A group of kids on the brink of adolescence gather together in a circle to engage in a game of spin-the-bottle. The rules are simple: whoever the bottle points to must join the spinner in a closet for a duration of seven minutes. When Charlie spins, he's hoping for a chance with a stunning girl, but fate has other plans—a Goth girl cloaked in black is the chosen one. Inside the closet, she confesses her feelings for him, undoes his shirt, and scratches his chest, inflicting unexpected pain. Despite her advances, Charlie firmly rejects her, prompting her to hurl him out of the closet and declare in fury, “You will never find love and be in pain forever!” With that proclamation, a curse is placed upon him.
Fast forward nearly two decades, and we find Charlie Logan (Dane Cook) at the beach, locked in a passionate moment with a beautiful woman who expresses her love for him in a rather unconventional way—by licking sand off his body. However, despite her affection, Charlie struggles with the ability to reciprocate those feelings verbally. Later, he converses with his best friend Stu (Dan Fogler), both of whom are doctors: Charlie as a dentist and Stu as a cosmetic surgeon renowned for breast enhancement. Stu expresses his frustration, implying that maintaining a relationship sometimes requires a bit of deception.
At a wedding where Charlie's ex-girlfriend is tying the knot, he observes a troubling pattern—every woman he dates swiftly moves onto another man. Amidst this, he encounters a captivating brunette named Cam, sparking a connection that delights Charlie. Cam, who hilariously works as a penguin keeper at a zoo, chips a tooth in a humorous mishap involving her brother, leading her to seek Charlie's dental assistance. Their relationship blossoms, but Charlie’s fears about being a "good luck charm" haunt him, creating intent to disprove the theory by engaging with an overweight woman named Courtney, an experience that ends up backfiring dramatically.
Despite a myriad of misadventures, including a comical attempt to shower Cam with extravagant romantic gestures—like showing up at her workplace dressed as a penguin—Charlie’s insecurities grow. He mistakenly believes Cam is involved with another man named George, leaving him desperate enough to confront this supposed rival with an inflatable penguin, which ultimately results in security intervention and the collapse of his budding romance with Cam.
In a moment of desperation, Charlie recalls the Goth girl from his youth and the curse she placed upon him. He locates her in hopes of lifting the spell. She reflects that her actions were those of a foolish girl and suggests that true love will find its way naturally. Realizing this connection may not exist with Cam, he tentatively pursues a friendship with a renowned penguin expert whom Cam admires. Their bond seems promising until Charlie learns Cam is on her way to Antarctica with the penguin guru, who he fears may become her partner.
With urgency, Charlie purchases expensive, first-class tickets to track her down at the airport, plunging him into a frenzy as he navigates various obstacles to reach her. Just in time, he finds Cam and presents her with an engagement ring box containing a pebble—symbolizing the way penguins find their mates. Cam is moved by the gesture, and they embrace lovingly.
Meanwhile, the Goth girl discreetly removes a pin from a voodoo doll resembling Charlie, indicating her lingering influence over him. As the movie concludes, viewers are left with a humorous glimpse into Stu and his new girlfriend's antics while house-sitting for Charlie and Cam during their trip to Antarctica, instilling a light-hearted sense of closure to the wild romantic escapades.
