Kate Welles (Famke Janssen) is a beautiful and talented magazine writer who turns to her own life for inspiration when she is given an impossible assignment. Within twenty-four hours, Kate must write a single woman's guide to love and sex. A stranger to both since her break-up with Adam Levy (Jon Favreau), Kate conducts her research by recalling her many calamitous relationships with men, beginning with her first kiss and her first betrayal on the sixth-grade playground. More heartbreaks follow over the years, with married men, Mama's boys, and a multitude of disappointing bachelors. But the man who seems to have had the most impact on her life is Adam, an artist who does not look -- or behave -- like a typical Prince Charming.
Outspoken, outrageous, and a little out of shape, Adam enjoys the realities of their impulsive love affair and encourages Kate to do the same. He loves her big feet. She loves his oversized head. They share jokes, kittens, good times and bad days. Their relationship progresses quickly. Funny, intense, comfortable and candid, the lovers settle into a cozy domestic routine. Kate's unexpected announcement that she is pregnant catapults their romance to a new level. Adam is eager to become a father and Kate nervously anticipates motherhood and the commitment that goes with it.
An untimely miscarriage ends their fantasy of becoming a family. Grief turns into boredom and indifference, prompting Adam to decide that he is ready to move on. He knows that Kate has had more sexual experience than he has and feels that it is time to catch up -- to sample the inviting variety of single women he sees every day.
Kate is devastated. Even though she is less enthusiastic about Adam than she was at the beginning of their romance, she is shocked by his decision to leave. She fights back by dating other men. Determined to make Adam regret his decision, Kate takes every opportunity to flaunt her sexual independence. But the dating scene is still hell.
Ironically, the moment Kate settles into a new affair with a handsome and charismatic actor, Adam decides that he has made a terrible mistake. He wants to come back into her life and he is ready to make a real commitment. Kate resists at first, finally coming to a surprising conclusion. Love and sex, when combined with friendship, add up to the perfect relationship.
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