Summer season at Steiner Mountain Resort continues as Moishe and Shirley join the group, disturbing Abe's peace. Susie tries to ward off a new friend while keeping a low profile at the resort. Midge jumps at the opportunity to redeem herself at B. Altman.

Susie lands Midge her first gig on television, but their victory is short-lived when they realize Midge is being punished for her past. Abe is increasingly unhappy in his dream job at Bell Labs while Joel continues to drown in work during late nights at Maisel & Roth.

The Weissmans arrive in the Catskills for their annual summer trip and attempt to settle into familiar patterns. Whispers of Midge and Joel's separation cause Rose to poke around her daughter's love life. Susie must adjust her summer plans in an effort to keep her and Midge's career momentum going.

Midge and Rose begin planning for Midge's future as Benjamin attempts to impress Abe. Joel stresses over his next move, while Abe is presented with some big decisions of his own. Meanwhile, Susie tries to smooth things over for Midge.

With Midge's secret now exposed to Abe, tensions between them are higher than ever. Summer is nearing an end with Susie fully immersed in her Steiner persona and Joel contemplating life as a bachelor. Rose takes advantage of Astrid's fragile state to learn some surprising intel about Noah.

Benjamin opens Midge's eyes to the New York art scene, and she ends up knowing more about art than she realizes. The Maisel and Weissman families come together for a tension-filled Yom Kippur dinner on the anniversary of Joel and Midge's separation. Meanwhile, a reluctant Susie turns to her family for help in advancing her career.

Midge and Susie continue building Midge's standup career despite Midge's reluctance to tell her family and friends. Abe and Rose enjoy a new lifestyle. Joel offers some business advice to his parents and makes an effort to do right by Midge.

Midge and Susie gear up for their first roadtrip, and quickly learn that the dynamics of going on tour are more challenging than they thought. Back in New York, it's business as usual while Midge is away, forcing her to wonder if her new life is worth sacrificing her home life.

Midge takes the stage for a foreign audience, while Abe and Rose find themselves in a new world. Susie experiences the repercussions of having a bad reputation in the business, as Joel regroups after quitting his job.

Midge puts her impeccable planning to the test as she helps Mary with her special day. Joel attempts to keep finances steady at Maisel and Roth and ends up on a treasure hunt. Midge's act flourishes, but Susie's finances take a hit. Back at Columbia, Rose finds herself out of her comfort zone when auditing classes.