The movie starts out with a scene capturing women walking down the city streets of New York, zooming in on their shoes. (Warning: there are NO males in this movie. All the major and minor characters are females).
We meet Mary Haines (Meg Ryan), who is working in her yard and talking on the phone with her friend, Sylvie Fowler (Annette Benning), who is the editor-in-chief for a fashion magazine. Mary tells Sylvie not to be late for the lunch event taking place at her home. After their conversation, Sylvie goes to Saks Fifth to get a manicure. She meets manicurist Tanya, who starts gossiping about a perfume saleswoman named Crystal Allen (Eva Mendes) having an affair with Stephen Haines, Mary’s husband. Sylvie stops by Edie Cohen’s (Debar Messing) house to carpool together to Mary’s. We see that Edie’s house is a mess because she has 3 daughters and she is an artist. At the lunch event, we meet the fourth woman of the gang, Alex Fisher (Jada Pinkett-Smith), who is a lesbian writer. Edie announces to the girl that she is pregnant again and proceeds to go to the bathroom. Sylvie goes after Edie and tells her about what she heard about Mary’s husband from Saks. Edie is shocked and they agree not to tell Mary yet.
Mary also finds out about Stephen’s affair when she meets Tanya at Saks. Depressed (her father also fired her), Mary meets up with her mother to her how to deal with Stephen’s infidelity. Mary’s mother, Catherine confesses to Mary that her husband also cheated on her before. Catherine suggested that Mary and Mary’s daughter, Molly, take a vacation with her to forget about everything and make Stephen miss Mary. Sylvie and Edie eventually tell Alex about Stephen’s affair and they all realize that Mary already found out about it when they went to take Mary to the airport for her vacation. Sylvie, Edie, and Alex confront Crystal Allen about her affair with Stephen and tell her to stop, which Crystal Allen just shrugs off.
Stephen misses Mary and starts treating her nicely when she returns. However, Mary runs into Crystal Allen when she goes to a lingerie store. She confronts Crystal in hopes that Crystal will stop seeing Stephen once she sees the wife in flesh and blood. Crystal completely disregards Mary and continues seeing Stephen.
Mary and Stephen have a huge fight and Mary decides to kick him out and get a divorce. Molly, Mary’s daughter, is pretty upset about all this. Sylvie is threatened by a tabloid writer to confirm Mary and Stephen’s divorce or she might lose her job. Feeling betrayed by Sylvie, Mary checks in to a yoga nature camp which helps divorcees cope. Mary meets a woman at the camp and is inspired to change her life. First she gets a hair cut (her hair is straightened). Next, she pursues her dream of designing her own clothing line. Meanwhile, Molly starts sharing her troubles with her self-image with Sylvie since Mary never seems to be there for her.
Mary first confronts Sylvie about trying to be Molly’s mother but the two soon make up. Sylvie quits her job because she is no longer being herself and able to publish what she believes in. with the help of Tanya the manicurist, they start a gossip that Stephen is back together with Mary, which makes Crystal Allen very angry.
Mary’s big night finally arrives: a fashion show for her new line. Her three best friends and mother are there to support her. Molly even thinks her mom is “cool”. The show turns out to be a success, but Mary rejects Saks offer to produce her clothing, thinking it would be too much work for her. All is merry when Edie announces that her water broke. Mary, Sylvie, and Alex rush Edie to the hospital. Under Edie’s guidance about her own experience cheating on her husband, Mary and Stephen talk about giving it another shot on the phone. Edie has very crazy screams and contractions and finally gives birth to a boy
For the closing credits of the film, we see that Sylvie now publishes her own magazine. Alex finally publishes her second book. Mary is carving pumpkins with Molly. We see a tabloid magazine proclaiming that Crystal Allen is now a lesbian, shown holding hands with a super model (Alex’s former beau).
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