Author's Note: Hi! So, this story is about another lovable chipmunk couple! You'll find out who that couple is as you read along! Keep in mind it's the cartoon versions. I'd say they are in middle school in this story. Also, I want to thank SPARK187 for helping me come up with the title of this chapter. Everyone should know my disclaimer by now. Don't forget to leave comments!

Eleanor was in her room, standing in front of her dresser mirror. She was putting last minute touches on her make-up. She applied the mascara lightly onto her eyelashes and swiftly brushed her cheeks with a small amount of blush. Unlike her older sister Brittany, Eleanor believed that the key to using make-up is to apply it subtly. After placing her make-up brush down on her dresser, she looked over her appearance. Though the blond haired chipette was not as skinny as her older sisters, her light green top and denim shorts complemented her body shape well.

I know I'm not fat, she thought, but why can't I be skinnier?

Eleanor sighed softly as she continued to stare at herself. Her eyes were soon drawn to a picture stuck inside the frame of the dresser mirror. She reached over with her hand and took the picture out of its place in the frame to get a better look at it. She smiled as she remembered the day it was taken.

It was a year after the Chipettes met the Chipmunks. It was summer, and the whole gang decided to spend a day at the lake. Alvin and Brittany were fighting, as usual, and Simon and Jeanette were sitting on the edge of the dock talking. She and Theodore were standing near the edge of the lake, attempting to catch fish with their hand-made fishing pole, a thin string attached to a long branch. As Eleanor was fishing, she felt a tug at the line. She had caught one, and with all her might, she attempted to pull the fishing line up out of the water. Unfortunately, the fish was too strong for her, and in the blink of an eye, she was pulled into the water with a splash. When she broke the surface, she wiped the water out of her eyes and looked at Theodore. He was crouched down laughing out loud about the event that had just occurred. She could see the tears form in the corner of his eyes he was laughing so hard. With a feeling of fury in her heart, she pushed herself out of the water enough to grab Theodore's arm and pull him into the water with her. When Theodore came up to the surface, Eleanor began splashing him, laughing as she did so. Theodore in return splashed her as well also laughing. The two chipmunks were so engrossed in their splash fight they didn't even realize the commotion they were making. Brittany had the camera in hand, and during the splash fight, she had taken the snap shot.

The memory of that day always brought a smile to Eleanor's face. When she met Theodore, they became fast friends. They did everything together, cooking, and hanging out at the movies, eating out, and getting ice cream. He had been her best friend for years, and as the years went by, she grew more attached to him. She began seeing things about him she never noticed, like how he had the cutest way of sticking his tongue out whenever he was writing something down, or how concentrated he looked when he was measuring out ingredients for a recipe in Home Economics.

She didn't know when exactly she fell in love with Theodore Seville. All she knew was she had. As Eleanor placed the picture back inside the frame of the mirror, she looked at herself again, almost dissatisfied.

I'm not that bad looking. Am I? She thought.

She sighed deeply.

I just wish Theodore liked me the way I like him, she thought. I have been dropping hints for him to ask me out all year, but he's never noticed or even attempted to ask. I just wonder if there is something wrong with me.

"Ellie, come on!" Jeanette shouted from the bottom of the stairs. "We've got to meet the boys for school!"

"Coming!" Eleanor shouted back as she straightened her top.

She bent over next to her dresser, picked up her back pack, and slung it over her shoulders. She began walking out of the room, but stopped when she reached the doorway. She turned to look at the picture again.

Maybe today will be different, she thought.

With that thought in mind, she turned off her bedroom light and left her room.

Theodore stood in front of his dresser mirror and slipped on his favorite green polo shirt. When he pulled the shirt down over his stomach, he looked at himself in the mirror. He noticed his collar didn't look right. He took another look and realized his shirt was on backwards. He sighed in frustration.

"Come on," he said to himself as he fixed his shirt. "Get it together."

Once his shirt was on correctly, he looked in the mirror again. He combed his fingers through his hair and tried to give himself a more "Alvin-ish" look. Unfortunately, he just couldn't pull it off. He quickly straightened his hair back to the way he had combed it that morning.

Maybe I should practice my greeting, he thought.

"Hey, Ellie," he said in front of the mirror. "No, too informal. Hi, Eleanor. No, too formal."

Theodore turned away from the mirror and continued to ponder about his greeting. He turned back around and said, "Why hello, Ellie! Aren't you one hot chick?"

Theodore stared at his reflection in disbelief.

"Why did I just say that?" he asked himself. "That's no way to talk to a girl. Alvin must be rubbing off on me."

Theodore continued to stare at himself. There was one more thing he needed to practice.

"Hi, Ellie," he began. "I was just wondering. Would you, um, like to go out with me sometime?"

"Why, Theodore, I'd love to," said a girlish voice.

Theodore quickly turned around to see Alvin, who was making kissy faces, in his doorway.

"I would love to go out with you, my little butter ball," Alvin said, imitating Eleanor's voice.

Theodore's entire face felt hot as Alvin began to make smooching sounds with his lips. Alvin placed his arms around himself and turned where his back was facing Theodore.

"Oh, Theodore," he said in a higher pitched voice as he continued making kissing noises.

"Alvin, get out!" Theodore shouted as he took his pillow and threw it at his older brother.

Unfortunately, he hadn't thrown it quick enough, and Alvin was able to dodge it.

"Missed me!" Alvin cackled as he made his way back to his bedroom.

Theodore turned to face the mirror again.

"Come on, you fraidy cat," he said as he stared at his reflection. "You're Theodore Seville for crying out loud. You can sing in front of millions of people, but you can't ask a girl out?"

He continued to stare at himself for the longest time before he closed his eyes and took at deep breath.

But this isn't any ordinary girl, he thought. This is Eleanor Miller, the smartest, funniest, sweetest, prettiest, and most extraordinary girl I have ever met in my life.

Theodore's thoughts were disturbed when a light knock came from his door. He turned around again, expecting to see Alvin making more kissy faces at him. To his surprise, Simon stood in the doorway.

"Hey," he greeted.

Theodore didn't respond. All he did was turn back around and look in the mirror again. He listened attentively to Simon's footsteps as he walked into his room. Then, he felt his hand on his shoulder.

"Are you alright?" Simon asked.

Theodore slowly let out a breath.

"No," he said. "I'm scared to death. What if she says no?"

"I don't think Eleanor will say no."

Theodore turned his head to look at his bespectacled brother.

"How do you know?" he asked.

Simon spoke honestly and clearly.

"I know because you're the kindest, gentlest person she's ever met. You always treat her well, and trust me, she likes you."

Theodore couldn't help but smile at Simon's thoughtful words.

"You really think so?" he asked.

"I know so." Simon responded. "Remember, asking a girl out is like getting into a cold pool. You take a deep breath, and then, you jump right in. Just take it easy."

"Thanks."

Simon chuckled slightly as he began to leave the room.

"Anytime, little brother," he said.

Once Simon was gone, Theodore looked at his reflection again. The past year had been agonizingly painful for Theodore. He had tried numerous times to ask Eleanor out on a date, but every time he got the chance to ask her, he was interrupted, or he would chicken out because he as either too shy or just too scared.

"Not today though," he said out loud. "Today will be the day. I will ask Eleanor out, and nothing and no one is going to stop me."

At that moment, the door bell rang. Theodore listened as the front door opened.

"Alvin, Simon, Theodore!" Dave shouted. "The girls are here!"

"Coming, Dave!" yelled Simon as he walked down the hallway with his back pack on his shoulders.

Alvin soon followed, and Theodore knew everyone was waiting on him. He looked at himself in the mirror one last time.

"Today is the day," he said. "Don't chicken out. Just take a deep breath and ask her."

Theodore bent over, grabbed his back pack, and slung it over his shoulders. He walked out of the room quickly, turning off his bedroom light as he did so.

After briskly walking down the hallway, Theodore began climbing down the stairs. As he made his way into the living room, he heard many different conversations. Alvin and Brittany were, once again, arguing about who was the better singer. Sometimes, Theodore wished they would just kiss already. It was pretty obvious that they both liked each other, even if Alvin and Brittany wouldn't admit it. Simon and Jeanette were discussing plans for their next science project. Every time a project was assigned, Simon would always ask the teacher if he could work with Jeanette, which the teacher always agreed to. Theodore knew Simon really liked Jeanette, but when it came to girls, Simon was the same way he was, shy.

Then, his eyes caught sight of the Eighth Wonder of the World. He stopped dead in his tracks when he saw Eleanor. Though her clothing wasn't dressy, he could still drink in her simple curves and slender legs. Her hair cascaded down past her shoulders like a waterfall, and Theodore could feel his heart rate increase tenfold. What he loved most about her was her eyes. They were always a deep chocolate brown color, and every time he looked into them, he could see everything, her gentle soul, kind heart, and her natural inner beauty.

How could anyone be so beautiful? He thought.

Eleanor heard the sound of footsteps, and she quickly turned her head towards the direction of the noise. She smiled widely when she saw Theodore standing on the other side of the room, and she could feel her heart beat a little faster. He always had a strange way of doing that to her, even when he wasn't trying. She began walking towards him.

Theodore watched as Eleanor approached him. He could feel drops of sweat roll down his forehead.

Take it easy, he thought. Don't be nervous.

"Hi, Theodore!" Eleanor exclaimed once she reached Theodore.

"H-H-Hi, Eleanor," Theodore said quickly.

Pull yourself together, you worthless chipmunk, he thought.

"I'm really excited about Home Ec. today," she said. "Aren't you?"

"Um, yeah, definitely," he shyly said.

Eleanor seemed to notice Theodore's nervousness.

"Is something wrong, Theodore?" she asked worriedly.

"Um, no, not at all," he hesitantly replied.

There was a slight pause before Theodore decided to continue.

"Ellie," Theodore said.

"Yes, Theodore?" Eleanor asked curiously.

I can do this, I can do this, Theodore thought.

"I, um," he began. "I just wanted t-to, um…"

Before Theodore could finish his sentence, Dave walked into the living, causing all the conversations to stop.

"Okay, kids," Dave said. "It's time for school. Come on, everyone. Let's go."

Darn it! Theodore thought.

"Okay, Dave," all six chipmunks sang.

Soon, Dave and the six chipmunks made their way out the front door and into Dave's car. The whole ride to school, Theodore was very upset. He had finally built up enough courage to ask Eleanor out, but Dave had to ruin it. He knew he wouldn't be able to ask her in the car. For one, Alvin and Brittany's argument turned into a fully fledged war zone, and they shouted pretty much the whole trip to school. Second, he didn't want Alvin making fun of him again like he was that morning. The last thing he needed was to be embarrassed.

Theodore looked over at Eleanor, and once again took in her simple yet incredibly beautiful appearance. He couldn't help but stare as he watched her tuck a strand of loose hair behind her ear. He sighed in contentment and placed his head in his hand.

Before he knew it, they made it to school. Alvin burst the car door open and hastily began running towards the school.

"Race you inside, Brittany!" he called.

"You cheated!" she yelled as she began to run. "That's not fair!"

Dave shook his head lightly, and Simon and Jeanette exited the vehicle as well.

"Thanks for the ride, Dave," Eleanor said as she got out of the car.

"You're welcome, Eleanor," Dave said. "I hope you guys have a great day."

"Thanks, Dave," Theodore said as he too got out of the car. "I'll see you at home."

Once everyone was out of the car, Dave began to drive down the road.

"Bye, kids," he shouted.

"Bye!" Eleanor and Theodore shouted in unison.

As the two chipmunks began walking towards the school, Theodore felt as if he were going to throw up. He was standing next to the prettiest girl in the world, and he was about to ask her out. More sweat dripped from his brow. He hoped there wouldn't be any more interruptions.

"Hey, Ellie," he said gaining courage.

"Yes," she responded.

"I wanted to ask you something earlier."

"Oh, that's right. What was it you were going to ask?"

Theodore was about to continue, but once he gazed into those chocolate brown eyes, he became speechless.

"I-I-I, um, uh," he stuttered. "Um, uh, uh, would y-you, uh, um…"

Before Theodore could continue, the bell to first period rang.

"Oh, sorry, Theodore, I have to go," Eleanor said. "I can't be late for history again. Just ask me what you want to ask me later. Okay?"

"Oh, um, okay," Theodore said sadly. "Bye, Ellie."

"Bye, Theodore."

With that said, Eleanor began running towards the school. Theodore watched as she disappeared out of sight.

Ugh! I was so close, he thought. She was right there. That stupid bell. Why did it have to ring? Ugh!!

Theodore looked down at the ground and sulked as he began walking towards the school building. He didn't care that he may get in trouble for being late. His heart was hurting too much for him to care much about anything at the moment.

"Come on, perk up," he whispered to himself. "The day is still young. I'm sure I'll be able to ask her out soon."

With that thought in mind, Theodore smiled slightly and began running inside the school building.

Maybe I can catch her at lunch, he thought.

In this case, it wasn't "saved by the bell" for Theodore. So, will he ever get a chance to ask Eleanor out on a date? You'll just have to wait and see. Hoped you liked the first chapter.