Valerie (Michaela Watkins), a successful psychiatrist, decides to divorce her husband after discovering he has been cheating on her with a younger woman. Taking her high school daughter Laura (Tara Lynne Barr) with her, she decides to live under the same roof as her brother Alex (Tommy Dewey), who runs a popular dating site. While Valerie tries to raise her daughter Laura with the support of her brother Alex, she also gets swept into a new relationship adventure through Alex's site.