For two seasons, we’ve watched aspiring comedian Pete Holmes struggle through cringe-inducing, awkward moments (both personal and professional) in HBO’s Crashing. Season 3 is no different, but for the first time in his short-lived career, he’s tasting the sweet nectar of success. This season, we see Holmes explore other comedic avenues far removed from the NYC comedy scene, all while he dives head first into a new romance that challenges… well pretty much everything he holds dear. We spoke to Holmes, newcomer Madeline Wise (aka Kat), and Executive Producer Judd Apatow about what happens when Holmes’ life is shaken up in unexpected ways. Watch our interviews below, and stream new episodes of HBO’s Crashing, Sundays at 10/9c.