The film follows small-town girl Rosalee Futch (played by Kate Bosworth), who works as a cashier at a grocery store in Fraziers Bottom, West Virginia. Rosalee dreams of finding true love and romance, idolizing the Hollywood actor Tad Hamilton (played by Josh Duhamel) as her ideal man.
Rosalee’s luck changes when her best friend and coworker, Cathy Feely (played by Ginnifer Goodwin), enters her into a contest to win a date with Tad Hamilton. To everyone’s surprise, Rosalee wins the contest and is flown out to California for her date with Tad.
Meanwhile, Tad Hamilton is a charming but shallow Hollywood heartthrob who is looking to repair his public image after a string of bad press. He agrees to the date with Rosalee as a publicity stunt orchestrated by his agent, Richard Levy (played by Nathan Lane).
During their date, Rosalee’s genuine sweetness and sincerity captivate Tad, and he begins to see her in a new light. Rosalee, in turn, is swept off her feet by Tad’s celebrity lifestyle and charisma.
As Rosalee and Tad’s relationship blossoms, complications arise when Rosalee’s childhood friend and secret admirer, Pete Monash (played by Topher Grace), realizes his true feelings for her. Pete, who has always been there for Rosalee, struggles to compete with the glamorous world of Tad Hamilton.
In the climax of the film, Tad must choose between his shallow Hollywood lifestyle and his genuine feelings for Rosalee. Meanwhile, Rosalee must decide whether she wants to pursue a future with Tad or explore a relationship with Pete, who has always been by her side.
Ultimately, love triumphs as Rosalee realizes that true happiness lies in being with someone who loves her for who she is, not for her celebrity crush. Tad, inspired by Rosalee’s authenticity, makes a heartfelt gesture to win her back, while Pete learns to express his feelings and pursue his own happiness.
“Win a Date with Tad Hamilton!” is a charming and heartwarming romantic comedy that explores themes of love, friendship, and the pursuit of happiness. With its endearing characters, humorous situations, and feel-good message, it has become a beloved favorite among audiences looking for a fun and uplifting film experience.