For stand-up comedians Nicky and Jamie, their jokes mask insecurities and fears that threaten to tear them apart. Amanda and Ish, moved into together almost immediately after meeting, but two apartments and multiple break-ups later, they’re trying for the third time through this experiment. Emily is struggling to trust Andrew, while he is struggling to set boundaries with his meddling mother, Martha. Nothing short of radical honesty can give these couples a shot at a future together, and at the end of the 30 days, they will have to decide if they are in or out.