Disclaimer: I don't own the characters from Once and Again. I'm just a fan writing a fanfic. Please don't sue me.

Rating: PG-R (Just to be Safe)

Storyline: This is somewhat based on the movie, Kissing Jessica Stein. But I added a little of my own touch on it. Hope you enjoy it!

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Part I: Brief Introductions

Along the busy streets of New York we would find Jessica, Jessie, Sammler walking by. Like all the other good citizens of NY, she wakes up early in the morning from her Chambers St. home to grab a cup of coffee from Starbucks. After which she would cross City Hall Park to get to her workplace: NYU Downtown Hospital. As she reaches the hospital two loving guards would check her bag and her backpack as part of a routine check since the dawn of 9-11. She would pass by Tad's office, the director of the hospital, Jessie's ex-boyfriend. She would wave like she always does and never look back. She did have trouble finding the great guy after she broke up with Tad. She didn't really want him to see she was at times lonely. Grace, Jessie's dearest friend, a mother of two, and wife to Jessie's brother Eli would greet her as she arrives at her office. More often than not, flowers were not the decorations for the lovely Ms. Sammler's office; they were post-its. Her mother Karen would call Jessie every one in a while convincing her to date a few men she knows. At 30, Jessie wasn't getting any younger. Her mother was in so much haste for her to settle down. And so was the rest of her friends and family. Once or even twice a week, Grace would set-up Jessie with a common friend. In the end Jessie would find them utterly boring, and useless. Not that they really were. It's just how she felt when she talks to them. Like nothing will ever give her the flip-flops and the fireworks. Anything that comes out of the mouths of every man she dated seemed to be refutable. Like nothing was real. She goes back home in a cold bed at times wondering where the person who supposed to be beside her is.

Love is a puzzle for Jessie. Sometimes she wished she didn't really bother trying to solve it anymore.

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In a posh condominium not so far away lived Katie Singer, a well renowned artist. So renowned, every Art Gallery in New York wanted a piece of her. From her Manhattan condo she would walk along Central Park to gaze into the beauty of nature. Though her works are somewhat liberal and simply modern, Katie wanted her works to reflect the person the she is; sophistically and totally, gay. Nobody really cared if Katie Singer was gay. It was the sign of the times. She proved that women can survive without men, as long as there are women around. Socially a player by her own right, Katie Singer, at 31, could make women and even men fall in love with her if she chooses to. She just had more preference with the female specie. Sarah Grasso, her current amour, the luscious model from Ford was just the tip of the ice berg. Katie had a whole list of girls that would make up a card catalog in a university library. As she walks back to her condo Katie would sit back alone if she didn't bump into a female who wouldn't want to spend time with her. At these times she would drink her wine, looking at the starry Manhattan skyline. Of all the love and the women in her life. She still wasn't happy. She would start to draw or paint like the world faded, like a lifeless routine that she could never get away from.

Love is easy for Katie Singer. Pretty much a game she had perfectly mastered. Knowing that, happiness never really mattered.