Everyone experiences heartbreak at different times in their lives. For best friends Ashley and Sydney, heartbreak came at the same time in both of their lives. In this series, the two women try to figure out out how to laugh through the pain, move forward and, ultimately, how to deal.

In this long overdue episode, Ashley and Sydney have some pertinent updates. Ashley is on a nudes journey, and Sydney has a Pavlovian response to a backwards hat. The women discuss Ashley's updated definition of loneliness, Sydney's relationship status, and attachment theory. At the end, they answer some listener questions for the very first time.