Rachel White (Ginnifer Goodwin) is a single, talented attorney working in a New York law firm. After too many drinks on her 30th birthday, Rachel grabs a cab with Dex (Colin Egglesfield) and playfully reveals she has had a crush on him since law school. The problem is, Dex is also her best friend Darcy's (Kate Hudson) fiancé. They wake up in bed together the next morning to Darcy calling both of their phones. Dex sneaks out and they do not have time to speak about what happened between them. What Rachel thinks is a one night stand, is actually the beginning of an emotional roller coaster once Dex tells Rachel he is in love with her.



Ethan (John Krasinski) has been friends with Darcy and Rachel since childhood. He is the only one who knows what has happened between Rachel & Dex, which he has vowed to keep secret.



Meanwhile, Dex’s mother (Jill Eikenberry) has been suffering from depression for some time and Dex and Darcy’s wedding is the only thing keeping her sane and happy.



When Dex skips out on 4 July weekend in the Hamptons to stay in the City and spend time with Rachel, they run into his parents. His father suspects something is going on between the two of them and he tells Dex to end it as soon as possible. Considering his mother and father’s feelings, Dex gives Rachel the cold shoulder and leaves her to go back to Darcy (who has been partying the Hamptons all weekend with Dex’s best friend, Marcus).



As the wedding nears, Dex and Rachel are speaking less and less. Ethan moves to London for work after he becomes angry at Rachel for not standing up for herself & her feelings.



Rachel flies to London to visit Ethan who then reveals that he has been in love with her the entire time and just wants to see her happy. Rachel returns to New York to find Dex sitting on her door step. He reveals he ended things with Darcy and called off the wedding. Rachel is ecstatic until Darcy ends up at her door begging to come in to talk. Dex hides and Darcy enters her apartment. She tells Rachel that she ended things with Dex and has been cheating on him with his best friend Marcus. She is also pregnant with Marcus’ child and they are very happy. Rachel gives her her blessing and Darcy proceeds to leave but only to return and ask what Dex’s jacket is doing in her apartment. Dex then comes out and Darcy figures out Rachel is the other woman. She becomes infuriated and storms out of the apartment.



Two months later, Rachel & Darcy run in to each other on the street, they have not spoken since the incident and Darcy says she is extremely happy. Rachel is happy for her. As they leave, Rachel walks around the corner to Dex sitting on a bench. They walk down the street hand in hand.