Jessica Stein is a successful yet neurotic journalist living in New York City, disillusioned with her dating experiences. She's spurred into trying something new when she stumbles upon a personal ad from Helen Cooper, a woman also struggling to find meaningful relationships with men. Despite initial hesitation and awkwardness, Jessica decides to take a chance and meets Helen for a date. To her surprise, they share a deep connection and find themselves increasingly intrigued by the possibilities of a relationship that defies their previous romantic norms.

As Jessica and Helen navigate their evolving bond, they face various challenges, not only adjusting to their new romantic dynamics but also dealing with societal expectations and their own insecurities. While Jessica grapples with her identity and the reactions of her friends and family, Helen must reconcile her newfound feelings with her more fluid approach to life and love. Their journey explores themes of self-discovery, acceptance, and the complexities of modern relationships, leading them down a path neither had anticipated, full of emotional growth and unexpected turns.