In 2003, a young Craig finds himself forging an unexpected friendship with retired businessman John Harrigan after the tragic passing of his mother. Tasked with simply reading to Harrigan three times a week, this unusual bond deepens over time. By five years later, Craig, now a teenager, and Harrigan share a genuine camaraderie.
As Craig embarks on his high school journey, he encounters supportive teacher Ms. Hart who provides him with guidance when he becomes the target of school bully Kenny Yankovich. When a lottery ticket gifted by Harrigan wins him $3,000, Craig celebrates by buying Harrigan his very own iPhone for Christmas. Initially hesitant to embrace the new technology, the elderly Harrigan soon discovers the joy of his new device.
However, the happiness is short-lived as Harrigan passes away, leaving Craig heartbroken after losing a dear friend. During the funeral, in a poignant act of affection, Craig smuggles Harrigan's phone into the coffin. Later, he learns of a significant inheritance from Harrigan's will: a trust fund of $800,000 intended to help Craig pursue his education and writing aspirations.
After calling Harrigan's phone to express his gratitude, Craig is shocked to find an unexpected text waiting for him the next day. His father dismisses the message as a mere glitch in the phone. Moving forward, Craig navigates the trials of adolescence, attending a dance with his crush and encountering Kenny again, who threatens him over alleged betrayals regarding drug dealings, leading to Kenny's expulsion.
Overwhelmed and distressed, Craig calls Harrigan's phone to share his fears and expresses a longing for advice, declaring, > "I wish that you were here just to give me some advice." In an eerie twist, the next day, Kenny is discovered dead from a fatal fall from his bedroom window, leaving Craig in shock.
In an effort to escape the turmoil, Craig upgrades his phone at an Apple store, abandoning his old device. With determination, he graduates high school and heads to Boston for college, aiming to major in journalism. However, unexpected news from his father shatters his solace—Ms. Hart has tragically lost her life in a car accident involving a drunk driver, Dean Whitmore, who faces light consequences despite a history of offenses.
Fueled by anger, Craig uses his old phone to send a distressing message to Harrigan, wishing death upon Whitmore. To his astonishment, he learns that the driver has been found dead in suspicious circumstances. Curiosity drives Craig to investigate the rehab center where Whitmore was sent, leading him to discover unsettling details of the driver's demise linked to Ms. Hart.
In a heartbreaking moment, Craig reflects on Harrigan's once-offered wisdom, thinking perhaps the mysterious messages are Harrigan's way of encouraging him to move on. After visiting Harrigan's "secret closet"—a hidden shrine to his mother—Craig makes his way to her grave to seek forgiveness.
Struggling with grief, Craig finds himself at the edge of the town quarry, wrestling with the desire to succumb to despair. Instead, he ultimately chooses to cast his phone into the depths of the water, symbolizing his wish to leave the past behind. As he walks away, he contemplates his future, vowing that when his own time comes, he wishes to depart with his pockets empty, ready to embrace whatever lies ahead.
