Producer Jess sits down with Jen to dig a little deeper on the subject of heartbreak. If you haven't heard it before, Season 1 Episode 20 is where this conversation about surviving heartbreak opened. But during this opener for Season 2, Jess takes the story deeper, walking Jen down the "memory lane" of her most signficant heartbreaks. In this episode's artwork, Jen is pictured at a favorite family vacation spot, the summer before the first loss she discusses.