Though reeling from their meeting with Winnie, Deborah and Ava continue to clash over creative control on their writers' "retreat" in Vegas – all while pressure mounts to craft the perfect opening sketch.

During a dress rehearsal, Deborah experiences a shocking "first" that stands to throw her off her game. Meanwhile, Ava makes a connection at a sex shop. Then, Deborah takes the stage for her first episode of Late Night.

After a focus group reveals a weak performance with women, Deborah does whatever it takes to connect with the coveted demo, while Kayla and Jimmy set out to book a suitable guest, and Ava desperately tries to maintain the show's integrity.

Deborah receives the "Courage in Comedy" award, while Late Night books a last-minute guest. Meanwhile, Ava reaches her breaking point at the show.

With the show stuck in third place, Deborah pitches a bold new strategy for Late Night. Nina arrives in LA with a plan to shake up Ava's future. Meanwhile, as Jimmy struggles to keep everything together, Kayla receives a compelling offer.