70-year-old widower Ben Whittaker, a retired executive from
DEX One, finds himself bored with retirement. He applies to fill the newly created position of senior intern at About the Fit, a fast-growing
e-commerce fashion startup in
Brooklyn. Ben impresses everyone and is one of three senior interns hired. He is assigned to work with
CEO Jules Ostin, who is somewhat skeptical at first and ignores him. However, Ben wins over his co-workers with his congeniality and his helpful advice on life and work. One morning, Ben organizes a longtime messy desk that Jules has been agonizing about, winning her good graces. Later, looking out a window, he notices Jules's chauffeur drinking. Going outside, he persuades him to leave. Ben acts as her chauffeur and drives Jules home. The next day, Jules's driver did not show up, so Becky asked Ben to pick her up, Ben asks Jules some personal questions, so she asks her
VP Cameron to reassign him. However, that evening, they bond when she discovers that he worked for almost 40 years in the same building that About the Fit now occupies. The next morning, Jules learns that Cameron has replaced Ben as her intern with Doris, a terrible driver who nearly crashes. Jules finds Ben and apologizes, begging him to come back, which he does. Jules starts assigning Ben work, and he helps lighten her workload. He also begins a relationship with About the Fit's in-house massage therapist, Fiona. When Jules accidentally sends a scathing email about her mother to her mother, Ben volunteers to take some co-workers to break into her mother's house to delete it from her mother's computer. They narrowly avoid getting caught by the police in the process. Ben becomes acquainted with Jules's family. Her husband Matt gave up his own very successful career to be a
stay-at-home dad to their daughter, Paige, when About the Fit started to take off. However, the marriage is slowly breaking apart as the couple grows more distant. When driving Paige home from a party, Ben discovers that Matt is having an affair. Meanwhile, Jules is under pressure to give up her post as CEO to someone outside the company because her investors fear that she is unable to cope with the unexpectedly high workload. Believing it will give her more time at home with her family, Jules gives in to the pressure. Jules asks Ben to accompany her on a business trip to
San Francisco to interview a potential CEO candidate. While there, Jules reveals that she knows about Matt's infidelity, but has not confronted him about it, as she is not ready to deal with it. To buy herself time to save her marriage, Jules decides to hire the prospective CEO, but Ben urges her to think about how much effort and passion she has used to build About the Fit. Matt unexpectedly drops in at Jules's office to try to persuade her to reconsider hiring a CEO as well. He also confesses to infidelity, saying that the affair is over. Sorry and ashamed, Matt wants to support Jules in her dreams and get their marriage back on track. Jules goes looking for Ben, wanting to tell him that she has changed her mind about hiring a CEO, but learns that he has taken the day off so that he can enjoy his
tai chi exercise group. She joins them and finally lets herself relax. ==Cast==