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A man grieves the death of his wife by going on a cross country road trip with his dog and two friends to fulfill a childhood dream of surfing in Newport Beach.
When Andrew Miller’s wife, Lucy, leaves him unexpectedly—leaving only her wedding dress and lingerie hanging in their closet—he goes to great lengths to maintain his life in Washington DC. But when Lucy dies a year later and Andrew receives a nearly two-million-dollar life insurance payout, his friend Brian helps him understand he has an opportunity to start over. Andrew decides to leave everything behind and drive with his dog across the country to go surfing in California, something he has always dreamed of but never tried. As he departs, Brian shows up and says he’s going with him. While Andrew is grieving the woman he loved, though, Brian just wants to have fun, finding a new woman in every city they visit.
Once they arrive in New Orleans, Andrew inadvertently stumbles into a funeral. Mortified, he goes to a bar across the street. Gina, the niece of the deceased, goes to the bar to use the restroom and starts talking to Andrew. There is instant chemistry between the two. Gina is at her own crossroads in life, having just broken up with her boyfriend and looking to escape her position as a paralegal.
The two run into one another again in Sedona, where they start a romance. Gina decides Andrew is not ready for a relationship, though, and continues on her trip. When he sees Gina leave, Andrew goes on a run and begins to discover the joys of trying new things. He and Brian continue on their journey, but not before picking up two new passengers: Arnie, who is Lucy’s brother, and Taylor, who was traveling with Gina but got left behind.
In Newport Beach, they all go surfing, marking the start of a new life. While they’re sitting on their surfboards, a large great white shark begins circling them and bumps into Andrew. Andrew punches the shark in the nose! A man that punches a shark is a man that can take life in any direction he chooses.
Several years later, Andrew is working on a PhD and teaching courses at UCLA. He gets an invitation to Arnie and Taylor’s wedding in Newport Beach and discovers Gina is a bridesmaid. When he goes to say hi, Gina reveals she is married with a child and working on her law degree. Andrew is happy for her and returns to his life in Santa Monica. He talks to his mom—who has been divorced four times and acts as his confidante throughout the film—about getting onto some of the dating sites and then goes surfing. Silhouettes of sharks are everywhere.