In 1995, the Jacobs family embodies the spirit of a close-knit Italian-Jewish household. The parents, Pat and Alan, navigate the troubled waters of their marriage, characterized by Pat's growing indifference towards Alan, who persistently seeks her affection but only receives her cold shoulder in return. Their eldest daughter, Dana, is stuck in a stagnant long-term relationship with her fiancé, Ben, while the younger sister, Ali, is still in high school, more fascinated by raves and getting high than by the prospect of college.
After a night out, Ali inadvertently stumbles upon a set of her father's heartfelt love notes to an enigmatic woman known only as "C." Simultaneously, Dana encounters her ex, Nate, at a party where tension brews as she flirts with both Ben and Nate. Seeking some personal space, Dana decides to take a day away from her obligations with Ben and finds herself in a compromising situation with Nate.
When confronted by their parents about their questionable actions, Ali retreats to the family's country home with her boyfriend, only to find Dana has also sought refuge there. This unexpected reunion leads them to share secrets, with Ali expressing her shocking suspicion about their father's potential infidelity, while Dana, ridden with guilt, admits her own betrayal of Ben.
Determined to uncover the truth about "C," Dana moves back home to aid Ali, but continues her reckless affair with Nate—disregarding her fiancé, Ben. The sisters encounter a dead end in their quest, but at a staged reading of Alan's play, they meet Carla, an actress they suspect to be the mysterious "C." In a moment of irony, Dana is upset by this revelation, but when she relays it to Nate, he dismisses her worries, leading to the end of their affair.
After a heart-to-heart with her father, during which Dana confesses her uncertainty about her life direction, she begins to reconsider her relationship with Ben, realizing the unfair treatment he has endured. On Halloween, Dana meets with Ben to confess her infidelity, resulting in their heartbreaking split. Subsequently, Ali convinces Dana not to engage in a risky drug deal, but their evening takes another turn as they are arrested.
Meanwhile, Pat seeks solace at a bar, where she flirts with another man but ultimately returns home to Alan. In a heated confrontation, Pat reveals her knowledge of Alan's affair with Carla, while Alan counters with memories of Pat's previous rejection of his advances. Their argument is abruptly interrupted by a call from jail, prompting Alan to pick up his daughters. When they return home, they find Pat in disarray, who ultimately confesses her affair to them, prompting a heartfelt embrace.
As events unfold, Dana fervently pursues Ben, pleading for a second chance. Alan decides to move out but promises to remain involved in his daughter's lives. The family's journey culminates at Ali's birthday party, where they come together to celebrate their complicated yet enduring ties.
