Greenberg

As Florence Marr (Greta Gerwig) strolls through the sun-kissed streets, the Greenberg family dog, Mahler, trotting faithfully by her side, she embarks on a routine that will soon take an unexpected turn. Her errand run includes picking up Phillip Greenberg's dry cleaning and stopping by his house to deliver it, where the entire family is in the midst of preparing for their impending trip to Vietnam. Phillip (Chris Messina) fills Florence in on the details of their travel plans, including the fact that his brother, Roger, will be staying behind to look after the property while they're away. He asks Florence to extend a helping hand if Roger needs any assistance, revealing that this particular individual has recently been released from a hospital following a nervous breakdown. Carol (Susan Traylor) confides in Florence about Roger's struggles, implying that his carpentry skills will be put to the test as he takes on a project to build Mahler a doghouse.

As Roger (Ben Stiller) arrives at the Greenberg residence, he reaches out to Florence with a query about the poolside commotion. Florence enlightens him on the fact that these are merely their neighborly friends, permitted to use the pool. Her visit to the house is prompted by her need to collect her paycheck and tend to Mahler's needs. This brief encounter with Roger sets the tone for an awkward exchange before she offers to pick up groceries on his behalf, which he graciously accepts. His shopping list consists of a single item: whiskey, accompanied by ice cream sandwiches.

As Ivan Schrank (Rhys Ifans), Roger's friend, drops by to invite him to a barbecue at Eric Beller's (Mark Duplass) place, Roger finds himself in unfamiliar territory. The party atmosphere is palpable, but he remains visibly uncomfortable, and Eric's hostility towards him only adds to the unease. A chance encounter with Beth (Jennifer Jason Leigh), an ex-girlfriend, leads to a promise to meet up for drinks. When she presses him on his motivations, Roger confesses that he's in Los Angeles solely to indulge in a period of inertia. Her words of wisdom, acknowledging it takes bravery for a man in his mid-forties to eschew ambition, resonate deeply.

Meanwhile, Roger reaches out to Florence, inviting her to join him for a drink. Given his lack of driving skills as a New Yorker, she kindly offers to pick him up from his location. A brief stop at her apartment ensues to collect her forgotten purse before they head out. As the evening wears on, their initial drinks give way to an unexpected encounter that will forever alter the trajectory of their lives.

As the evening wears on, Eric's frustration boils over as he relives the agony of Roger's decision to reject a major label recording contract fifteen years prior. Eric can hardly fathom how Ivan, still reeling from the devastating loss, could even deign to speak to Roger again. But Roger remains steadfast in his conviction that compromising their art would have been an insidious betrayal.

Meanwhile, Roger's attention turns to Mahler, whose lethargy has him deeply concerned. A trip to the vet reveals a shocking diagnosis: auto-immune disease. As Florence tends to Mahler's treatment, Roger finds himself inexorably drawn to her, despite his initial reluctance. The more they spend time together, the deeper their connection runs, with Florence surrendering to the thrill of being with Roger.

Later, when Roger meets up with Beth for drinks, he's met with an awkwardness that's almost palpable. Beth's hazy recollections of their past only add to her discomfort as Roger delves into the minutest details of their time together. His musings leave Beth aghast - they would have probably settled down, started a family - before he asks her out on a date, only to be rebuffed with a firm "terrible idea" and a hasty request for the check.

As Florence and Roger's relationship reaches a fever pitch, their argument erupts into a heated display of emotion. He berates her for always returning to him despite his protestations that he doesn't want to get involved. The next day, Roger is wracked with remorse as he calls Florence, only to find her drowning her sorrows in her apartment alone. She confesses that she's scheduled an abortion for the following day, and Roger convinces her to let him accompany her to the clinic. Without a driver's license, Ivan reluctantly agrees to chauffeur the pair to the procedure, after which Florence spends the night at the clinic under general anesthesia.

As the evening wears on, Roger's life takes an unexpected turn with the arrival of his college-age niece, Sara (Brie Larson), who has come to pack up her bags for a trip to Australia with her friend Muriel (Juno Temple). The duo brings with them a swarm of friends, and soon the house is alive with the sounds of revelry. Roger, eager to connect with his younger counterparts, indulges in substances that blur the lines between reality and fantasy. Ivan's arrival marks a turning point in the evening, as his argument with Roger reveals the depths of hurt and frustration stemming from the record contract. As the tension builds, Roger confesses his crushing guilt over inadvertently killing the deal, and both men bemoan the lives they never planned to lead. However, Ivan has found solace in his circumstances, and he shares a poignant truth: that they rarely discuss meaningful topics. This realization weighs heavily on Roger's conscience, leading him to reach out to Florence (unbeknownst to her) with a heartfelt confession of his feelings.

The next day, Sara extends an invitation to join her in Australia, and Roger seizes the opportunity to escape his troubles. As he prepares to depart, he makes arrangements for Mahler's care before having second thoughts at the airport. Instead, he takes a detour to visit Florence at the hospital, bringing her back to her apartment where their relationship reaches a crossroads. The film concludes with Florence listening intently to Roger's voice mail, her emotions left to simmer as she ponders his heartfelt confession.