The love which binds mother and daughter - seen through the prism of one mother's life as it crests with optimism, navigates a turning point, and ebbs to its close. Overcome by the power of memory, Ann Lord (Vanessa Redgrave) reveals a long-held secret to her concerned daughters; Constance Haverford (Natasha Richardson), a content wife and mother, and Nina Mars (Toni Collette), a restless single woman. Both are bedside when Ann calls out for the man she loved more than any other. But who is this "Harris", wonder her daughters, and what is he to our mother? While Constance and Nina try to take stock of Ann's life and their own lives, their mother is tended to by a night nurse (Dame Eileen Atkins) as she journeys in her mind back to a summer weekend around fifty years before, when she was Ann Grant (Claire Danes), a young woman who has come from New York City to be maid of honor at the high-society Newport wedding of her dearest friend from college, Lila Wittenborn (Mamie Gummer). The bride-to-be is jittery, and turns to her maid of honor rather than her own mother for support. Ann stays close to her friend, yet is even closer to Lila's irrepressible brother Buddy Wittenborn (Hugh Dancy). Unexpected feelings surge forth once Ann meets wedding guest Harris Arden (Patrick Wilson), a life-long friend and intimate of the Wittenborn family. Ann's love for Harris will change her life, and those of her daughters, forever.

Kate and Charlie have the perfect life planned out: buying a house, marriage, kids, the whole works. Kate's fear of flying keeps her in Canada while Charlie goes to Paris for a medical convention. While there Charlie is smitten by the lovely Juliette. He calls off his wedding to Kate and she nervously boards a plane to get him back. She ends up sitting next to the petty French thief Luc Teyssier. He hides a stolen necklace and smuggled grapevine in her bag to get it through customs. Her bag is stolen, the necklace apparently lost, and Kate and Luc head to Cannes--Luc to find the necklace and Kate to get Charlie back. Along the way, Kate and Luc begin to have feelings for each other, which change the course of their lives.

Emily Jackson lives a fast-paced life. Always on the go, able to talk around the clock, with a sensitive soul she loves playing matchmaker for her friends. It's Emily's gay roommate and frequent companion Peter, who becomes again the subject matchmaking skills when handsome new photographer assistant Paolo arrives at the Vogue offices, where Emily works. She makes it her mission to bring the two men together. Unfortunately for her, she is so busy arranging a love connection between Peter and Paolo that she remains completely blind to the one suitor who longs to provide her with the loving companionship that she so cheerfully arranges for others. And so it does make sense that Peter, a screenwriter in the making, starts telling the story from his own point of view.

Finn is a young graduate student, finishing a master's thesis, and preparing for marriage to her fiance Sam. But thoughts of the end of the free life, and a potential summer fling, intrude. She goes home to her grandmother, where, over the making of her wedding gift by a group of quilting-bee friends, laughter, bickering, love, and advice lead her toward a more open-eyed examination of her course.

A waitress meets personable, attractive Adam and they soon become lovers, then get engaged. Wasting no time, Adam starts an affair with her bookish sister, who knows about the first relationship. Their (none-too-happily) married third sister knows about both these liaisons but is still attracted to Adam. The lad is certainly playing the field, but in their own ways the girls seem to be getting just as much out of the deal as him.

Nora Wilder is freaking out. Everyone around her is either in a relationship, married, or has children. Nora is in her thirties, alone with job she's outgrown and a mother who constantly reminds her of it all. Not to mention her best friend Audrey's "perfect marriage". But after a series of disastrous dates, Nora unexpectedly meets Julien, a quirky Frenchman who opens her eyes to a lot more than love.

In New York City, thirty-three year old Patti Petalson is unhappy with her life. Her passion is literature, she having published one book of short stories ten years ago, but not having written anything since. Instead to earn a living, she sells real estate, a job and for a boss she hates. And although unspoken, she hates her husband, self-absorbed restaurateur Chazz Coleman, who doesn't listen to her and does whatever he wants regardless of her. While out for dinner, Patti and her BFF, schoolteacher Kate Scott, run into Brian Callahan and Michael Murphy, who were once Patti and Kate's respective boyfriends, the four who used to do everything together while they were in college, with both relationships ending twelve years ago as they were graduating. Kate has never forgiven self-described lowbrow Murph, now a successful lawyer despite his lack of academic smarts, for what she believed was a sexual indiscretion, while Murph outwardly just wants the opportunity to apologize. However, there is an unspoken attraction still between Patti and Brian. Brian is also somewhat unhappy with his current life. He is a successful writer of a series of what he considers "pulp fiction" detective novels, but has just written his first serious novel - one he doesn't admit to anyone is semi-autobiographical in that its lead character is a man trying to rise to greatness out of mediocrity - which is being panned by the critics, with his fans refusing to read it. He is dating twenty-five year old record company executive Bernadette, the two of them who live in separate generations and as such don't really understand each other. As Patti, Brian, Kate and Murph reconnect, the questions become whether there is a second life for them as couples, and specifically for Patti and Brian if their reconnection can elevate them into being the writers they truly want to be.

Claudia has lived all her life in a small, seaside, blue-collar town, hanging out with the same group of friends since grade school. Now she's waiting tables in a greasy spoon to help support her mother. After three years together, her live-in boyfriend, Michael, is eager to tie the knot. Their life together is comfortable and Michael loves her. But Claudia has dreams of life beyond her home town and is afraid that if she marries now, she'll never realize them. Claudia's sister Kelly lives with her mother and struggles with good humor to care for her fatherless baby. Their mother hasn't left the house since Claudia's dad walked out on the family six months ago. No one understands why Claudia sympathizes with her renegade father. Like him, she has a wild, restless streak and longs for more. But she can't quite put her finger on what it is she wants. So when her old flame, Charlie, returns from out west, she begins to wonder... maybe he's the answer.

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