Author's Note: I hope you guys enjoy this one-shot. There's a lot of Ricky/Amy stories out there, so I wanted to focus on the other characters for a change. I don't own the Secret Life of the American Teenager (obviously) & I do not own Stupid Cupid by Mandy Moore.

Summary: Madison is 22 years old now and trying to pursue her dreams as a singer. What happens when she runs into a familiar face after her performance? One-shot.

"In our next act, we have Madison Cooperstein, performing Stupid Cupid!" The speaker shouts as he adjusts his clip on tie. Everyone claps their hands together, some even shouting for Madison.

Madison never thought she would get to this point, where she could be free, and happy, and where she feels like she's making the right decision. It took four torturous years at Grant High for her to grow up. After sleeping with Jesse, Madison learned that sleeping with guys who mean nothing to you just to feel good about yourself is wrong. She learned the consequences of it all, and that's when she realized that her and Lauren would never be friends again because of what she did. Eventually as she grew older, she began to cut out all of the people she knew in Grant High. It was the easiest way for her to work on herself and start becoming mature about the situation.

She walks onto the stage, her hair curled to perfection. It seems to be an even brighter red and her face glows as she smiles at the audience. Her body's thickened out a little more and she has curves yet her face looks as youthful as when she was still in high-school. Being on the stage makes her happy, and when she's there, she never wants it to end. People never thought much of Madison, but when she starts singing, they think the world of her.

"I hope you guys enjoy tonight. Let's give a hand for our lovely speaker." She says, giving him a quick one armed hug as the audience gives him a brief clap. The music begins and Madison closes her eyes, feeling the beat of the music take over her. She opens her mouth, releasing her heavenly voice from her lips as she sings.

Stupid cupid you're a real mean guy

I'd like to clip your wings so you can't fly

I am in love

And it's crying shame

And I know that you're the one to blame

Hey hey, set me free

Stupid cupid, stop picking on me

As she sings her song, she can see the audience smiling at her. Some of the elderly people stand up and start dancing, and she chuckles at this as she continues to sing.

Can't do my homework

And I can't think straight

I meet him every morning bout a half past 8

I'm acting like a love sick fool

He's even got me carrying his books to school

Hey hey, set me free, stupid cupid stop picking on me

Madison snaps her fingers to the tune, her red hair bounces as she moves from side to side of the stage.

You've mixed up good right from the very start

Hey go play robin hood with somebody else's heart

You've got me jumping like a crazy clown

And I don't feature what you're putting down

Since I kissed his loving lips of wine

The thing that bothers me is that I like it fine

Hey hey, set me free stupid cupid stop picking on me.

She finishes up her song, earning a standing ovation from the audience. She smiles, "Thank you so much everyone!" Then she exits the stage.

"Great performance today." A few people tell her and she thanks them warmly. She grabs her coat, already thinking about her plans for the next day when she sees someone that she hasn't seen in a while. Her jaw practically drops to the floor, "Jason?" She questions, almost mumbling the words.

She looks him up and down. He's taller now, with the same chocolate colored skin and shaved hair as before. He's wearing a leather jacket and a blue shirt with some jeans. He turns around, trying to figure out who's called him.

No backing down now. She says to herself, her heart fluttering with each step. She's nervous, because in all honesty she never truly got over their break up. Sure, she had been with other guys after Jason, but she realized just how mature and good hearted Jason had always been. When they broke up, she remembered his exact words, "I'm sorry Madison, but you're just too casual about your future for me." Although she didn't understand it back then, she understood now. Even though she was just a freshman at the time, she didn't have a future plan like everyone else, and she still didn't have one, but it was different now. She wasn't focused on boys, she was focused on figuring out her life, much like he had been when they dated.

"Madison?" He says, his eyes widening upon seeing her.

She lets out a nervous laugh, then nods, "After all these years...It's crazy how small this world is eh?"

"Uh, yeah. It is. You look...great Madison, really great." He says with a smile, looking her up and down.

"Thanks," she squeaks, "so what brings you here? This isn't exactly the most popular restaurant in town."

"I was driving around the area and I figured I might as well get a bite to eat before I head out for my late shift at Brotman Medical Center."

She smiles, "Wow that's great Jason! I'm glad you're getting to pursue your dreams."

"Yeah, it's great. Being a doctor is all I ever wanted to do. What about you?"

She laughs, "Besides working at a shoe store to get the bills paid I don't have a real job. But I'm trying to get into a good singing career. It's really a passion of mine right now and I'm hoping to start writing my own songs, but for now I'm just singing covers of songs and seeing who will listen."

"That's great Madison. I've got to grab a bite to eat...do you want to join me?" He asks.

She smiles, "I'd love to."