Ramona was a bartender at a bar visited by Harry Wilson and Ryan Matthews during a guys' night out. Ramona sat by with amusement as Harry got drunk and ruined every chance for Ryan to pick up a woman in the bar. By the time Harry was ready to leave, all of Ryan's prospects had already left. However, Ramona slipped Ryan her phone number.
They began dating, but when Jen Clark crashed their date, Jen became jealous. Jen visited the bar where Ramona worked and insulted her, telling her that she looked old and that Ryan was only dating her out of pity. Ramona was clearly annoyed with her behavior. She later told Ryan what Jen had done, at which point Ryan confronted Jen. Ryan and Jen decided on being exclusive and Ramona was left out of the equation.