Barry Egan, portrayed by Adam Sandler, is a single man running a quirky business that sells themed toilet plungers along with various novelty items. His life is anything but cheerful; with seven overbearing sisters constantly mocking and emotionally abusing him, he endures a profound sense of loneliness punctuated by moments of rage and despair. One fateful morning, his monotonous routine is disrupted when he witnesses an unusual car accident. As if that wasn't enough, he picks up an abandoned harmonium from the pavement and has a chance encounter with Lena Leonard (played by Emily Watson), a colleague of his sister who had set up the meeting after recognizing him in a family photograph.
In an attempt to cope with his solitude, Barry reaches out to a phone sex hotline, only to find himself the victim of an attempted extortion by the female operator who sends her four henchmen—who just so happen to be brothers—to intimidate him into paying up. This unexpected mess complicates his growing affection for Lena as well as his plans to exploit a loophole in a promotion by Healthy Choice to gather frequent flyer miles by purchasing massive quantities of pudding, inspired by the true story of David Phillips. When Lena departs for Hawaii on a work trip, Barry makes the spontaneous decision to follow her.
Upon arriving, he calls one of his manipulative sisters in a bid to learn Lena's whereabouts. When his sister attempts another emotional manipulation, Barry's frustration boils over, demanding she divulge the information. In a delightful turn of events, Lena is thrilled to see him, leading to an intimate pillow talk session where Barry initially claims he’s in Hawaii on business by pure chance. However, he soon confesses that he was truly there to pursue a romantic connection. As their relationship blossoms, Barry begins to experience a sense of relief from his previously tormenting emotional isolation.
After their return home, Barry faces a sudden spiral back into chaos when the four henchmen retaliate by crashing their car into his. Though Lena sustains minor injuries, Barry channels newfound bravery and swiftly defeats the goons in a matter of moments, showcasing a surprising assertiveness that contrasts sharply with his previous demeanor. Fearing that Lena would leave him if she learned of his phone sex hotline troubles, Barry leaves her at the hospital and decides to confront the situation head-on. He calls back the hotline, expecting to speak to a "supervisor" but instead finds himself face to face with Dean Trumbell (Philip Seymour Hoffman), a mattress store owner who initially tries to intimidate him. To his shock, Barry turns the tables, standing firm and compelling Dean to cease all harassment.
Ultimately, Barry resolves to come clean to Lena about his phone sex escapade, seeking her forgiveness while promising to accompany her on all future business endeavors using his well-earned frequent flyer miles. With her unwavering support, they share a heartfelt embrace. In a tender moment, Lena approaches Barry in his office as he plays the harmonium, wrapping her arms around him and exclaiming, “So, here we go.”
