Young tech entrepreneur Olivia Grassi has hit rock bottom. She's been dumped by her boyfriend/business partner, ousted from the tech company she helped create, and she's spending all her money on a lawsuit against them, both. She moves back home to Pasadena, California, where her best friend Shane suggests she creates a new dating app to get her life back on track. Olivia goes on a series of meetings to pitch her new dating app, but fails miserably because everyone she meets is terrified of her. Frustrated, but not out of the game, Olivia gets help from Shane and her family to make another attempt at selling her app. This time she gets set up with one of the biggest venture capitalists in the world, Alan Stevenson. However, this opportunity doesn't go far when Alan sexually harasses Olivia, and asks her to sign an NDA before agreeing to work with her. Rushing out of Alan's office, Olivia runs into Luke, who comforts her until her best friend Shane comes to her aid..