasn't attracted to the extravagance that came with her wealth. The night that Chuck had planned for them was perfect.

At Antonio's, the conversation continued to flow. Almost everything Chuck said put a smile on Sarah's face.

"You're a funny guy. Which is good, cause i'm not funny at all." She acknowledged.

"Is that your secret? Cause I was sitting here wondering what's wrong with you, and it was either you're a cannibal, or you aren't that funny, and I was rooting for cannibal because I've never met one before."

"Nope, not a cannibal. Besides, you already know my secret. Well that, and the fact that I just came out of a long relationship, so I may come with some baggage."

"Well I could be your own baggage handler." Chuck blurted without thinking. He immediately put a grimacing smile on his face, extremely embarrassed by the corny thing that came out of his mouth.

Sarah on the other hand thought it was extremely cute. It wasn't a line, it was entirely honest. Whatever issues she had, she knew that he would help her with them, not judge her for them. When she saw the embarrassment in Chuck's eyes, she decided to try to make him feel better. So she flashed her biggest smile and said "I like you Chuck."

The look in his eyes said it all. The embarrassment was replaced by genuine happiness. If this was gonna happen every time she said that she liked him, she would say it a thousand times over. The look made her heart stop. Nothing Bryce ever did, or any of her past boyfriends for that matter, ever made her feel this way. For whatever reason, Chuck Bartowski made Sarah Walker feel things she had never felt before.

By the end of dinner, both knew there would be at least a second date, if not more. They just connected on a deeper level. Neither knew a better way of explaining it. When it came time to pay, Sarah reached for the check, but Chuck refused to let her pay.

"I'm the one who asked you out therefore i'm the one who pays." He reasoned.

"Don't be ridiculous. Let me pay, I have plenty of money."

"I don't care." He said bluntly. "How about this, if you ask me out for a second date, i'll let you pay for that one." He winked at her.

"OK. Wanna go out again sometime?" She asked, laughing at the absurdity of the situation. She did respect that Chuck was trying to show that he didn't care about her money, but it was completely unnecessary.

"Hmm…." Chuck pretended to think about it, as if the answer wasn't obvious. Finally, he said "I'd love to."

They went straight from the restaurant to the dance club. They both felt a connection earlier when they talked, but that connection was even more obvious when they danced together. Sarah loved to dance, but she didn't expect Chuck to be such a good dancer, with his lanky frame and clumsy nuances. When they danced together, it was almost like they became one.

"How did you become such a good dancer?" Sarah asked, genuinely curious.

"When I was in high school my sister Ellie forced me to get dancing lessons. She said it would help me get girls."

"She was right. Girls find good dancers hot." Sarah said, winking at him. Chuck gulped and chuckled nervously. Chuck was now extremely thankful that Ellie made him get those lessons.

Eventually the date was over, and they ended up in front of Sarah's apartment complex. She was considering asking him upstairs, but decided against it. She knew he wasn't the type to do that after the first date, and truthfully she usually wasn't either, but with Chuck she would almost do anything.

"I had a lot of fun tonight." She said.

"Me too." Chuck agreed. He leaned in for a goodnight kiss, which Sarah immediately reciprocated, glad that he got the hint. The kiss was soft and tender, and the spark was unlike anything either had experienced before. They both let go of the kiss, locked eyes, and could tell that the other was thinking the exact same thing.

"See you Monday at work." Chuck said and turned around.

Sarah entered her apartment complex, while Chuck walked back to his car. Best first date ever. They both thought. Sarah had never been on a date with such a gentlemen before, and a funny one at that. Almost everything he did was to please her, and he was honest about it. It was completely genuine. Almost everything he said made her laugh, and she spent the whole evening with a smile on her face. He was perfect, and she enjoyed every minute with him. And that kiss…. She had no words for it. It was incredible, one of the best kisses she had ever been a part of. It was so tender and loving it overwhelmed her. The night was perfect.

On the flip side, Chuck enjoyed Sarah's company immensely. She laughed at all his stupid jokes, and every time she smiled, it made him want to smile even more. He had never felt like this before, even with Jill, his ex from Stanford, who he thought at the time he loved. When Sarah asked Chuck out on a second date at the end of dinner, it was one of the happiest moments of his life. He was so excited that he got to spend another evening with her, and even more excited that they were working together. It was truly a perfect night for him.

Monday August 15th

Today was Chuck's first day at his new job. Sarah had promised to show him around the office, which made him even more excited then he was already. The idea of spending more time with Sarah was always a pleasurable one. They had texted almost all day Sunday, and because of that Chuck spent the whole day with a smile on his face.

Chuck also went to Ellie's for dinner, and told her all about his date with Sarah. She demanded that they had dinner with her sometime week. Chuck was a little anxious about having Sarah meet her overbearing sister, but excited at the same time to show her off.

When Chuck got to the office, Sarah showed him around. His workstation was on the 3rd floor, just down the hall from her office. Chuck smiled at the thought of him and Sarah working so close to each other. He could not get enough of her company. She also introduced him to his new boss, George Matthews. George was about 50 years old, 5'6-ish and bald. He looked a lot like Danny Devito, or at least to Chuck he did. He laughed thinking about how when he told Sarah about this, she didn't even know who Danny Devito was. Just more to educate her on he thought to himself, once again smiling at the thought of spending more time with Sarah.

It was around noon, and Chuck was starting to get hungry. After getting shown around the office by Sarah, he was given his first project from George, and met some of his fellow co-workers. There was Larry, who worked directly next to him. He seemed nice enough, but they didn't have much in common. Larry spent half the conversation talking about the Dodgers pennant chances, and how they might actually win the world series if Clayton Kershaw wouldn't choke in the playoffs, whoever the hell that was. Then he met Jack, who reminded him of Lester, someone who he used to work with at the Buymore. He was basically a huge sleazeball.

Lastly, there was Anthony, who he was starting to become friends with. He was tall, lanky, and a nerd like Chuck, maybe even more so. He loved video games (Anthony spent 20 minutes talking about how Counter Strike is the greatest first person shooter of all time), which was a great prerequisite for any friendship with him. He was also a bigger Firefly fan then Chuck, if that was even possible. It had been a great first day for Chuck so far.

Chuck heard his phone buzz, and saw that Sarah sent him a text.

Sarah: Wanna grab some lunch?

Chuck: Would love to

Sarah: Meet me in my office in 5? :)

Chuck: Be right over ;)

Chuck walked over to Sarah's office, and they went to lunch together. They hopped in Sarah's Porsche, and she drove them to a nearby Mexican restaurant that she loved.

"So how has your first day at Walker Corp been so far?" Sarah asked, looking through the menu.

"Pretty good. First this extremely beautiful girl showed me around, probably the highlight of my day." He winked at Sarah, and she smiled back at him. "George seems like a nice enough boss, and most of my coworkers seem OK, except for Jack. That dude is a creep."

"Yeah he is." Sarah agreed. "On my first day, he tried to hit on me. I almost broke his hand."

"Wow, hitting on the CEO's daughter on her first day. Must not be smart either." He chuckled.

"Dumb and an ass, not a great combo. Other than him, everybody is pretty nice."

Chuck smiled and nodded in agreement. "Oh, before I forget, Ellie wants you to come over for dinner sometime this week."

Sarah was excited to meet Chuck's sister. He had told her how Ellie had basically raised him after their parents left. She was happy that Chuck had someone like that in his life, a little like how she had Carina.

"I would love to. Just tell me a day and i'll be there."

When Chuck entered Walker Corp after his lunch with Sarah, he was stopped by Jack.

"Did you just go out to lunch with Sarah Walker?" He asked, dumbfounded.

"Yup."

"Wow. Are you two a thing?"

He didn't really know how to answer that, because he and Sarah hadn't actually talked about it yet. He assumed they were, due to the fact that they had basically been on three dates (if you include the night at the bar and the lunch they just had).

"Yes Jack, Chuck is my boyfriend." He heard Sarah's voice behind him, saving him from the awkward encounter. He smiled at the thought of being Sarah's boyfriend. He wasn't looking at Sarah, so he couldn't see her smile at the same exact thought.

"Wow Chuck, already trying to bang your way up the corporate ladder?" Jack asked smugly. All Chuck could do was sigh and ignore him, walking towards the elevator with Sarah.

"Thank's for the save back there." he said to her as they rode the elevator together. She responded by giving him a huge kiss, one that lasted up until the elevator doors opened. Sarah smiled and walked away from a completely frozen Chuck. Chuck finally unfroze and walked towards his work station with a huge grin on his face. He finally realized how great working at Walker Corp was going to be.