A rival ad agency courts Don, involving Betty in their attempt to lure him from Sterling Cooper. As the presidential campaign heats up, the agency looks for new ways to counter the latest Kennedy ads. Tempers flare over Peggy.

Don loses an account. Roger, stuck in the city for Labor Day weekend, attempts to cheer him up. Meanwhile, Joan has a night out on the town with her roommate.

Peggy is given a difficult assignment. Roger's work problems provide new opportunities for Don, and Pete grows more frustrated. Betty finds a new outlet for her growing dissatisfaction.