New York City. The first night of fall. Three women seek love in three very different ways.
Sasha (21) is an impulsive young woman consumed by a volatile relationship with a passionate writer, Gavin. After yet another fight, Gavin refuses to play along with their evening plans. Sasha takes off with her best friend instead.
Jessie (33) is a successful ad exec searching the Internet for her perfect match. Increasingly desperate, she agrees to meet Frank, an average guy from Brooklyn, but she abruptly ends the date, regretting the whole idea. She tries to salvage her night and looks for better plans.
Lauren (42) is a sensible woman in an ideal Manhattan marriage: Upper West Side apartment, modest wealth, and a single child. And yet, she feels something is missing. In an attempt to re-ignite their spark, she and her husband Greg decide to attend a swingers party.
As the night goes on, Sasha meets-up with an ex-boyfriend, tempting fate and her commitment. Gavin reaches out to Sasha and implies he is considering suicide, then abruptly ends their phone call. Racing to find him, Sasha is forced to question the meaning of relationships and confront the bittersweet reality of young love.
Frank finds Jessie outside trying, in vain, to make new plans. He suggests they just hang out as friends until she hears back. As the night wears on, Jessie ends up having fun despite herself, and ultimately she chooses to stay with Frank. Late night turns into early morning and she realizes that making a choice between her expectations of the perfect relationship and what she feels in her heart isnt so simple.
At the swingers party, Lauren and Greg find themselves reluctant to join in and begin to second-guess their decision. Greg is suddenly propositioned and they are suddenly drawn into a world of sex without boundaries. Soon they are participating beyond the point of no return. Despite every preparation, the night forever changes how they view each other, and more importantly, how they view themselves.