13 episodesFirst aired 27 July 2008
Season two takes place between February and October 1962, culminating with the Cuban Missile Crisis. It expands on Peggy's rise in the workplace and the marital strife between Don and Betty Draper as Don's infidelities further intrude on his family life. The second season also introduces an unknown acquaintance of Don Draper. Draper is corresponding by letter with this unseen acquaintance in secret.
E1Jul 200849m
It’s Valentine’s Day, and the Sterling Cooper advertising agency is hustling to stay on top of its game and buzzing over the newest office equipment. Don and Duck find themselves at odds over an account. Betty reconnects with an old friend and once again finds herself struggling with car trouble.
E2Aug 200849m
Paul hosts a party at his apartment and introduces someone special to his Sterling Cooper colleagues. Peggy visits her family for dinner. Despite a conflict of interest, the Sterling Cooper agency aggressively pursues an airline account and Duck attempts to appeal to the client using an unorthodox approach.
E3Aug 200847m
Trouble arises on the set of a commercial; Harry tries to gather support for a controversial sponsorship; Betty and Don try to appease a client with a friendly dinner.
E4Aug 200848m
Peggy's family hosts a lunch for their church's new priest; Don and Betty enjoy a weekend together; Pete and Ken take a client out to lunch; the staff works to prepare for a last minute pitch meeting.
E5Aug 200849m
Don has to deal with issues between a TV comedian and his wife; Joan finds Don the perfect secretary.
E6Aug 200848m
Don and Duck try to make peace; Peggy tries to get into the executive's after-hours meetings; Duck deals with a family visit.
E7Sept 200848m
Don buys a new car; Pete, Harry and Ken strategize to attract new business; Don's secretary makes a grave error; Cooper has a new piece of art in his office.
E8Sept 200849m
Peggy contributes on a church project; Duck and Don try to create market appeal for a foreign beer brand; Harry recruits assistance to help with the workload in his department.
E9Sept 200849m
Freddy Rumsen disappoints his team during a pitch. Pete finds an opportunity at the office to exploit while Don proves his loyalty to an old friend. Betty finds a welcome distraction in Sara Beth.
E10Oct 200848m
Betty visits her father; Paul's girlfriend tries to convince him to prioritize his duties; Pete's mother disapproves of his and Trudy's idea.
E11Oct 200848m
Don makes some new friends on his trip to Los Angeles; Peggy looks for romance; Duck ponders the future of Sterling Cooper.
E12Oct 200848m
Don meets up with an old friend; Pete's personal life presents problems; Joan brings her boyfriend to the office.
E13Oct 200848m
The office scrambles without Don; Betty learns some disconcerting news.