Win a Date with Tad Hamilton!

Rosalee, a charming small-town girl, wins a date with her Hollywood crush, Tad Hamilton, through a charity contest. When Tad arrives in her hometown, their date goes surprisingly well, and they start to develop feelings for each other. However, things get complicated when Pete, Rosalee's best friend and secret admirer, tries to sabotage their relationship out of jealousy. As Tad and Rosalee continue to spend time together, they both have to confront their true intentions and make a choice between their careers and their growing connection. Will Rosalee choose the glamorous life of a Hollywood star or the familiar comfort of her small-town roots?

You can stream Win a Date with Tad Hamilton! on: Netflix

Some movies that have similar genres and were produced around the same time as Win a Date with Tad Hamilton! include I Now Pronounce You Chuck & Larry, 50 First Dates, High Fidelity, Yes Man, Juno, Chocolat.