At his mother's, Walter pulls a travel journal their father gave him out of the box. Then, their mother, Edna, pulls out a framed newspaper article about Walter's days as a teenaged skateboarder, complete with a mohawk. Edna alludes to the fact that right after his father died, Walter worked at a Papa John's.
Walter goes back to work, where Hernando shows him a negative that has a boat in it. As Hernando gets off the elevator, Ted gets on and makes fun of the action figure Walter's sister gave him. Suddenly, in a fantasy of Walter's, Ted tries to wrangle the figure out of Walter's hand, but Walter fights back and they get in a rowdy tussle, eventually flying out a window of the building and into a passing garbage truck. With superhuman powers, Ted jumps out of the truck and skateboards on his feet through the city streets, with Walter following him.
Walter is jolted back into reality, back in the elevator. Ted laughs at how spacey Walter is and gets off, as Walter gets a call from an unknown number on his cellphone. It's the representative from eHarmony, who wants to help Walter fill out his dating profile. "If you work with this girl, why don't you just humanly invite her out?" the representative asks Walter. Walter tells him that he wants a more accidental romance, like the one described in the song "Escape (The Piña Colada Song)."
As he sees Cheryl walking towards him, Walter hangs up on the eHarmony representative. He shows Cheryl the picture of the boat with the name on it. She pulls out her phone to look up the name of the boat on the internet, then tells Walter that she's going to pick up her son at the park where he's skateboarding. When she invites him to walk with him, Walter agrees.
On the street, Cheryl tells Walter that she used to work at Nabisco, then moved to the magazine. They discuss the fact that Life is a nice place to work, both reciting the motto of the company—the same motto that was inscribed on the wallet Sean O'Connell sent to Walter. He shows her the wallet that Sean sent him, and tells her that he's never actually met Sean, but has been his point person at the magazine for 16 years.
Cheryl gets a call from her son's father, from whom she recently separated, but decides not to pick up. At the park, she calls their coworker Peg for more information on Sean O'Connell, while Walter talks to her son, Rich, and watches him play around on his skateboard.
Walter shows Rich some tricks on the skateboard, all of which are impressive. When she gets off the phone, Cheryl tells Walter that Sean could either be in Princeton, New Jersey or in Greenland. She then loads the information on the boat negative, confirming that it's a photograph of a boat in Nuuk, Greenland.
Walter has a fantasy that Cheryl professes her love for him and wants to run away together. Walter replies that he has the "Benjamin Button thing," where he gradually becomes an old baby, but this does not deter Cheryl, who still wants to build a life together. They kiss and we see them growing old in a large Southern house together, like in the film The Curious Case of Benjamin Button.
At the end of the fantasy, Walter becomes aware that he is spacing out again in the park. Cheryl has to run after Rich, who has run towards the street, but before she goes, she tells Walter that the song "Space Oddity" by David Bowie is a song about "going into the unknown," alluding to the fact that the bully-ish Ted Hendricks, who likes to call Walter "Major Tom" in reference to the song, has the wrong interpretation.
Back at the office, Ted asks Walter where the photograph is and tells him he wants to see it the next time he sees Walter. Walter agrees and goes down to his office, where Hernando tells him they should tell Ted that the negative is missing. Walter looks over at a picture of Sean O'Connell, and has a vision of Sean beckoning him towards him.
Resolving to go and find the negative, Walter leaves the Time-Life building and buys a ticket to Greenland. We see the plane taking off from a runway that says, "That is the purpose of life."
When he arrives in Greenland, the airport is a very small building and there is nearly no one around. He goes up to a car rental building and asks to rent a car, where he is given the choice of a blue or red car. He chooses the red one, and drives into the small seaside village.
Inside a small bar, a man is singing a lackluster karaoke version of "Don't You Want Me Baby." Walter sits at the bar and asks the bartender how the mail works. She tells him that helicopters bring mail to the ships as they pass by, and that the mail arrived on Tuesday. The man singing karaoke comes up to him drunkenly and invites him to sing the song with him, but Walter only sings a few lines in a nonplussed style. This angers the karaoke singer and they get in a fight.
In the middle of the fight, Walter recognizes the ring on the man's thumb from one of Sean O'Connell's photographs. As they sit down and have a beer together, the man reveals he's a helicopter pilot and tells Walter that Sean O'Connell may still be on the boat. Walter decides not to go with the man, who is visibly drunk.
Walter's main conflict in the film is how to merge his wild imagination and desire to do things out of the ordinary with his boring life and his tendency to get overlooked in the world. When he visits his mother's apartment, he looks over some of his old belongings, remembering that he once dreamed of traveling and had a passion for skateboarding. As a young person, it seems that Walter was able to harness his desire for individuality and adventure into certain activities, but this brave spirit has long since vanished in his adult years.
A major reason Walter seems to have left some of his more adventurous habits behind is that his father died when he was young. The travel journal that he finds in his mother's apartment reminds him that there were trips he wanted to take that he never got to pursue because of that loss. The article about his skateboarding as a teenager was something that made his father proud. The film does not directly connect father loss to Walter's lack of adventurousness, but it implies that some of the ways that Walter's ambitions have shrunk over the years has to do with the grief he felt in losing one of his biggest fans.
As he gets more embroiled in solving the mystery of the missing negative, Walter grows closer to Cheryl and learns more about her. He even gets to meet her son, Rich, who he bonds with about skateboarding. With their shared goal of tracking down Sean O'Connell, Walter and Cheryl begin to grow closer to one another in a gradual and romantic way, just like in "The Piña Colada Song," a source of romantic inspiration for Walter.
Eventually, the pressure to take a risk and stop living life by other people's rules becomes too great and Walter decides that he must go to Greenland in search of Sean O'Connell. He impulsively buys a plane ticket and flies across the ocean in a triumphant and cathartic montage set to an upbeat rock song. Inspired by his own vision of what could be, and determined to stop being a doormat for people he does not respect, Walter takes life into his own hands in an effort to realize his full potential.
A great deal of the comic mileage in the film comes from humorous contrasts between the triumph and grandeur of Walter's visions of bravery and a less than triumphant reality. This is used to especial effect when Walter goes to Greenland. We see him exhaling and smiling to himself as an empowering and climactic song plays, when suddenly the shot switches to him exiting a nearly empty and colorless airport, into the cold barrenness of Greenland. In The Secret Life of Walter Mitty, moments of personal growth and triumph are not necessarily as glorious as they first appear. Upon arriving in Greenland, Walter realizes that the decision to go was just the first step in a much more complicated process.