David takes a freelance job videoing a bris and accepts Getty's invitation to lunch in the city. Back home, Judy enjoys Ladies Night with new friends, while Sam goes on a blind date.

Getty prepares for his trial on insider trading charges. Nash's romance with Widow Horowitz heats up. Meanwhile, David wonders if he may be too suburban for Skye's new city lifestyle.

With the pressure of his trial weighing on him, Getty turns to an unusual confidante for moral support. One of Wheeler's students gets a little too close for comfort. And while Skye struggles to find her place on the New York art scene, David and Karen reconnect.

As Karen and Barry prepare to tie the knot, David finds himself grappling with a forlorn Nash, arguing parents, and stark choices for his future.