Senior citizen Ben (Robert DeNiro) shoots a video resume for an intern job he wants. He's responding to a flyer asking for senior citizens to apply for an internship via a video stating why they should be hired. He says he's a 70-year-old widower living a comfortable life but feels he needs to be more productive. He gets a call for an interview.
The company is called 'About The Fit' and is run by Jules Ostin (Anne Hathaway). Originally started from her kitchen, the online clothes retailing company now has gained more than 200 employees since it's founding only 18 months. We first see Jules answering a customer service call from a bride complaining that her bridesmaids dresses are the wrong color. Jules takes full responsibility, is very helpful, promises to fix the glitch and even gives her own number to the bride. She moves around in her office on a bike, rarely has time to stop and celebrate co-workers birthdays in the office or have a complete conversation with her mother.
At his interview with a series of people, Ben reveals that he used to work for a company that made phone books. The interviewer (Nat Wolff) also asks him where he see himself in the next ten years and then realizes the question really doesn't apply. He tells him that he did great in his interviews and video and is quite overqualified for the job.
Jules co-worker Cameron (Andrew Rannels) informs her that Ben is going to be her intern, and they had jointly agreed to the outreach program a few month ago. She asks and is advised that the minimum time for her to put up with him is six weeks, since she has to make an example.
Ben takes care to dress impeccably for his first day at work. Jason (Adam Devine) shows him and three other interns (two senior citizens including Celia Watson as Doris, and a young man, Zack Pearl as Davis). While Davis sets up his table with various gadgets, Ben's table has basic stationery and a simple calculator and watch. The other employees are friendly and help him start up the computer.
He is informed by Jules assistant Becky that he has a meeting with her at exactly 3.55 pm, and he should be prompt because there's another meeting at 4:00 pm. Becky also tells him to talk fast and blink a lot, because her boss is disturbed by people who do not. In the meeting, Jules informs him that she will not have much for him to do. However, she will email him if something comes up.
He does not hear from her for a few days. Nonetheless he makes himself productive, getting to know the ropes around the place and learning how to deal with the technology. He helps whomever he can and is referred of Mr. Congeniality by Cameron. In addition, he also gives old school sensible advice to the youngsters when they need it, such as telling Jason to talk properly to Becky for cheating on her since his evasive text messages did not get any response.
His first task assigning email is from Becky, asking him to have Jules jacket cleaned. She spilled soy sauce on it, but she's wearing it and he has to get it from her. In the office, Cameron is telling Jules that their investors think that its all going too fast at About The Fit and a seasoned CEO could handle affairs better and help them keep up with their success. Ben overhears this. Jules is clearly upset at the thought of having a boss although she admits that they have problems. Cameron advises her to look at the list of CEOs they have and take her time to meet them and decide on one.
Ben starts to be noticed more and more around the office especially after he is lauded by having a bell rung for him (an office practice to highlight good performance) for clearing out a desk that was the office dumping spot and routinely got on Jules nerves. The office masseuse Fiona (Renee Russo) gives him a massage and its evident he is attracted to her, as Davis needs to give him a magazine to put on his lap commenting he is not as old as he thought.
One day Ben notices the driver who drives Jules around drinking on the job and tells him to inform Jules he can not drive, or he will have to spill the beans. Ben takes over. She informs him that she can not sit in the front and that she will be making calls in the back, the contents of which should stay confidential. Her first call is from her mother who informs her that women who sleep less are more likely to gain weight. They clearly don't have a great equation. She calls Cameron next and tells him she is meeting one of the CEOs on the list. The meeting is very short. Cameron isn't convinced she is really trying. Ben has meanwhile bought her a cup of soup having realized that she hadn't eaten. While dropping her at home, he tells her he believes she should rest more and when she is in doubt she should remember that she started the company from nothing.
At home, we see her daughter Paige and husband Matt, who is a stay at home dad. He looks disappointed the CEO thing did not work out. He is very involved, and their daughter see