Well hello there, welcome to my first, and most likely last, chipmunks story. Haha I have no idea how this thing came to fruition… it started with a few lines of dialogue, and then I wrote the ending, and then the ending needed a beginning and uh, yeah.

Recently I rediscovered the wonders of the chipmunks when I accidentally stumbled upon one of the CGI movies, which I always assumed I would hate, but then I kindof loved it, and had to watch the other two and then go back and watch all the 80's chipmunk stuff… aww yea. Chipmunk love. In this story, they shall be their original 80's selves.

Also when I was little and obsessed with this show I wanted to marry Alvin, but now I find myself being more drawn towards Simon- I have no idea how my 5 year old self never noticed how adorable that nerdy know-it-all awkward little bro really was. And Jeanette. She is just perfect. Put her together with Si and you get shy nerd love, which is just the ultimate couple. A thousand times yes to simonette.

So I wrote them their own story. Nothing too long or intense… I'm guessing it'll probably be 3 or 4 chapters total? I've written the beginning and the ending and I know what'll happen in the middle so we'll see.


Simon Seville was currently in a state of intense concentration. The 15-year-old chipmunk sat at a desk in the room he shared with his two brothers, and was hunched over a thick textbook, his nose buried deep within the pages. His large front teeth were absentmindedly chewing on his bottom lip, his hand occasionally scrawling things into a separate notebook nearby. In short, Simon was in study mode, and oh, how he reveled in getting to be in study mode.

The room was quiet, just how the boy liked it. Only because his aforementioned brothers, Alvin and Theodore, had left late morning to watch Eleanor Miller's soccer game. Eleanor was a member of the chipettes—3 sisters who were long-time friends of the chipmunks—and Theodore's girlfriend. She was also exceptional at soccer, making any game she played in an exciting one. This was part of the reason why the eldest chipmunk wanted to tag along too, but it was probably mostly because Brittany Miller, best friend of Alvin and eldest of the chipettes, never missed one of Eleanor's games, and Alvin never ever passed up a chance to annoy Brittany.

Simon had declined the invitation to join, because the thought of an empty house was all too appealing to him. Around noon, the middle Seville child had decided to snatch up the fleeting calm to get some work done. Unlike his siblings, the bespectacled chipmunk was not above doing homework on a Saturday; in fact, he quite enjoyed it, although he could never mention this fact aloud without people making fun of him.

Well, not all people. His best friend, Jeanette Miller, definitely was not among those who would make fun of his studious habits. In fact, he would be willing to bet that she might be spending her Saturday afternoon the exact way he was. Just one of the many things he really, ah, appreciated about his female companion.

What had once been meticulous notes turned to absentminded scribbles as thoughts of Jeanette slowly began their infiltration of the young chipmunk's mind. He wondered what she really was doing at the moment, and how soon they could hang out again. He thought about how he, Jeanette, his brothers, and her two sisters had gone to the arcade yesterday after school. He and Jean had played a few rounds of air hockey there, and his brain was presently replaying the way she giggled whenever she managed to score a goal on him. A lazy smile somehow made its way across his face.

A few moments later, Simon blinked and awakened from his Jeanette-induced stupor. Looking down, he realized his pencil had unintentionally lazed across the page to form a doodle that greatly resembled the object of his affectionate thoughts. The teen groaned at the embarrassing evidence that he'd been thinking about Jeanette yet again. She was probably the one of the few things that could break his concentration like this, but it was only because she was such a kind, easygoing, genuine person whom he maybe happened to like-like a little.

Okay, he had a massive crush on her. Simon wasn't really one to be in denial about his own feelings—not that he would ever tell her about them.

It was hard to isolate the exact point when the he'd started to develop feelings for his brunette best friend, but if he had to guess, it was probably towards the end of middle school, a little bit of time after the scholarly boy had come up for air from his studies long enough to discover that while before he'd found girls interesting, now he found them… very interesting. After this discovery, he often found himself dwelling on the little detail that a certain chipette, whom he already spent a lot of time with, was, in fact, a girl. A very pretty girl. A very pretty girl whom he had a lot in common with and had a wonderful personality.

Well, it had all gone downhill from there.

Now the chipmunks and chipettes were all starting out their sophomore year of high school, and Simon had yet to clue Jeanette in to the fact that he wanted to be more than just friends with her. The trouble was, Simon's expertise was science and academia, not relationships. He had no idea how to go about letting her know how he felt without being completely awkward about it. Plus there was the pretty important matter of whether she reciprocated or not; jeopardizing what they had now really wasn't worth it if there was a chance that spilling the beans could cause their entire friendship to go up in flames.

Simon removed his glasses and tiredly cleaned them on his dark blue button up shirt, trying to return his thoughts to the world history textbook before him. He'd only managed to read a few more paragraphs before he heard rumbling on the stairs, and the door banged open a few seconds after, revealing his missing siblings. Alvin was slurping down what looked like a milkshake, while the youngest of the three was holding two of the sweet treats in his hands.

"Hi Simon!" Theodore chimed, walking over to the desk and holding one of the milkshakes out for the blue-clad chipmunk to take. "Here, we got this for you on our way home from the park."

Simon gratefully accepted the gift. "Thanks, Theo." He took a sip—ah, mint chocolate chip. His brothers knew him too well. "How was the soccer game?"

"Ellie's team kicked butt!" The plump boy dressed in green pumped a fist in the air. "She was amazing! She even scored two of the goals!"

Simon smiled. "That's great!"

Alvin, who was still by the door, parted from his milkshake long enough to make a skeptical face. "Si, don't tell me you've been sitting here doing homework the entire time we were gone," He said in lighthearted annoyance.

The boy in the glasses crossed his arms and wore a haughty expression. "Not… the entire time."

"Oh, brother." Alvin stalked over to the desk and set his milkshake down. "It's a Saturday for pete's sake! Homework on a Saturday is strictly forbidden! Y'know, you really need to learn to live a little. "

Simon rolled his eyes. "I happen to be living just fine, thank you."

"Sure, of course you'd think that."

From there, an argument was born. It happened at least once a day, and Theodore, who'd long ago learned to ignore and keep out of his elder siblings' little spats, decided to direct his attention to a curious little drawing in the notebook on the table. A good-natured smile appeared between his chubby cheeks. He tapped who he knew to be the artist on the shoulder.

"Hey Simon, is that a drawing of Jeanette?" He asked innocently. "It's pretty good!"

"What? No!" The usually most composed one of the three boys flushed a light shade of pink, realizing his mistake of leaving his notebook out in the open too late. Already a quick-witted Alvin had grabbed the object in question and dashed away to the center of the bedroom to examine it. After a second the red hat-wearing teen sported an evil grin and a sickeningly knowing look. Simon could only let his head fall to the desk with a defeated thud, groaning in embarrassment.

"This is what you've been doing all day? Drawing pictures of Jeanette? Ha ha!" The teasing chipmunk slapped a hand to his forehead and laughed.

"Just give it back, Alvin," Simon growled.

Taking pity on his little brother, Alvin conceded and snapped the notebook shut, handing it back, still chuckling all the while. "You know Si, instead of just sitting here in pathetic lovesickness, maybe you should actually do what normal people do and make a move."

Simon scoffed. As if it was that easy. "I am not lovesick." He said meekly. Alvin and Theodore shot each other looks. "I saw that! Okay. So I like Jeanette a little. You both already knew it."

"A little?" Theodore quirked an eyebrow, causing the blushing chipmunk in front of him to rise out of his seat and start pacing in the center of the room.

"Oh, whatever! I can't just 'make a move,' as you so eloquently put it." Simon gazed sheepishly to the floor. It was hard for him to make admissions such as this. "I'm not… I'm not good at that sort of thing."

"Simon, Simon." Alvin walked over and slung an arm around his shoulders. "You really are hopeless when it comes to women, aren't you? As usual, you're making this a lot harder than it has to be. It's not that hard to ask out a girl. I've done it loads of times. And look at Theodore! Even he's done it!"

The green-clad boy stopped sipping from his milkshake to voice an indignant "hey!" Somewhat offended, the youngest chipmunk stalked from the room.

Simon's head was starting to hurt with all this eye-rolling he was doing. "Wasn't Eleanor the one who asked him out?" He deadpanned. Alvin waved him off.

"That's not the point. The point is that you need to man up and take action, before somebody beats you to it and steals your woman!"

"Jeanette's not my woman," Simon retorted feebly, trying not to let his brother's usually warped logic get to him. In actuality his brain was picturing horrible scenarios in which Jeanette had a boyfriend who wasn't him. Just the thought made him sick to his stomach. His heart dropped, and he sighed. "Well, what should I do?"

"Go over to her house, and ask her out on a date! Duh!"

Simon rubbed the back of his neck. This plan did not sound the least bit appealing. In fact, this whole 'make a move' business was beginning to make him queasy. How could he even begin to figure out what to say to her? "When do I do that?" he asked wearily.

Alvin clucked his tongue and shook his head in annoyance. "When do you think, genius? Right now!"

All the color drained from the brainy teen's face. "W-what! I can't just go over there right now—I-I don't even know what I'm going to say!" His head shifted crazily around the room, his glasses fell crooked, and he clutched the back of his neck for dear life. Alvin, sensing the obvious hysteria radiating off of his brother, grabbed him by the shoulders.

"Si! Snap out of it, you're going to hyperventilate!" At this Simon quieted and pushed his crooked glasses back into place with his index finger. "Since you have to have a 'well thought out plan' for everything, just make one up and then do it tonight instead."

Simon swallowed. "Tonight?"

Alvin clapped him on the back and retrieved his milkshake, taking a long, irritating slurp. "Tonight. Just walk up to her and make that move. No big deal."

With that his cocky older brother left the room, off to do who-knows what, leaving Simon to simmer in the horror of the impossibly embarrassing task that he was suddenly put up to.

Making a move. On Jeanette. Apparently to Alvin this was 'no big deal.' Right.

Oh god, he was going to be sick.


Elohel. I just love pushing awkward nerdy characters out of their comfort zones. Review if you please!