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After spending a decade in a failed relationship, successful couples’ therapist Ally (Portman) is turning 40 and is pushed, kicking and screaming, by her best friend back into the hopeless New York dating scene. But Ally finds her life pulled in opposing directions as she falls into a steamy fling with a 20-something Brooklyn hipster just as she begins a promising, more conventional relationship with Alan, a successful 50-something in Manhattan. As a romantic crossroads blossoms into a full-blown identity crisis, Ally juggles to keep these two very different men separate and to make sense of her own conflicting desires before she risks losing them both.