Watch LookMovie. “The Pretty Waitress” follows Jacob, a shy teen who finds himself mesmerized by the waitress. His friend Mark encourages him to ask her out. When Jacob finally attempts it, Mark’s encouragement turns into pressure and derails him. As Jacob embarrassment turns into frustration, he has to confront his fear and speak up for himself. What begins as simply telling a girl she’s pretty, turns into a step towards Jacob finding his voice.