Simon's Question

Hello everyone! Finally, I'm making a new AATC fanfic! This is set years after "Jeanette's Confession". I had part of this idea last year, but thought of more stuff last night. I hope you all like this story! Also, like the last story, besides recently coming across a few scenes online, I haven't really looked at much Chipmunk content, so I hope the characters aren't OOC

Disclaimer: I only own my FCs!

Simon paced back and forth around his room. He exhaled, trying to maintain his composure. He wasn't even sure why he was so nervous. Everything was fine! Although, his brothers and their partners were taking a REALLY long time getting to his house. What was taking them so long?

Thankfully, he didn't have to wait much longer. He left his room when he heard a loud knock on the front door. Simon reached the living room and opened the door. On the other side were his brothers Alvin and Theodore, Eleanor, and Brittany, carrying her and Alvin's four-month-old daughter Cadence. The smaller chipmunk opened her eyes and looked at her taller uncle.

Simon smiled and kissed Cadence's cheek, making her smile. The fact that Alvin and Brittany were married and had a daughter still shocked him. It's been a few years since the Chipmunks and Chipettes graduated from high school. Ever since then, the Chipmunks and their girlfriends, the Chipettes, remained together. Alvin and Brittany staying together was very shocking, since the couple would date on and off over the years. Alvin and Brittany got married last year and had their daughter Cadence this year.

"Sorry we're late, Simon." Brittany said as she and the others entered the house. "Cadence has been crying all morning, and she finally calmed down."

"And Theodore and I were stuck in traffic..." Eleanor let out a sigh.

Simon chuckled as he sat down. "It's alright."

"So," Alvin took off his red hat and wiped some sweat off his forehead. "What did you wanna talk about?"

"Oh, r-right." Simon chuckled nervously. "Well, you see..."

Theodore had a slightly worried expression on his face. "Is everything ok?"

Simon sighed. "Yes. It's just... Jeanette and I have been dating since high school and..."

"And...?" Eleanor repeated.

"I hope you're not planning on breaking up with her." Brittany said.

Simon's eyes widened. "N-No!"

"Where is Jeanette anyways?" Alvin wondered.

Simon replied, "She's at the library. I wanted you guys to come over while she was out."

"Soooo, what's up?" Alvin asked.

Simon let out another sigh. "I need your help." He adjusted his glasses and looked at everyone. "I..." Simon's face grew warm. "I'm ready to get married. I wanna propose to Jeanette."

Everyone gasped as they stared, their eyes wide, at the bespectacled Chipmunk. Then, Brittany and Eleanor squealed, making the three brothers wince.

"Oh my gosh, Simon! This is so exciting!" Eleanor exclaimed.

Brittany added, "Right! Do you have a ring? When are you gonna ask her? Oh, I just know her wedding dress will be gorgeous!"

Alvin chuckled. "Babe, relax! He didn't even ask her yet, and you're already thinking about dresses."

Brittany giggled. "I can't help it! I'm excited!"

"Well, to answer your questions, I don't have a ring yet and I'm not sure when to ask her. That's why I called you all here."

Smiling, Theodore said, "We can definitely help you, Simon."

Brittany gasped, getting everyone's attention. "I got a great idea!"

Alvin raised an eyebrow. "What is it?"

"We're about to go on tour! Our final stop is Honolulu!" Brittany's smile widened. "Simon can ask her then!"

Eleanor nodded. "That sounds great!"

"Hmm," Simon pondered for a moment. "That does sound good."

"Great!" After saying that, Brittany took out her phone. "Now, let's look for some rings..."

The Chipmunks and the Chipettes were currently outside of a house. Alvin knocked on the door, waiting for the person on the other side to answer.

"One second!" They heard a voice say.

Then, a female chipmunk with long black hair pulled back in a ponytail and wearing a purple shirt, jeans, and black shoes, opened the door. The chipmunk smiled at him and Brittany.

"Hey guys!" She greeted.

"Hey Rhonda!" Alvin replied.

Another chipmunk, this one a guy, with brown hair and wearing an orange hat, an orange shirt, jeans, and black shoes, walked over and stood next to Rhonda.

"Oh, hey!" The guy said.

After giving Cadence to Rhonda, Brittany said, "Thanks again for watching her for us."

Rhonda grinned. "It's no problem! She's so adorable! Plus, this'll be good practice for Max and I for when we have our own."

Max blushed as he took the diaper bag from Alvin. "O-Our own!?"

Rhonda and Brittany chuckled at Max's reaction. The friends said goodbye and Max and Rhonda watched as the others left.

Jeanette sat on the plane by the window and grinned. She couldn't wait to visit all of the different cities. It was always so much fun visiting different places! She turned to face Simon.

"This is going to be so much fun!" She said.

Simon stared at his feet. Jeanette tapped his arm lightly and he snapped out of it.

"Huh? O-Oh, I'm sorry. Did you say something, Jeanette?" He asked.

Jeanette frowned slightly. "Are you ok, Simon? You seem like you have something on your mind."

Simon chuckled and rubbed the back of his head. "Yes. I was just thinking about everything."

Jeanette smiled again and kissed him. "Don't worry. Everything's gonna be alright."

Simon reddened. "You're right."

Everyone had a great time performing around the country. They went to many different cities, singing many songs for their fans. They went to places like New York, Washington D.C., Chicago, and even New Orleans. Simon and the others loved seeing how excited their fans got. They also enjoyed giving their fans autographs. Alvin and Brittany were the main ones to give them, but the others did give out a lot.

At last, Dave and the six of them reached Honolulu, their final destination. Brittany smiled as she looked around. Hawaii was a beautiful place, but it was much more beautiful in person! Tomorrow night was going to be their final concert and then they'd head back home. But for now, they all could relax and have fun.

After taking both of her sisters hands, Brittany headed straight for the mall.

Simon took a deep breath, trying to calm down. Unfortunately, he continued to shake. Everyone was backstage waiting for the concert to begin. Alvin walked over and whispered to his younger brother.

"Dude, relax! Everything's gonna be alright!"

Simon nodded and took another deep breath. He still trembled, but not as much this time. Then, Jeanette walked over to him after talking with Theodore and her sisters.

"Simon? You ok?" She asked.

Simon fidgeted with his glasses and smiled—too quickly. "Yeah, just... excited."

Though a little perplexed, Jeanette decided to let it go. She smiled at him and said, "Alright then. Let's continue to do our best!"

Before long, they heard the music playing and everyone walked onto the stage, smiling at their screaming fans.

During the concert, the group sang many different songs. Some old, some new. They even did duets. Alvin and Brittany sang together first, then Theodore and Eleanor. Right now, Simon and Jeanette were singing a love song together. Eleanor suggested that the two sing last, which Simon agreed.

Simon looked into Jeanette's eyes as they sang together, both of their faces turning pink. As he sang, his mind kept going to their plan.

"You can do this, Simon!" He thought to himself.

Simon and Jeanette sang the final lyrics to the song and bowed as the fans cheered.

"Thank you! Thank you everyone!" Simon said through the microphone. "Now, before we leave, there's one more thing that I need to say."

Jeanette stared at him in confusion while everyone in the audience muttered to one another. This didn't happen at their previous concerts. What was Simon doing? She glanced over at the back of the stage and even noticed the confusion on Dave's face.

The waves crashed softly in the background as Simon stepped forward, his heart racing. He took a deep breath as the crowd started to quiet down.

"Jeanette... we've toured the world together many times... but tonight, I'm hoping to begin a different kind of journey—with you."

He pulled out a tiny purple box and dropped to one knee, the lights casting a soft glow around them. Jeanette and the audience gasped as they watched him.

Simon looked up at Jeanette with a small smile. "Will you marry me?"

Jeanette stood there, stunned. Then, she smiled and tears formed in her eyes.

"Yes!" Jeanette nodded. "Of course I will, Simon!"

The crowd cheered loudly and clapped as Simon put the ring on Jeanette's finger, fireworks bursting above the ocean. Once he stood, Jeanette kissed him. Simon blushed and kissed back.

Jeanette and Simon pulled away from the kiss and hugged.

"I love you so much, Simon." Jeanette said, tears still flowing down her cheeks.

"I love you too, Jeanette." Simon replied.

As Simon wiped away Jeanette's tears, their siblings walked over to them, bringing the two into a group hug.

I hope you all enjoyed this story!