As Deborah prepares to accept an award in Montreal, Ava does her best to avoid her former employer

Deborah and Ava struggle to stay out of one another's orbits – especially when Deborah lands an unexpected opportunity

After learning there's a Late Night vacancy, Deborah makes sure everything – and everyone – is operating at its finest for her roast

Deborah is invited to hang with some of her favorite comedians, Jimmy finally lands a general meeting with Winnie, and Marcus recruits Ava for trivia

As Deborah contends with writer’s block and Ava with a broken heart, the pair decide to clear their heads in the woods

Deborah participates in a golf tournament to get face time with the cable affiliates who could decide her future

Deborah braces for Kathy's attendance at her Christmas party, while Jimmy and Kayla refuse to call it quits on the comedian's Late Night dreams

A calendar mix-up finds Deborah double booked . just as an unfortunate supercut of her most problematic early jokes starts circulating

As Deborah works to perfect her second run at Late Night, Ava receives a dream offer, and Jimmy and Kayla seek to grow their company