A/N: Hi everyone! So, I know I always start new stories before I finish any of the ones I'm already writing, but I just can't keep my ideas inside. I have a need to let them out before I burst! I promise I will finish my other stories, I'm not going anywhere. This one is based on the movie Definitely, Maybe starring Abigail Breslin and Ryan Reynolds. It's one of my absolute favorites, and I thought it would make for a fun Chuck fanfic! I'll try and throw in some hints here and there, but it's really a guessing game for all of you. Let's see who can figure out the mystery first!

-Charahfan44


PRESENT DAY

I don't often ask my parents for anything, especially now since they are going through a separation. They told me a few months ago, and we've all been trying to adjust since then. Every two weeks, I switch off to another parent. The first two weeks of the month I spend with my mom, and the last two with my dad. It's not exactly the dream scenario, but I'm glad to have them both. Today, it was my dad's turn to pick me up from school, starting our two weeks together. He was as chipper as usual, which always lightened my mood.

"Hey, kiddo." He smiled as I opened the car door.

"Hi, dad." I smiled back, jumping in.

"How was school?"

"The same as it always is." I buckled myself in. "I'd really like to be in high school already." I added.

"One more year. It'll go by fast, trust me." He replied. I had just started my last year at the junior high, and I wasn't exactly loving the eighth grade.

"You always say that, and then time seems to slow down." I sighed.

"Trust me, I'm usually right." He joked. "How was your two weeks with mom?" He asked. At first, I didn't mind when they each asked me about each other, but now it was starting to get annoying. Every time I switched off, they would sneak in a question about the other.

"Fine." I responded. I had decided to start keeping my answers short and sweet. Maybe this way, they'd start talking again.

"Well that's better than bad." He laughed. "What do you want for dinner tonight? I haven't had time to go to the store this week, so we'll be ordering in."

"What do you feel like?" I hated making decisions, which is something I didn't develop from either parent.

"Let's go with Chinese."

"Sounds like a plan." The rest of the drive was silent in conversation. Dad and I liked to listen to the radio together, humming or singing along with the melody. When I was younger, we'd put on little concerts in our living room, mom video taping every single one. Little did I know, they'd use the videos to embarrass me at an older age. It didn't take us too long to get home, as dad's new apartment was only a few blocks from the school.

"Get started on your homework, and I'll call in to Bamboo Dragon." He said, putting his keys and work bag on the counter of the small kitchen.

"Aye aye, captain." I replied, sitting down at the living room table. I hated how tiny his apartment was, but knew that he was still holding out hope to move back home with mom and I. Before they split, they had been fighting a lot. I wouldn't be able to sleep because they're voices were so loud. At one point, I had to go into their room and break up the shouting match. I think it was that point in time that they realized they needed a break from each other. I stared at my math homework, unable to make sense of the numbers and symbols. I wasn't great with math, and my crowded mind wasn't helping.

"What are you working on?" Dad's voice loomed over my shoulder.

"Algebra." I said.

"I loved algebra when I was in school." He said excitedly.

"Makes one of us." I groaned.

"Need some help?"

"Please." I replied. He sat down next to me, and helped me with each problem I didn't understand. Our food came almost forty five minutes later, and we ate it like we had never eaten anything in our lives. He always made sure I was in bed by ten o'clock.

"You good?" He asked from the doorway.

"Yes." I said with a hint of annoyance. I hated it when he tried tucking me in like a child.

"Okay, okay," He put his hands up in surrender, "Just checking." He turned to leave.

"Hey, dad?"

"Yeah?" He turned back to me.

"Can I ask you a question?"

"Always." He smiled.

"Can I hear the story about you and mom?"

"What story?"

"The whole story. Everything that led up to this moment." I held his gaze.

"What prompted this?"

"I don't know, I just still don't understand why you guys aren't together." I looked away briefly.

"Even with a story, I won't understand it myself." He admitted. "But I can tell you if you really want to know."

"Okay." I felt my face light up. "Did you ever date anyone else?"

"What?" He laughed nervously.

"You know, was there anyone else before mom?"

"Sure, I had other girlfriends." He shrugged, coming over to sit at the edge of my bed. "Tell you what, I'll tell you the story of my three most serious girlfriends, and you have to guess which one is your mom."

"But I know mom's name." I laughed.

"Okay, I'll change the names." He said.

"Deal." We shook on it playfully, and I settled into my bed comfortably.

"Okay, let's start with the summer of two thousand."


August 24th, 2000

Chuck Bartowski was one of a kind in every way. He was the nicest guy around, and most people knew who he was. His best friend, Bryce Larkin, was considered the big man on campus, but he made sure Chuck had some popularity as well. Today was the first day of sophomore year at Harvard, and everyone was already bustling around the campus. Chuck, being his usual self, was busy looking down at his class schedule, when he bumped into someone.

"Watch it!" The voice shouted, obviously upset.

"Sorry, I didn't notice you." He mumbled, picking up the book the stranger had dropped.

"Obviously."

"I really am sorr-" He stopped short, looking up at the person. She was the most beautiful woman he had ever seen. Something about er struck him hard, causing him to lose any word he had in his mind.

"Did you hit your head or something?" She asked snottily.

"Uh, no." He handed her the books. "I just...you..."

"Maybe you should put some English classes on your list." She rolled her eyes.

"Yo, Chuck!" Bryce's voice sounded from behind. "We've got to go."

"Bryce Larkin." The girl looked in the direction of Chuck's best friend.

"You know Bryce?" Chuck asked.

"I know of him." She replied.

"Well hello there." Bryce put on his charm as he approached the two. "Are you new here?"

"How'd you know?" She asked.

"I definitely would've remembered seeing someone as beautiful as you." Bryce replied, flashing his famous mega-watt smile.

"I'm Kate." She reached her hand out for his.

"Kate. I like that." He gladly shook her hand back. "Sorry to interrupt this little meeting, but Chuck and I have to go."

"I'm sure we'll see each other around." Kate smiled.

"I'm betting on it." Bryce winked. "Catch you later, Kate." Bryce watched as she walked away, admiring her beauty.

"I ran into her." Chuck winced. "Literally."

"Damn, a girl like that doesn't just waltz into your life for nothing." Bryce kept his eyes on Kate. "But hey, we have a frat party to host tonight."

"Really?" Chuck groaned. "I told you, I'm not into the whole party thing."

"It'll be fun, I promise."

"Why didn't you invite Kate?" Chuck asked, wanting to see her again.

"I definitely want to wine and dine her, you feel me?"

"Sure." Chuck shrugged.

"It's okay, Chucky, we'll find you a girl tonight."

"How about I stay single and focus on school?"

"Chuck, college is the time for bad choices. You should let yourself have some fun."

"Maybe someday." The two walked to their dorm room, and settled in for the next few hours. Bryce was constantly checking himself out in the mirror, but Chuck didn't mind. At the end of the day, Bryce still played video games and ate junk food, and that's all Chuck could hope for.

"Dude, we have to leave in like, twenty minutes." Bryce had finished getting ready by ten o'clock that evening.

"I think I'm coming down with the flu." Chuck forced a cough.

"Get your party clothes on, you're going." Bryce said. He always forced Chuck to leave the room and have a good time. They got to the frat house in less than ten minutes, Bryce lighting up the place as he walked in. "The party has arrived!" He threw his hands in the air, causing everyone to erupt with cheers.

"Nice place you got here." Chuck jokingly said to the bobcat statue next to the doorway.

"Dude, who are you talking to?" One of the frat boys looked at him with disgust.

"Uh, myself." Chuck scratched the back of his head before following Bryce to the drink table.

"What're you having, Chuck?" Bryce asked.

"Water is fine."

"Rum and coke it is."

"Seriously, I don't need a drink."

"Seriously, yes you do." Bryce handed him a cup. "Drink up, science boy."

"Fine. But just this one." Chuck sipped on his drink lightly, getting abandoned by Bryce almost immediately. Chuck was sure he was off flirting with a beautiful woman, because that's what he did best. He made his way out to the balcony, already looking for fresh air.

"Looks like we're the losers stuck out here with no one." A familiar voice said behind him. He whirled around to see Kate holding a drink in her hand. "You." She recognized him in a heartbeat.

"This isn't awkward." He said sarcastically.

"There's no going back now." She stood beside him, peering over the bars on the edge.

"I didn't really take you for a party girl."

"You don't know me at all."

"True." He looked down below. "I've just been yelled at by you."

"Whoa, wait a minute." She looked at him. "I did not yell. I merely raised my voice because you ran straight into me."

"Maybe if you had been looking, you would've avoided me." He sassed back.

"You're basically a wall, no one can avoid you." She laughed.

"Wow, a smile?" He laughed back. "What a rare surprise."

"I'm not a total bitch. Just a tiny one." She took a drink from her cup. "So, you're friends with Bryce?" There it was. The one question that all women asked him.

"Yeah."

"Is he seeing anyone?"

"He's seeing everyone." Chuck mumbled.

"You think you could put in a good word?" She asked.

"I'd love to."

"Thanks, uh..." She trailed, forgetting his name.

"Chuck." He said flatly.

"Right, Chuck." She looked at him guiltily. "I should probably get back in there. See you around?"

"See you around."


PRESENT DAY

I was falling asleep as dad told me the story, but I desperately wanted to hear more.

"What?" I raised my voice. "She used you to get Uncle Bryce?" I asked.

"I wouldn't say 'used'." He replied with a laugh. "She just didn't have feelings for me yet."

"I can't believe you let this woman become a serious girlfriend." I shook my head. "She definitely doesn't sound like mom."

"You never know." He said slyly.

"So this Kate lady is mom?"

"I didn't say that." He kept his mysterious tone. "I said you never know."

"Okay, this so isn't fair."

"You shook on it." He joked.

"Yeah, but I didn't shake on you confusing me." I pouted.

"Just wait until I tell you the whole thing, and then you can tell me who you think your mom is."

"What happened after the party?" I asked.

"We'll have to hear about it tomorrow." He smiled, kissing my forehead softly before getting up to leave.

"You can't leave it like that!" I whined.

"Sure I can." He winked. "Get some sleep." He turned my light off, shutting the door softly. That night, I couldn't sleep at all. He had only told me a tiny portion of his story, and yet I had thousands of theories swirling through my mind. I wanted to hear the next part so badly, only because I wanted to hear about the other two. At eleven o'clock, I looked to my phone, and dialed my mom's number.

"What are you still doing up?" She didn't sound happy that I was awake.

"Can't sleep." I kept my answer short.

"You okay?" She asked.

"Yeah, I'm just thinking about stuff."

"What kind of stuff?"

"I really wish I didn't have to stay here." I sighed.

"I know." Her reply seemed sad. "But, you need time with your dad too."

"I didn't mean here with dad, I meant here period. We should both be at home."

"We've talked about this."

"I know. It's still hard."

"It will get easier."

"Doesn't seem like it."

"You should go to bed, okay? Enjoy the weekend with your dad." She changed subjects.

"Okay."

"I love you." I could hear the empathetic tone in her voice. She knew that their decision affected me heavily, but she wouldn't change her mind.

"Love you too." I said back. I hung up, finally feeling tired. I wasn't the type of person to ever realize when I fell asleep, so it always felt weird waking up. When I woke up the next morning, I was on my dad's case before he even had time to think.

"What happened next?" I asked, watching him make omelets.

"Can we at least eat breakfast first?"

"You said you'd tell me more tomorrow, and tomorrow is now." I sat at the dining room table in front of the kitchen area, unable to hide my excitement.

"You are my kid, aren't you?" He laughed, shaking his head.

"Obviously you and Kate dated, or you wouldn't be telling me about her. I want to hear how you guys got together!"

"It took a long time for us to get there."

"Good thing we have lots of time."

"Fine," He brought a finished omelet over to me, "I'll continue."

"Great." I smiled. "So, after the party." I reminded him.

"Right. After the party."


October 3rd, 2000

Only a few months had passed since Chuck and Bryce had first met Kate, and now they spent every moment together. Bryce and Kate had obviously developed an intimate connection, one Chuck could've only dreamed of. He spent most of his off time studying in the library, mostly due to the fact that he didn't want to see his crush and his best friend all over each other.

"Thought I'd find you here." Kate's voice caused him to look up from his anatomy book.

"Oh, hey." He looked back down almost immediately.

"What a greeting." She joked. "You busy?"

"Sorry, I just can't get a bad score on this test." He sighed.

"Want some help? I actually understand quite a bit." She sat across from him at the table.

"Right, I forgot we have the same class."

"Forgot? We sit next to each other." She laughed. "You okay?"

"I'm fine, just stressed."

"Bryce said you'd been acting weird the past few weeks."

"Yeah."

"Maybe what you need is some time away from school." She said.

"What do you mean?"

"You never get away from campus, maybe you should." She shrugged.

"My entire life has been about getting into this school, Kate. I can't slack off now." He replied.

"I'm not saying you need to slack off, all I'm saying is that maybe you deserve a night off."

"Oh yeah? And where do you suggest I go?"

"There's a really fun mini golf course that Bryce and I were planning on going to tomorrow. You should come!" She smiled.

"What a fun night that sounds like." Chuck said facetiously.

"You know, I have a friend that totally loves guys like you." She added. "I think you'd like her."

"I don't know..."

"Please? I want you to come. Let me set you up, I promise you'll have a good time."

"Fine." He looked at her, feeling a smile form on his face, mimicking hers.

"Good. Tomorrow night, at six." She got up just as quickly as she had sat down. "Oh, uh, would you mind hanging out here for a bit? Bryce and I will be in your room and I don't want you to walk in on...anything." She added the last part sheepishly.

"Sure, no problem." Chuck pretended to be cool.

"Thanks, Chuck, you're a really good friend." She smiled once more before leaving the library. Chuck sighed, looking back at his anatomy textbook. He stayed there for a few hours, not wanting to interrupt anything that may have been happening back in his room. He got home around seven, and was relieved to find the room empty. The next day went by quickly, and he passed his anatomy test with a ninety-one percent. Kate came over before the double date, checking in on Chuck.

"I don't think I can do this." He said, struggling to pick out a shirt.

"Chuck, you're going to be fine." She laughed. "But not if you wear that." She gave his ratty Harvard shirt a disapproving look.

"Help." He begged. Kate bee lined for his closet, picking out anything she thought would pass for a date.

"Here, put this one on." She handed him a dark blue button up.

"If I look like an idiot in front of this stranger tonight, I'm not going to talk to you ever again." He said, putting on the shirt.

"That's definitely the one." Kate smiled, watching him check himself over in the mirror.

"We ready to go?" Bryce entered, holding a six pack.

"Doesn't he look good?" Kate asked her boyfriend.

"Uh, guys don't really tell each other how cute they look." He popped open a beer, kissing Kate quickly.

"I think he looks great." She nodded.

"Thanks." Chuck smiled. There was a sudden knock on the door, and Kate answered it. A woman walked in, looking confident and completely sure of herself. She was tall, but not as tall as Chuck.

"Julia, this is Chuck." Kate led her friend into the main part of the room. "Chuck, this is Julia."

"Hi." He stuck out his hand.

"You're cute." Julia replied, shaking it.

"Uh, thank you." He scratched the back of his head nervously.

"We should go." Bryce said. The four exited the room, Bryce and Kate walking hand in hand. Chuck couldn't help but imagine himself with Kate, doing all the couple-y things people did.

"It's okay, I won't say anything." Julia whispered.

"What?" He looked to her.

"I've seen you around, looking at her like you are right now."

"I don't-"

"Oh please, Chuck. You like her."

"She's my friend."

"I'll help make you look good tonight, don't worry. Maybe we'll even make her a little jealous." She grabbed his hand and intertwined her fingers with his. This night was going to be interesting, and this was only the beginning.