The movie starts off with Ben (Robert DeNiro) telling us about himself. He’s a seventy-year-old widower living a comfortable life but feels he needs to be more productive. He answers a flyer asking for senior citizens to apply for an internship via a video stating why they should be hired. 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 hires about 220 employees having grown that much in only 18 months. We first see Jules answering a customer service call from a bride complaining that her bridesmaids’ dresses are the wrong colour. 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 realises 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 coworker 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, and he should be prompt because there's another meeting at 4 pm. Becky also tells him to talk fast and blink a lot, because her boss is weirded out 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 practise 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 realised 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 seems loved and happy. Jules falls asleep in her daughter's bed, and when she returns to her own, Matt is asleep and too tired to make love.
Becky calls Ben the next morning telling him Jules driver is not responding to her calls, and he needs to pick her. Matt invites Ben in for a coffee while he waits. Paige and Matt seem to like him. Ben quietly observes the dynamics at home and the school playground where the other moms seem to look down on Jules for being a busy career woman while she is dropping Paige. Later on, she handles a situation at their warehouse, and he seems impressed.
Ben goes to see Fiona at her office where she gives him a foot rub. Davis confuses it for a blow job and runs away. Lewis (Jason Orley) has to deliver a package to an address he thinks may be Jay Z’s, and Ben gives him sartorial advice. Jason also seems to have made progress with Becky after talking to her like Ben suggested.
One day while Jules is working late, and Ben is working on his computer waiting around to drop her home, she brings over her pizza to talk and eat with him. He asks her about a meeting she had with another CEO that didn't go too well either. He tells her about his previous employment, which was actually in the same building before phonebooks became redundant altogether. They bond, and she helps him set up his Facebook account, and friends him, finding out more about him in the process.
The next day, Doris comes to pick her up. The minimum period she had to put up with an intern, six weeks, is over, and Ben has been transferred. Doris can not drive, and Jules takes over, while calling Cameron asking for Ben back. She goes to find him in a coffee shop where he is picking up coffee for the department he currently works at. She helps him with the coffee, apologises, tells him she feels calmer in his presence and offers him his old job back. She also moves him closer to her workspace, right next to Becky. Becky starts crying because she is already overwhelmed with her workload and is threatened by the new development as she is a Business graduate from Penn, who can't seem to do anything right. Jason steps in to comfort her and gives her Ben’s hanky, while Ben calms her down, so she isn't threatened by him.
Ben begins to give insightful opinions and shows that he has useful experience. Jules gives him more and more responsibility, surprising Cameron. Ben also points out Becky’s input and degree encouraging Jules to say something nice to Becky. Davis, who had a deadline for moving out from his parents, declares he is moving to Philadelphia to crash with his cousin. Realising his commute will be crazy, Ben offers him a room in his house. He is impressed with Ben's house and wardrobe, especially his affinity for handkerchiefs which Ben insists gentlemen must carry.
The next morning at Jules’, Matt turns down a trip to San Francisco where Jules has to meet a CEO on account of school activities Paige is looking forward to. Jules has a work crisis to deal with, during which a phone call from her mother makes her mad. She writes a ranting email about her mother to Matt but accidentally sends it to her mom. She asks her coworkers to do something about it. Ben volunteers to go to her mother's house and delete it from her laptop before she comes back from work at 5.30. Jason, Davis and Lewis accompany him and after some glitches they get the job done. That night Jules takes them out for drinks and gets to know them for the first time. Meanwhile, Ben and Fiona have gotten close.
When Ben goes to pick up Jules the morning after that, he finds Matt sick and Paige in tears at the prospect of going to a party with a sitter, so he agrees to take her instead. In a very dignified manner, he defends Jules career and professionalism in front of the catty moms making it sound like partly their victory that one of their own made it so big.
Paige is not feeling well, so they leave the party early. However, he finds that Matt was faking his illness to meet another mom who he is clearly having an affair with. Since Paige is asleep, Ben waits for Matt’s return and drops a sleeping Paige off when he is back. Matt asks Ben’s take on the CEO situation saying he hopes it will be good for them. Ben replies that that a CEO will not be able to fix what is wrong in their house. Matt seems unnerved, but back at the office (where Jules is finally part of a coworkers birthday celebrations) Ben is in worse shape as his blood pressure acts up, and his coworkers show concern for his health.
They take off for San Francisco the next day. Jules tells him she knows there's something he isn't telling her since he doesn't look directly at her and blinks little. He admits to being a softy despite his manly exterior and suggests they enjoy their first class plane ride.
That night a fire alarm goes off in their hotel. When Ben escorts Jules back to her room, it is clear she wants company. She invites him in and asks him about his marriage, eventually confiding in him that she found out 18 days ago that Matt was cheating on her. Ben told her he saw them the previous day as Jukes breaks down. He comforts her and tells her she should only hire the CEO if she wants to, not for anyone else, and she should be able to have both a great career and a good marriage.
The next day, her meeting with the CEO takes longer than most of her meetings so far. When she is done, she tells Ben that she hired him on the spot, though the CEO told her to sleep on it. Back at home she informs Matt and tells him she thinks it will be great for ‘us’. He asks who the us refers to, and she clarifies that she meant Jules and Matt, not About The Fit. However, she breaks down as she is taking a bath that night, showing she is clearly unhappy with her decision.
She visits Ben in the morning, and is pleasantly surprised to see Davis and then Fiona emerge from his apartment. She tells him it still feels like it is a right decision. He recalls the time at the warehouse and tells her no one will have the commitment she has to her company, even if they have more experience. He doesn't see how giving up her company in hopes that her husband will stop having an affair adds up, and tells her she came here because she wanted to hear it. She adds that it is also because he is her best friend.
The bridesmaid from the customer service call she took at the beginning of the movie has sent her pictures of the bridal party and a thank you note. Also, the CEO she met in San Fransisco sent her some flowers. She asks Becky to put him on the phone in a decisive voice. Just then, Matt walks in saying she should not hire the CEO for him. She needs to do what's right for her. She informs him that she is aware of his affair as he is about to admit to it and asks if it is over. They recommit to each other and promise to do better. Jules tells him she was going to call the CEO and tell him that she changed her mind. They kiss. She goes after Ben to tell him that she changed her mind, to find him in a Tai Chi group. She joins him, finally letting herself relax.
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