The movie start off with Rachel (Ginnifer Goodwin) outside a club looking apprehensive and resigned. She pulls open a curtain and sees Darcy (Kate Hudson) and her friends beneath a Happy 30th Bday sign. Darcy goes up to Rachel and tells her that she knows she hates surprises but, she couldn’t resist and wasn’t Rachel surprised? Rachel nods weakly as Darcy then screams and command the center of attention by announcing that it was such a great idea that she had and how it was all because of her (this sets it up for the rest of the night, where Darcy is the center of attention even though it’s Rachel’s B-day Celebration.
Darcy goes up to the stage set up with two screens showing pictures of Darcy and Rachel (with Darcy being prominent) and explains how she and Rachel have grown up together and how they were best friends. She also credits Rachel for introducing her to her fiancé Dex (Colin Egglesfield) and how glad she is for not turning 30 and alone. Rachel flashes back to the night that she and Dex had a pseudo date (they were both too shy to take the next step), and Darcy shows up, and dares Dex to ask Rachel out on a real date. Rachel denies having feelings for Dex because she was sure that he wouldn’t be into her and so Darcy dares him to ask her out. He checks with Rachel to see if it’s OK with her and she plays it off like she’s OK with it.
Rachel’s friend Ethan (John Kransinki) makes snide remarks about Darcy and there’s a subplot with him and another girlfriend of Darcy’s who chases him. He acts as Rachel’s conscience throughout the movie she is constantly sharing her feelings and tells him everything that is going on.
Darcy leaves drunk, and Rachel and Ethan are the last to leave, Ethan’s hailing a cab when Dex shows up in the cab that Ethan hailed and said that Darcy has lost her purse. Rachel offers to help find the $2k purse and Ethan takes off in the cab. After Dex and she find Darcy’s purse, Dex invites her to have a drink. They are at a bar when Rachel notices that another girl is looking daggers at her because Dex didn’t respond to her flirting. She remarks that he doesn’t know how women see him, and they start talking about their time in law school. Rachel lets slip that she had a major crush on him, and he responded by saying basically the same. Things get awkward and then they leave by taxi, where Dex makes a move on Rachel, and they kiss in the cab.
Cue the next morning, where they wake up in bed together, and the phone is ringing off the hook because Darcy is frantically trying to call them both. Dex has 14 missed messages, and they hurriedly dress, and Dex runs off promising to take some time to talk with Rachel in private. There are scenes where Darcy shows how shallow and selfish she is and they all rent a place in the Hamptons …cheating takes place between Rachel and Dex. She finally asks him to give Darcy up, but he is not willing to risk his family’s censure to do so. She ends the affair and makes a trip to London to see Ethan.
In the end, Ethan moves to London for a job and to get away from the drama. Rachel learns that Ethan loves her and that she still loves Dex, even though he wouldn’t leave Darcy. When she returns, Dex is at her apartment telling her that he canceled the wedding and is in love with her. Darcy shows up and Dex hides. She then tells Rachel that she’s the one who ended the engagement and is pregnant with Marcus’s (Steve Howey) baby, who she was trying to hook Rachel up with. As she leaves, she sees Dex’s jacket and demands to know where he is. He comes out and tells her that he heard everything. She accuses them of lying and cheating on her and tells Rachel she never wants to see or talk to the both of them again.
A few months later, Rachel is seen walking with Dex’s dry cleaning and sees Darcy on the street looking pregnant. Rachel smiles and says hi, Darcy points out that she bought the shirt that Rachel’s carrying for Dex. Rachel asks if she’s well wishes her the best. Darcy walks away but turns back and gives Rachel a genuine smile and says that, yes, she’s really happy. Rachel then continues to walk, and Dex takes the dry cleaning, and they walk hand in hand down the street.
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