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The movie is set in Baltimore, and follows the story of nine people and their varying romantic problems.
Less of an ensemble comedy than a collection of interwoven stories, each of the characters has some degree of relationship with one or two others whether a crush, a date or a full-blown affair.
During a tense home improvement shopping trip, Ben confesses his infidelity to Janine.
She is devastated but rationalizes Ben's behavior, blaming herself for being too cold and domineering and wants to save their marriage; Ben seems less enthused.
At the center is Gigi Phillips (Ginnifer Goodwin), a young woman who repeatedly misinterprets her potential romantic partners' actions.
Gigi (Ginnifer Goodwin) is a single thirty-something woman who repeatedly misreads her dates' mundane actions and comments as indications of their romantic interest, and frets when a guy she likes fails to call her.
Their friendship continues, and Gigi interprets his ongoing helpfulness as a sign he is attracted to her.
Alex rebuffs her advances, claiming he is romantically uninterested and chastises her for ignoring his advice.
The "rule" is that unanswered phone calls and similar behaviors means a man is uninterested, with few exceptions, and that Gigi has been misinterpreting and obsessing over imagined "signs" she is reading.
He is romantically interested in her, but Anna only wants a casual relationship.
Conor misinterprets her playful affection as potential romantic interest.
Following a tepid first date with real estate agent, Connor Barry (Kevin Connolly), Gigi attempts to stage a run-in with him at a local bar he frequents.
She is befriended by bar owner Alex (Justin Long), who enlightens her about strategies men use to brush off women.