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 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.