Cal Weaver's life, a middle-aged man, takes an unexpected turn when his wife, Emily, confesses that she has had an affair and wants a divorce. Overwhelmed by the situation, Cal dives into a world of singledom that he doesn’t quite understand. In a bar, he meets Jacob, a relentless womanizer who becomes his mentor in the art of seduction. With Jacob's help, Cal begins to reinvent himself, learning to attract women and, consequently, regaining his confidence.
Meanwhile, the story complicates as Emily tries to regain her love life, and her relationship with the entire surrounding environment gets entangled in unexpected ways. David, Cal's son, is in love with his babysitter, who in turn has her own story filled with secrets. Jacob finds himself surprised by his own feelings when he encounters a woman who challenges all his rules.
Through hilarious encounters and touching moments, the complexities of love, family, and second chances are explored. As the lives of these characters intertwine, they discover that love, in all its forms, is often a crazy game of chance, prompting them to question what they are willing to risk to find it. With a brilliant cast and a perfect blend of comedy and romance, the film reminds us that love, although chaotic, is always worth it.