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Nick and Charlie are inseparable, but with Nick preparing to leave for university and Charlie finding new independence at school, the reality of a long-distance relationship begins to weigh on them. Doubts take hold, and their relationship faces its biggest challenge yet. Meanwhile, their friends are also navigating the ups and downs of love and friendship, confronting the bittersweet challenges of growing up and moving on. Can first loves really last forever?
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.