On a seemingly normal date with his girlfriend Karen, James gets smacked with a break-up. What's the reason? Because he's 'too nice'. Devastated and not wanting to be alone, he quickly jumps back into the world of dating, much to the annoyance of Sarah, the hostess of the restaurant he brings all his dates to. With help from his best friends and father, James must navigate through his insecurities to find a woman he can have an honest relationship with and trust not to break his heart again. Of course, everything gets complicated when Karen comes back into the picture.