A sheltered New England girl relocates to South Florida and describes her online dating adventures in a world of perpetual vacationers, where values are skewed, lines are blurred, and her ideas about relationships indefinitely change. Dana, better known as her username, Dana Dane, has horrible luck meeting the man of her dreams. She recruits her promiscuous, gold digging friend, Missy, to help her navigate the online dating waters. The two women find friendship and self-discovery through a series of exploits, sharing their dating woes with both onscreen correspondence, and in person mishaps. After enduring more than her fair share of dating disasters, Dana Dane nearly gives up on finding romantic bliss until a blast from the past unearths a whirlwind of feelings from a love that she thought she had lost forever. Could it be possible that while she was searching for love, love may have just found her?