Cal Weaver's seemingly perfect life unravels when his wife Emily confesses she's been unfaithful and wants a divorce. Devastated, Cal moves out and begins frequenting a bar, where he meets Jacob Palmer, a suave womanizer. Jacob takes Cal under his wing, teaching him the art of picking up women and boosting his confidence. Despite his new lifestyle and a series of flings, Cal struggles to move on from Emily and adapt to his new reality.

Simultaneously, Jacob finds himself drawn to Hannah, a bright and determined law student who unexpectedly captures his heart and makes him reconsider his shallow ways. The interplay of all characters—including Cal and Emily’s children, who have their own views on love—leads to a series of comedic and heartfelt situations that explore the complexities of relationships, self-discovery, and the enduring nature of love. As secrets unfold and connections deepen, everyone involved reevaluates what they want from their lives and their loves.