Ben (Robert De Niro) is at a lull in his retirement life. He has done those things that most of us desire in our retirement, but seems to feel bored and wants more. He happens upon an advertisement for senior interns at an up and coming Internet retailer, and this is where our story begins. Ben is plopped into the life of Jules Ostin (Anne Hathaway), the workaholic CEO of the company and reluctant recipient of Ben’s help. It takes time for Ben and Jules’ relationship to gain traction, but slowly these two dissimilar people develop a friendship. Ben takes on the role of tidying up the loose ends in Jules’ life, and, as he is given the chance, begins to contribute to Jules’ personal and business life in beneficial ways.
Ben is an upright guy who tries to share his wisdom and character with the coworkers around him. He works hard, dresses nice, treats people with respect, and, in turn slowly, gains the respect and friendship of those around him. Ben gets involved in a relationship along the way with Fiona (Rene Russo), the company masseuse. He takes on the roles of coworker, chauffeur, advisor, baby sitter, confidant, and friend for Jules.
As happens, when you get involved in someone’s life, Ben sees the flaws, highs, lows and heartaches of Jules’ life. The story leads us to a collision of crises in Jules’ life which involves her choosing a new CEO for the company and a defining point in her marriage. The scene where the resolutions collide is awkward, but allows the story to conclude and ends the movie where it started, more or less.