Five couples' intertwined lives are turned upside down by the challenges of impending parenthood. Over the moon about starting a family, TV fitness guru Jules and dance show star Evan find that their high-octane celebrity lives don't stand a chance against the surprise demands of pregnancy. Baby-crazy author and advocate Wendy gets a taste of her own militant mommy advice when pregnancy hormones ravage her body; while Wendy's husband, Gary, struggles not to be outdone by his competitive alpha-Dad, who's expecting twins with his much younger trophy wife, Skyler. Photographer Holly is prepared to travel the globe to adopt a child, but her husband Alex isn't so sure, and tries to quiet his panic by attending a "dudes" support group, where new fathers get to tell it like it really is. And rival food truck chefs Rosie and Marco's surprise hook-up results in an unexpected quandary: what to do when your first child comes before your first date?

Kathryn Merteuil and Sebastian Valmont are seductive, manipulative step-siblings who get what they want when they want it. Kathryn makes a bet with Sebastian: Sebastian must bed Annette, daughter of the headmaster at their school, before the end of summer break. Annette has stated that she would wait until love and marriage to sleep with a man. If Kathryn wins, she gets Sebastian's vintage 1959 Jaguar Roadster. If Sebastian wins, he gets Kathryn, the only girl he knows he'll never have. Also in play is Cecile, a naïve girl whose mother had enlisted Kathryn to help her fit in at her new school. However, Kathryn (with Sebastian's help) plans to ruin Cecile's reputation as revenge on Kat's ex-boyfriend, who left her for Cecile.

Charming, relatively poor, somewhat goofy Tom falls in love with haughty snob tycoon McNerney's spoiled daughter Sarah, who was destined for a more socialite match, such as slick Peter Prentiss. They still get married and fly to Europe for a romantic honeymoon Tom can't afford. Their love gets tested dangerously by misfortune of technical and other kinds all the way. Worse, Peter catches up with them on a mission to 'make Sarah see sense' just when the newlyweds are furious at each other.

Novalee Nation (Natalie Portman) is a pregnant seventeen-year-old from Tennessee heading to California with her boyfriend Willie Jack Pickens (Dylan Bruno), but is abandoned by him at a Walmart in Sequoyah, Oklahoma. Novalee has no job, no skills, and only five dollars and fifty-five cents in her pocket, so she secretly lives in the Walmart until her daughter Americus (Mackenzie Fitzgerald) is born six weeks later. Novalee decides to raise her daughter and rebuild her life in Sequoyah, Oklahoma, with the help of eccentric but kind strangers. Based on the best-selling novel by Billie Letts.

Chris Brander has always been friends with Jamie Palamino, but now decides it is time to take his relationship to the next step. The problem is that Jamie still wants to be 'Just Friends'. When he runs away and moves to L.A., he becomes an attractive music manager, whom everyone wants. When his jet catches fire and is forced to land, when flying to Paris with his newest singing sensation, Samantha James, he ends up back home. To his surprise, he encounters Jamie again, and sets out to be more than 'Just Friends' this time.

In a nursing home, resident Duke reads a romance story to an old woman who has senile dementia with memory loss. In the late 1930s, wealthy seventeen year-old Allie Hamilton is spending summer vacation in Seabrook. Local worker Noah Calhoun meets Allie at a carnival and they soon fall in love with each other. One day, Noah brings Allie to an ancient house that he dreams of buying and restoring and they attempt to make love but get interrupted by their friend. Allie's parents do not approve of their romance since Noah belongs to another social class, and they move to New York with her. Noah writes 365 letters (A Year) to Allie, but her mother Anne Hamilton does not deliver them to her daughter. Three years later, the United States joins the World War II and Noah and his best friend Fin enlist in the army, and Allie works as an army nurse. She meets injured soldier Lon Hammond in the hospital. After the war, they meet each other again going on dates and then, Lon, who is wealthy and handsome, proposes. Meanwhile Noah buys and restores the old house and many people want to buy it. When Allie accidentally sees the photo of Noah and his house in a newspaper, she feels divided between her first love and her commitment with Lon. Meanwhile Duke stops reading to the old lady since his children are visiting him in the nursing home.

1972. Vada Sultenfuss (played by Anna Chlumsky) is an intelligent, bubbly, hypochondriacal 11-year old girl. Her father, Harry (Dan Aykroyd), is a mortician and a widower. Her best friend is Thomas J Sennett (Macaulay Culkin). Then her father hires a new receptionist, Shelly (Jamie Lee Curtis), and life will never be the same again.

After years of looking for Mr. Right, Charlotte 'Charlie' Cantilini finally finds the man of her dreams, Kevin Fields, only to discover that his mother, Viola, is the woman of her nightmares. A recently fired news anchor who is afraid she will lose her son the way she has just lost her career, Viola determines to scare off her son's new fiancé by becoming the world's worst mother-in-law. While Viola's long-time assistant Ruby does her best to help Viola execute her crazy schemes, Charlie decides to fight back and the gloves come off as the two women battle it out to see just who is the alpha-female.

In this modern-day romantic tale, Penelope is about a young girl's inspiring journey, a mysterious family secret, and the power of love. With all odds against her, in order for Penelope to break the family curse, she must find true love with "one of her own kind". Penelope Wilhern, born to wealthy socialites, is afflicted by the Wilhern spell that can only be broken when she finds love. Hidden away in her family's estate, the lonely girl meets a string of suitors in her parents' futile attempt to break the curse. Each eligible bachelor is enamored with Penelope and her sizable dowry; until her curse is revealed. Lemon, a mischievous and eager tabloid reporter, wants a photograph of the mysterious Penelope and hires Max to pose as a prospective suitor to get the shot. The handsome down-on-his luck gambler finds himself falling for Penelope, but cannot bring himself to give her what she wants. Fed up by this latest betrayal and determined to live life on her own terms, Penelope breaks free from her family and ventures into the world alone. She finds adventure and Annie, her first friend, and goes on a journey to discover the world and who she wants to be.

Samantha's life is going downhill fast. The sixteen-year-old has a crush on the most popular boy in school, and the geekiest boy in school has a crush on her. Her sister's getting married, and with all the excitement the rest of her family forgets her birthday! Add all this to a pair of horrendously embarrassing grandparents, a foreign exchange student named Long Duk Dong, and we have the makings of a hilarious journey into young womanhood.

Undercover F.B.I. Agent Gracie Hart shows no signs of having any femininity in her demeanor or appearance. Generally a bright and capable Agent, she is in trouble at work when she makes an error in judgment in a case which results in a near disaster. As such, one of her by-the-books colleagues, Eric Matthews, who has never shown any inclination of thinking outside the box, is assigned to lead the high profile case of a terrorist coined The Citizen instead of her, while she is facing possible disciplinary action. Gracie pieces together the evidence to determine that The Citizen's next target will be the Miss United States beauty pageant. The pageant represents everything that Gracie abhors. Despite Gracie's mannish demeanor, Eric, with no other undercover female Agent remotely fitting the demographic, assigns her to go undercover as a pageant contestant to see if she can flush out The Citizen, who is perhaps one of the other contestants. Although the pageant administration, led by former winner Cathy Morningside and long time host Stan Fields, provide the F.B.I. with access to the pageant, Cathy in particular is less than thrilled to have a non-credible Gracie posing as a contestant, which she feels will ruin the pageant. The F.B.I. enlist the assistance of former pageant contestant coach Victor Melling, who is facing his own disgrace associated with the pageant, to do the nearly impossible task of transforming Gracie, not only into a woman, but a credible beauty pageant contestant. As Gracie proceeds in the transformation, she gets to know the other contestants, not only as potential criminals, but also as real people. She also discovers that another sinister element is present at the pageant. She will do whatever it takes to quash that element and protect her new friends, namely the other innocent contestants. But now displaying some femininity, Gracie begins to have more womanly feelings, and in turn, attracts the attention of men, one in particular about whom she is happy.

2000 comedy film directed by Donald Petrie

At 35, Tripp has an interesting job, a hip car, a passion for sailing, and a great house - trouble is, he lives with his parents. They want him out, so they hire Paula, an "interventionist," who has a formula in these cases: chance encounter, get him to ask her out, involve him in a trauma, meet his friends and get their nod, delay sex, have him teach her something, then launch him. It's worked up to now, but this gets complicated when Tripp thinks she's getting too serious and one of his pals is attracted to Paula's deadpan, semi-alcoholic roommate, who's plagued by a mockingbird. Too many secrets may scrub the launch, and what if Paula really likes him? Who can intervene then?

Twelve year old Marcus Brewer lives with his chronically depressed single mother, Fiona Brewer. Both Fiona and Marcus beat to their own respective drummers. Marcus will do whatever he can to make his depressed mother happy, even if it causes himself grief. As such, he realizes that he is perceived as different than most kids, as even the self-professed weird kids don't want to hang out with him as he is the target of bullying. Part of the taunts against him are the fact that he sings and speaks to himself without even realizing that he is doing it. Meanwhile, thirty-eight year old Will Freeman is a slacker who has lived comfortably off the royalties of a song written by his deceased father, and as such has never had to work a day in his life. He is a solitary man who places himself as the first and only priority in life. He comes across the idea that dating single moms meets his selfish carnal needs. It is in this capacity that Will meets Marcus, as one of Will's single mother conquests, Suzie, is friends with the Brewers. Trying to escape his life but wanting Will to date Fiona, Marcus infiltrates Will's life, much to Will's chagrin. Will slowly begins to realize that Marcus is more than just a nuisance, but rather someone who needs some guidance navigating through the trials of adolescence and the trials of dealing with a suicidal mother, and perhaps he can be a small part of providing that direction. Conversely, Marcus may be able to show Will the path to becoming a real adult.

2002 film directed by Chris Weitz and Paul Weitz

Sparks fly and cultures collide in this romantic comedy about a casual night of passion that turns into the love of a lifetime. Alex Whitman is a New Yorker sent to Las Vegas to oversee a construction project. There he meets Isabel Fuentes, and some serious chemistry brings them together for one night. But Alex doesn't see Isabel again until three months later, when he learns she is pregnant. On a whim and prayer, he proposes. However, there's more to marriage than a Vegas chapel and an Elvis impersonator, as Alex and Isabel soon learn.

Jonathan Trager and Sara Thomas met while shopping for gloves in New York. Though buying for their respective lovers, the magic was right and a night of Christmas shopping turned into romance. Jon wanted to explore things further but Sara wasn't sure their love was meant to be. They decided to test fate by splitting up and seeing if destiny brought them back together... Many years later, having lost each other that night, both are engaged to be married. Still, neither can shake the need to give fate one last chance to reunite them. Jon enlists the help of his best man to track down the girl he can't forget starting at the store where they met. Sara asks her new age musician fiance for a break before the wedding and, with her best friend in tow, flies from California to New York hoping destiny will bring her soulmate back. Near-misses and classic Shakespearean confusion bring the two close to meeting a number of times but fate will have the final word on whether it was meant to be.

In Boulder, Colorado, Grady, who comes from an old money family but who has struck out on his own as a half owner of a fly fishing business, has just unexpectedly passed. Beyond her extreme grief, Gray, his loving fiancée, the two who were to be married in only a couple of days, is placed in a difficult position as they had no assets in their joint names, and without a will she is legally left with nothing of his except the engagement ring, one half of a family heirloom set along with the wedding ring she was about to receive, the engagement ring which his mother, Ellen, would like back. Gray cannot even afford to live in the rental house she and Grady were to live in, and as such, she, at least in the short term, moves into Grady's old room with his two roommates and best friends, Dennis, Grady's quiet, straight-laced business partner, and somewhat clueless Sam, a copywriter of sorts with Celestial Seasonings Tea. The fourth in that buddy friendship is Fritz, a Los Angeles based director of commercials, he who came in for the funeral and who is staying with Dennis, Sam and now Gray for as long as he is in town. Gray has never much liked seemingly self-absorbed Fritz, his current presence which only strengthens that notion as he displays no sense of anything about Grady, let alone grief. In the process of dealing with his estate, Gray discovers some hidden aspects of what was Grady's recent life, both of a financial nature and an associated personal nature. She turns in part to Grady's friends for answers and support, and while Dennis is the one who wishes she turned to in being secretly in love with her, Gray ends up bonding unexpectedly with Fritz as this information answers a lot of questions she had about his and Grady's friendship. Things within this grouping get even more complicated with the arrival into town from Los Angeles of a woman named Maureen and her preschool aged son Mattie, who are somewhat in the center of that hidden issue concerning Grady.

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