In this sharp and heartfelt comedy-drama, directed by Ross Katz, a high-flying tech entrepreneur named Jake (played by Nick Kroll) sees his seemingly perfect life come crashing down after a disastrous product launch and a public meltdown. Forced to reassess everything, Jake swallows his pride and moves back to the suburbs to live with his estranged sister, Justine (Rose Byrne), her husband, Danny (Bobby Cannavale), and their young daughter. With his ego in tatters and no clear path forward, Jake reluctantly takes a job as a nanny for his spirited niece, a humbling assignment that proves far more challenging than any business venture. As he stumbles through the daily chaos of diaper changes and playdates, Jake begins to confront his own arrested development, clashing with Danny’s rigid parenting style and uncovering the quiet fractures beneath his sister’s seemingly perfect family life. Balancing awkward humor with genuine emotional insight, the film explores the messy, often hilarious process of learning to grow up when you’re already supposed to be an adult. With a stellar supporting cast including Joel McHale, Jane Krakowski, Bobby Moynihan, and Mike Birbiglia, Nick Kroll delivers a surprisingly tender performance in this relatable story of failure, family, and the painful necessity of starting over.