Jack Kelly, Connor Brody](/actor/bobby-cannavale), and Mike Richards are longtime friends and colleagues, now facing the challenges of life in their 50s. As they navigate the expectations of today's world, Connor encounters tension with his wife, Cara, when he urges their son Colin (Dominic Grey Gonzalez) to apologize for his misbehavior. The trio decides to offload their company, Trifecta, to a group of millennials, but to their dismay, they find themselves as the only older employees retained when their new boss, Aspen, chooses to fire everyone over 35 in a bid to modernize the company, making it both gender- and carbon-neutral.
Jack experiences a public reprimand from the director of his son Nate’s preschool for being late, which prompts an outburst of colorful language from him. His wife, Leah, insists he apologize to maintain favorable standing for Nate's admission to a private kindergarten, highlighting Jack's ongoing struggles with anger management. When they go to apologize together, he encounters several parents who detail their grievances, and he attempts to mend the situation by apologizing profusely. Leah emphasizes that Jack must maintain composure for three months to secure that recommendation for Nate.
Meanwhile, Mike, who is newly single and the father of two adult sons, is faced with an unexpected revelation from his young girlfriend, Britney: she's pregnant, despite his having undergone a vasectomy. During a night out at a bar, the trio provides comic relief as Jack and Connor encourage Mike to see the silver lining in his predicament.
As Jack is tasked with organizing a school fundraiser, he and Connor feel increasingly sidelined by the millennial employees. Their adventure takes a turn when they are sent to locate Ed Cameron, a man who has chosen to disconnect from modern life since the 80s. Along for the ride is Travis, a younger employee whose critiques of their camaraderie lead to a confrontation with Mike. Unfortunately, their troubles compound when their misadventures with a rental car lead to them being fired: a hidden camera catches their off-color jokes, and even Travis faces consequences for his unfiltered behavior, revealing the challenges of generational differences.
In a twist of fate, Leah confronts Cara when her son Colin hits her pregnant belly, escalating into a conflict that adds strain to their already fragile relationships. After getting fired from Trifecta, Mike distances himself from Jack, and with Connor unable to reach out due to his wife’s anger, Jack becomes consumed by his responsibilities for the fundraiser. Unfortunately, another outburst results in Leah kicking him out, prompting him to cross paths with Mike at a late-night diner where they eventually reconcile. They invite Connor on a bachelor party road trip that leads to a chance encounter with Aspen, who has also been dismissed from her position.
The night culminates at a strip club, where Jack receives an urgent call that Leah is going into labor. With their luck running low and under the influence, they scramble for an Uber that moves frustratingly slowly, ultimately resorting to small electric scooters to reach the hospital. Although Jack misses the birth, he mends his relationship with Leah and commits to therapy, marking a significant turning point in his life. In the end, the family opts for public school for Nate, Jack learns to manage his temper, Mike proposes to Britney with deeper intent, and Connor manages to get Cara to loosen up a bit.
