Cat (Krista Bridges) has a mediocre job, a mundane social life and her relationship with Freddy (Enrico Colantoni) has been, well...uninspired. Enter Richard (David Cubitt), Freddy's boss. Charming, gregarious, astute, and shockingly self-confident, he promises to be everything Freddy is not. Cat and Richard's brief encounter evolves into an affair. Overwhelmed by her own guilt, however, she breaks it off to make a final, sincere attempt to reignite the flame with Freddy with a romantic trip to wine country. Nothing, however, can prepare Cat for what happens when she finds out Richard - accompanied by his perky, perfect young girlfriend, Amy (Brooke Palsson) - is joining them.