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The plot chronicles the romantic misadventures of nine individuals in their twenties and thirties. Set in Baltimore, the common thread of the story is that one person in each relationship is more enamored with the other person than vice versa. At the core of these multiple stories is Gigi (Ginnifer Goodwin), a young woman who repeatedly misinterprets the signs that men give her about their level of interest in her. After a rejection from Conor (Kevin Connolly), Gigi begins getting dating advice from the romantic and promiscuous Alex (Justin Long), the manager of a bar and Conor’s best friend.
Gigi’s co-worker Janine (Jennifer Connelly) is having difficulties in her marriage. Her husband, Ben (Bradley Cooper), begins cheating on her with Anna (Scarlett Johansson), a yoga instructor and aspiring singer. Anna, in turn, is dating Conor, but isn’t as interested in him as he is in her. Anna receives romantic advice from Mary (Drew Barrymore), a newspaper editor who also helps Conor promote his real-estate business. Gigi’s other co-worker, Beth (Jennifer Aniston), is living with her boyfriend Neil (Ben Affleck), who also happens to be friends with Ben, and who she has been dating for seven years. Beth is upset that Neil refuses to marry her which prompts a breakup.
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