Andy Brewster, an aspiring entrepreneur from California, embarks on a journey across the country to promote his organic cleaning product, Scieo Clean. His attempt to impress Kmart executives during a presentation ends in disappointment, leaving him to return to New Jersey to visit his mother, Joyce. While he portrays a successful facade, Joyce, still grieving her late husband who passed when Andy was just eight years old, believes he fled home to escape her. During their time together, Joyce shares an old home movie that reveals a surprising connection to a man named Andrew Margolis, her high school boyfriend.

In a twist of fate, Andy uncovers that Andrew Margolis is still single and working in San Francisco, prompting him to persuade Joyce to accompany him on his business trips to meet potential clients—including a reunion with her former flame. Reluctantly, Joyce and Andy plan their journey, with stops in Virginia, Texas, Santa Fe, Las Vegas, and finally San Francisco. Although Andy initially resists including a visit to his ex, Jessica, in Nashville, he eventually gives in.

As they navigate their travels, tensions rise. At one point, Joyce, while trying to be supportive, frustrates Andy with her unsolicited advice during a business meeting, leading to a heated argument. After an incident that leaves him with a black eye, Andy confesses his feelings of failure to Joyce while dining at a steakhouse in Texas, compelling her to take on a ridiculous eating challenge for free dinner. This light-hearted moment reinvigorates their bond, with Joyce earning respect from a passerby, Ben Graw, who shows interest in her.

Their adventures take them to the Grand Canyon and a playful detour in Las Vegas, where Joyce’s luck at the slot machines allows her to splurge on new earrings. As Andy gears up for a crucial presentation to the Home Shopping Network, he recalls his mother’s advice and impresses the executives by dramatically demonstrating the safety of his product—a moment that brings a glimmer of success.

However, the trip takes a difficult turn when Andy reveals the true reason for their meeting in San Francisco: to introduce Joyce to Andrew Margolis. While this revelation initially hurts Joyce, their emotional journey culminates at Andrew’s home, where they discover bittersweet news about their past relationships. After saying their goodbyes, Andy witnesses Joyce’s unexpected phone call to Ben, suggesting that their journey may just be the beginning of new chapters for both of them.