Set in Baltimore, the story unfolds around the intertwined lives and relationships of several women and men as they navigate the complexities of dating, love, and expectations. Gigi, a young woman perpetually confused by the dating scene, often misinterprets the intentions of her romantic interests, leading to a series of disappointing encounters. Her misadventures and the sage advice from a bar owner she befriends become the central thread that connects the varied experiences of her friends and acquaintances. These experiences range from hopeful first dates to the disillusionment of long-term relationships, highlighting the varied interpretations and misunderstandings of human connections.

Beth is in a committed relationship yet struggles with her partner's reluctance to marry, while Janine faces the crumbling of her marriage over suspected infidelities and the strain of her own trust issues. Concurrently, Anna navigates an affair with a man who is not fully available to her, reflecting the dilemmas of choosing between what is wanted and what is right. Each storyline examines a different facet of romantic relationships, from the raw beginnings to the bittersweet ends, and the often elusive search for love. The narratives interweave to pose and explore the question of how to interpret the actions and words of others in the context of romantic interest, and whether the expectations in love and life align with reality.