On her debaucherous 40th birthday, chronically underemployed serial relationship killer Jackie Rosenblum meets magnetic dreamboat River Manning.

Things take an unexpectedly wild turn on River and Jackie's first date.

River and Jackie make a pact to swap places in the dating world and make each other over for their new online profiles.

River and Jackie go on dates arranged by each other and wind up deepening their friendship in some unusual ways.

Jackie and River take a revealing journey to the past while waiting out the effects of pot cookies. Guest star: Paige McKenzie (Haunting of Sunshine Girl)

Jackie and River toy with the idea of having a baby; Jackie's mother makes a stunning revelation.

Jackie & River run into their off-the-rails "exes" and decide to set them up, which has a surprising effect on their own relationship.