Lucky in Love (2000)

High school senior Chris "Lucky" Starr (Whett Wheetie) is in love...again. Unfortunately the object of his most recent infatuation doesn't even know who he is. Even more unfortunately though is that Lucky doesn't know who she is either. With the reluctant help of his best friend Stephanie (Saje Foxx) and the insistent help of his worst friend Trim (Terry Tuggs), Lucky hatches an elaborate series of poorly conceived, and even more poorly executed, schemes designed to manufacture that perfect first meeting with the new girl of his dreams.