After losing her job, her house, and her long-term boyfriend, Gabby's roommate signs her up to be in a dating experiment. Little does she know, however, that her ex is in the experiment too! In an attempt to escape the chaos of her life, Gabby visits home and accidentally reunites with her childhood friend (and secret crush), Ian O'Connell. As she participates in the study and its hilariously awkward dates, Gabby finds her heart torn between the man she's comfortable with and the man who's had her heart from the beginning.