Ben Whitaker (Robert DeNiro) is 70 years old. Retired. A widower. He worked all his life for a Brooklyn company that published telephone books. Once upon a time that was considered important; now, it's yet another outmoded technology that few people use. He's been retired long enough to be bored. He goes to Starbucks every morning, just to have somplace to go. He reads the newspaper. He has a daughter and a son-in-law and a couple of grandkids, but he knows better than to impose himself on them too frequently; they have their own lives. Yes, there's a pushy neighbor who comes on to him, but he's not interested in her. So what is he interested in? Ah, there's the rub.
He happens upon an advertisement for an internship specifically targeted at seniors. It's a start-up company where everybody is really young, and the idea is that some life-experienced folks might be good for balance in the workplace. Well, maybe. Right away there's the technology gap: no cover letters or written resumes; just videos sent to an e-mail address. If we want a personal interview, we'll contact you by e-mail.
Ben gets the internship. He's delighted. He's more than happy to break out his old-school wardrobe of suit, tie, and handkerchief folded neatly in the coat pocket. Ah, but times have changed. Everybody there dresses “casually,” which just looks sloppy and unprofessional to him. It's an online clothing sales firm, headed up by an energetic young entrepeneur, Jules (Anne Hathaway). The whole enterprise is pulsating with success; now there's over 200 employees, and they're all filling orders fast and furiously. Jules herself is always swamped, always late, and terminally exhausted. She loves what she does, but she no longer has time to eat or sleep or pay much attention to her husband, Matt (Anders Holm), who's become the house-spouse and stay-at-home Dad for their young daughter, Paige (JoJoKushner).
At first, though Ben is assigned to Jules, she doesn't have anything for him to do. But gradually, he finds little tasks that no one else will do: clean up the office “junk desk.” Offer to be the chauffeur for Jules' business meetings across town. Some of the younger men around the office find themselves going to him for advice, as they would a kindly grandfather. Ben doesn't mind. Though his technology awareness is not exactly up to speed, he's observant, he likes people, he listens carefullly, and he doesn't answer more than he's asked. Before long, he's become a personal confidant of Jules, which puts him squarely into situations where an intern normally wouldn't have any access: such as taking Paige to a birthday party. Such as overhearing the discussions about possibly hiring a CEO, to take some administrative burden off of Jules. Such as noticing the tension between Jules and Matt, and then accidentally witnessing part of the reason why they're having difficulties: he's having an affair.
Yes, what began as lighthearted humor now turns pretty serious, as Ben evolves into a kind of father-confessor figure, though still maintaining emotional distance while in close proximity to a drop-dead gorgeous young woman. (It helps that a more “age-appropriate” suitor has also arrived on the scene: Rene Russo as the company masseuse?)
Director/Writer Nancy Meyers has her finger on the pulse of contemporary culture, from Millenialists to Baby Boomers, and her deft comic touch just adds to the enjoyment.