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Helen Harris (Kate Hudson) is living the life she's always dreamed of: her career at a top modelling agency is on the rise; she spends her days at fashion shows and her nights at the city's hottest clubs. But her carefree lifestyle comes to a screeching halt when one phone call changes everything. Helen soon finds herself responsible for her sister's children: fifteen-year-old Audrey (Hayden Panettiere), ten-year-old Henry (Spencer Breslin), and five-year-old Sarah (Abigail Breslin). No one doubts that Helen is the coolest aunt in New York City, but what does this glamor girl know about raising kids? The fun begins as Helen goes through the transformation from super-hip to super-mom, but she quickly finds that dancing at 3a.m. doesn't mix with getting kids to school on time, advice that Helen's older sister, Jenny Portman (Joan Cusack), is only too quick to dish out. Along the way, Helen finds support in the most unusual place, with Dan Parker (John Corbett), the handsome young pastor and principal of the kids' new school, and realizes the choice she has to make is between the life she's always loved and the new loves of her life.

Zoe has always had difficulty letting anyone into her life; she has a habit of pushing people away whenever they get close. Now she wants to have a baby but has no man in her life, so she decides to be artificially inseminated. Shortly after having the procedure, she meets a guy called Stan and feels a spark. When she tells him about her pregnancy she thinks he will bail, but he stays.

Ryden Malby has planned her academic life since she was in high school to get a college scholarship; now she has just graduated in English and in her master plan she expects to get a job as assistant editor in the publishing house Happerman & Browning, in Los Angeles. Her platonic best friend is Adam Davis, who has a crush on her and is frequently close to her. However, her arrogant classmate Jessica Bard gets the position and Ryden is forced to return home in the suburb to live with her family: her optimistic father Walter, who wants to do everything by himself; her careful mother Carmella who administrates the short resources of her family; her eccentric grandmother Maureen; and her weird little brother Hunter, who wants to race in a boxcar derby. Ryden unsuccessfully seeks a job and feels frustrated, but is emotionally supported by Adam. When Walter accidentally runs over the cat of his next-door neighbor David Santiago with Ryden's car, they visit him to give their sympathies. Ryden feels attracted by the handsome Brazilian and has a brief affair with him, forgetting Adam, who decides to move to New York to study at Columbia Law School. Meanwhile Ryden is invited to join Happerman & Browning and discovers that feelings cannot be planned.

Meet the Borgens. William Borgens is an acclaimed author who hasn't written a word since his ex-wife Erica left him 3 years ago for another man. In between spying on Erica and casual romps with his married neighbour Tricia, Bill is dealing with the complexities of raising his teenage children Samantha and Rusty. Samantha is publishing her first novel and is determined to avoid love at all costs - after all she's seen what it has done to her parents. In between hook ups, she meets "nice guy" Lou who will stop at nothing to win her over. Rusty, is an aspiring fantasy writer and Stephen King aficionado, who is on a quest to gain 'life experiences'. He falls for the beautiful, but troubled Kate and gets his first taste of love and a broken heart. A tale of family, love (lost and found), and how endings can make new beginnings. There are no rewrites in life, only second chances.

Struggling with her debilitating obsession with shopping and the sudden collapse of her income source, Rebecca Bloomwood (Isla Fisher) unintentionally lands a job writing for a financial magazine after a drunken letter-mailing mix-up. Ironically writing about the consumer caution of which she has not abided, Rebecca's innovative comparisons and unconventional metaphors for economics grants her critical acclaim, public success, and the admiration of her supportive boss Luke Brandon (Hugh Dancy). But as she draws closer to her ultimate goal of writing for renowned fashion magazine Alette, she questions her true ambitions and must determine if overcoming her "shopaholic" condition will bring her real happiness.

Kassie (Jennifer Aniston) and Wally (Jason Bateman) are best friends. Being unlucky in love, Kassie has decided to have a child using artificial insemination. Wally doesn't like this idea, but he isn't capable of admitting to himself, let alone to Kassie, that he's in love with her. At Kassie's artificial insemination party, Wally gets very drunk and spies the sperm donor's sample in the bathroom. Wally was way too drunk to know what he did that night, and Kassie has moved away because she doesn't feel that New York City is a place to raise a child. Now 7 years later, Kassie has moved back with her son Sebastian. While she is looking to get Roland (the sperm donor) more involved in their lives, Wally can't help but notice the many striking similarities that he and Sebastian share.

Beth is a hard working career woman whose last relationship says that she puts her work above him so he left her. When he tells her he found another career woman and is willing to stick it out with her and is engaged to her, Beth feels that there is no one for her. And when she goes to Rome to attend her sister's impromptu wedding and after meeting the best man, Nick, she's attracted to him but after seeing him with another woman, she gets drunk and goes into the famed Fountain of Love and takes some coins thrown by people looking for love. When she goes back to New York four men start coming onto her. And Nick keeps calling her asking her out. She later learns that what she did--is a no no. It seems legend says that if you take a coin out of the fountain the person who threw it will fall in love with who took the coin. So she has to find a way to break the curse. And she wonders if Nick, whom she likes, is with her cause he wants to or if he is under the spell.

In Manhattan, the lawyer Liv and the school teacher Emma have been best friends since their childhood. They both are proposed to by their boyfriends on the same day and they plan their wedding parties in Plaza Hotel, using the services of the famous Marion St. Claire. However, due to Marion's secretary's mistake, their weddings are scheduled for the same day. None of them agrees to change the date and they become enemies, trying to sabotage the wedding party of the rival.

Melanie Carmichael, an up and rising fashion designer in New York, has gotten almost everything she wished for since she was little. She has a great career and the JFK-like fiancée of New York City. But when he proposes to her, she doesn't forget about her family back down South. More importantly, her husband back there, who refuses to divorce her ever since she sent divorce papers seven years ago. To set matters straight, she decides to go to the south quick and make him sign the papers. When things don't turn out the way she planned them, she realizes that what she had before in the south was far more perfect than the life she had in New York City.

Two things about Jane: she never says no to her friends (she's been a bridesmaid 27 times and selflessly plans friends' weddings), and she's in love with her boss, George, nurturing dreams of a lovely, romantic wedding of her own. She meets Kevin, a cynical writer who finds her attractive, and that same week her flirtatious younger sister Tess comes to town. Jane silently watches George fall for Tess, a manipulative pretender. Worse, Jane may be called upon to plan their wedding. Meanwhile, Kevin tries to get Jane's attention and has an idea that may advance his career. Can Jane uncork her feelings?

Becky (Rachel McAdams) is a hard-working morning TV show producer, or at least she was until she got fired. Desperate to get a job, she finally gets an interview with Jerry (Jeff Goldblum) - who is desperate to hire a producer for the struggling show "Daybreak". Becky accepts the job and it proves to be more difficult than even she might be able to handle. She has to fire the sexist co-host, then try to convince egotistical news reporter, Mike Pomeroy (Harrison Ford), to take the job, and then try and get him to actually do the job, properly. And she has to do this while falling for handsome Adam (Patrick Wilson), and trying to save the show from plummeting ratings. Will Becky be able to hold on to her dream job and her sanity?

Maggie (Hathaway) is an alluring free spirit who won't let anyone - or anything - tie her down. But she meets her match in Jamie (Gyllenhaal), whose relentless and nearly infallible charm serve him well with the ladies and in the cutthroat world of pharmaceutical sales. Maggie and Jamie's evolving relationship takes them both by surprise, as they find themselves under the influence of the ultimate drug: love.

After graduating from Montclair State, New Jersey Girl Annie can't make up her mind about what to do with her life. After saving a little boy from being run over in the park, she is quickly employed as a nanny for a rich Upper East Side couple. Mr X is occupied with his business, Mrs X loves shopping, and neither really likes to spend time with their little boy Grayer. Annie quickly learns that she has more than her hands full taking care of him. Her busy schedule doesn't give her much spare time. Mrs X fired her last nanny because she was dating and that gives Annie problems when Harvard Hottie who lives in the same building asks her out on a date.

Ally is a woman who has many ex-boyfriends who turned out to be losers. Now she believes that she can't find a good guy. But when she runs into one of her exes who is now a 'Prince Charming', she decides to look up all of her exes to see if any of them have changed for the better. When she has trouble locating them, she asks her neighbor Colin, who sleeps with a different women every night and sneaks out the morning after to avoid talking to them, to help her.

Benjamin Barry is an advertising executive competing with two female co-workers for a major campaign for a diamond merchant. He cuts a deal with his competitors that the account is his if he can make a woman of their choice fall in love with him in 10 days. In comes Andie Anderson who, in turn, is writing a story on how to lose a guy in 10 days as a bet with her boss to be allowed to write more substantial stories. With a hidden agenda in each camp, will either party be able to complete their mission?

Rachel is a lawyer. When she was in law school she fell for another student, Dex, who comes from an affluent family, but she was too shy to say anything. When Dex meets her best friend Darcy, who sometimes treats her like dirt, Darcy makes a move on Dex and gets him. Eventually, they get engaged and Darcy asks Rachel to be her Maid of Honor. However, Rachel still has feelings for Dex and still can't say anything. Darcy throws her a birthday party and Dex is there. When she and Dex are alone she blurts out that she had a thing for him in college which surprised him, and after drinking a little they spend the night together. They try to forget the whole thing and agree that it means nothing. Ethan, Rachel's close friend, tells her that she'll spend her entire life regretting that if she does nothing.

For three years, Andrew Paxton has slaved as the assistant to Margaret Tate, hard-driving editor at a New York publisher. When Margaret, a Canadian, faces deportation for an expired visa, she hatches a scheme to marry Andrew - he agrees if she'll promise a promotion. A skeptical INS agent vows to test the couple about each other the next Monday. Andrew had plans to fly home that weekend for his grandma's 90th, so Margaret goes with him - to Sitka, Alaska - where mom, dad, and grams await. Family dynamics take over: tensions between dad and Andrew, an ex-girlfriend, Andrew's dislike of Margaret, and her past color the next few days, with the INS ready to charge Andrew with fraud.

More than a dozen Angelenos navigate Valentine's Day from early morning until midnight. Three couples awake together, but each relationship will sputter; are any worth saving? A grade-school boy wants flowers for his first true love; two high school seniors plan first-time sex at noon; a TV sports reporter gets the assignment to find romance in LA; a star quarterback contemplates his future; two strangers meet on a plane; grandparents, together for years, face a crisis; and, an "I Hate Valentine's Day" dinner beckons the lonely and the lied to. Can Cupid finish his work by midnight?