Ben Whittaker (Robert De Niro), a wise and widowed 70-year-old man who is having a hard time finding something to do with his life during his retirement in Brooklyn, comes across a flyer for an online clothing business that is looking for senior citizens to work as interns. He seizes this opportunity by applying and receiving the internship. He is immediately paired up with Jules Ostin (Anne Hathaway), the perfect female business owner who is married, a mother and the one and only founder and CEO of the online store “About the Fit.”

Although it’s unlikely that a retiree would be looking for work to do and then end up settling with an unpaid internship in the fashion industry, the idea of it makes a cute story as Ben passes his knowledge about what it was like working at a phone book business down to Jules. Not only does Jules learn valuable tips from him, but Ben learns things from her about online businesses that have replaced businesses like the one that he used to work for.

It is obvious from the start that Ben and Jules are opposites; Ben is searching for excitement, while Jules cannot seem to get away from it—she wants nothing to do with the senior internship program. She tries to push Ben’s assistance away from her. In her eyes, all he will do is make her life even more chaotic than it already is. However, he ends up providing more help to her than she ever imagined.

Ben begins to serve as a taxi driver for Jules and is invited into her house before she is ready for work one morning by her husband Matt (Anders Holm), who is (a full time stay-at-home dad). Ben meets Jules’ daughter, Paige, and instantly adores her. Not only does he chauffeur Jules around, but he ends up driving Paige to a birthday party and back. It is then that Ben discovers Matt keeping secrets from Jules.

Whether it’s during rides in the car or late nights at work, Jules begins to connect with Ben and realizes why the rest of the office enjoys his company so much. While Jules is on an unsuccessful search for a replacement CEO for “About the Fit,” she asks Ben to assist her by departing on a trip to California with her. Jules meets with the proposed CEO that may take over her business and loves what he has to say, but is still unsatisfied.

Ben discovers that she also just recently found out about a secret affair, which was what drove her decision to step down from her position at work. He explains to her that spending more time at home is not going to solve all of her problems, and Jules is left with a decision of what’s more important to her: her husband or her business?