Oops I Did It Again is a show about an unfortunate young woman who hasn't had the best of luck in dating. After leaving her alcoholic boyfriend, her best friend try's to help by setting her up on a dating site. Little did she know that true love is never really accomplishable on apps like these, but maybe that isn't always the case. After she meets her first date, she realizes that this isn't helping but her friend convinces her to keep having disaster dates so she can finally have something interesting for her blog to stop her getting fired. But her first date appears to have liked her a bit too much...