In the 1950s, a feral puppy named Toby is whisked away to the dog pound and quickly euthanized, wondering if "fun" truly is life's purpose.
His strong spirit is reborn and reincarnated as a newborn Retriever puppy in 1961. Toby leaves his cage at a puppy mill and is found by two garbage men who plan to sell him. They leave to drink, and Toby is spotted locked inside their pick-up truck by a young boy named Ethan and his mother, who rescue him from heatstroke. After they convince Ethan's father, the dog is allowed to stay and is renamed Bailey.
Bailey and Ethan bond quickly, especially over the summer when the family visits Ethan's maternal grandparents' farm, and Bailey now believes Ethan alone is his purpose. Years pass, and after several attempts at advancing in his job fail, Ethan's father has become a deadbeat alcoholic.
Over the summer, Ethan goes to a fair with Bailey and meets Hannah, whom he quickly begins dating. Ethan and Hannah spend their summer happy together though their senior years are upcoming, but they plan to go to the same school; Ethan getting a football scholarship and Hannah following him on an academic one. When he goes home one night, Ethan's father is drunk and shouting at Ethan's mother. He turns on Ethan then and when his mother tries to keep them separated, he shoves her to the ground. Ethan orders his father to leave and never come back.
Later, at a game watched by scouts, Ethan is offered a scholarship to Michigan State, but that night a vindictive classmate named Todd throws a lit firecracker into Ethan's house as a prank, which unintentionally results in a house fire. Bailey alerts Ethan, who goes to save his mother. Unable to get out of the door, they head out through his mother's bedroom window upstairs. Ethan first lowers her with her sheets to the neighbors below, then saves Bailey. However, he drops his rope and must jump, badly fracturing his leg and ending his athletic scholarship. Bailey attacks Todd, who is arrested by the police when firecrackers fall out of his pocket. Now, Ethan must go to an agricultural school where he will learn to take over his grandparents' farm. Falling into depression, Ethan breaks off his romance with Hannah before leaving for college, while Bailey stays with Ethan's grandparents. Sometime afterward, an aged Bailey is put to sleep at the veterinarian's office.
Bailey reincarnates into another dog life, a female German Shepherd police dog named Ellie, sometime in the late 1970s/early 1980s, while possessing full memories of his past lives. Ellie is partnered with a widowed officer named Carlos from the Chicago Police Department and works hard at "seeking" and "finding", now seeing the job as life's purpose. The two form a close relationship which ends after Ellie saves a kidnapped girl from drowning and is then fatally shot by the kidnapper.
Reborn again in the mid-1980s as a Pembroke Welsh Corgi, he forms a bond with an Atlanta college student named Maya who names him Tino. Maya is lonely, and Tino makes it his purpose to find her some happiness. She starts a relationship with a classmate named Al whom she begins seeing after Tino falls for Al's dog, a black and white Landseer named Roxie. Maya and Al marry and have 3 children. In love with Roxie, Tino is heartbroken when one day she does not return from the vet. As he lies sleeping, Tino thanks Maya for giving him one of his best lives.
Tino is again reborn and reincarnated, this time as a St. Bernard-Australian Shepherd mix, only to be taken in by a neglectful urban couple who name him Waffles. Waffles is dumped in an abandoned lot and sets off in search of a new life. He gradually makes his way to the country area where he spent summers as Bailey and joyfully reunites with his old master Ethan, who is now in his 50s, living a lonely life at his grandparents' old farm, which he now owns and runs. Ethan hands him over to the local animal shelter but soon has a change of heart and reclaims him, naming him Buddy. Buddy, sensing that he has finally found the true purpose of life, reunites Ethan with a widowed Hannah, and they get married.
Buddy convinces Ethan that he is his beloved childhood pet by performing some tricks and responding to key phrases that were known only to the two of them many years ago. The dog in voiceover tells the viewer that life is about having fun; saving others; not getting caught in the past or regrets; finding someone to be with; and living for today.
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