New York City, 1960s. In the ego-driven Golden Age of advertising, everyone is selling something and nothing is what it seems.

Don continues to conceal his complicated personal life, even in the face of Roger's invitation to open up.

Don Draper is shaken when his past life comes back to haunt him. After his picture appears in a local newspaper, Adam Whitman, a man who claims to be his younger brother, approaches him. Don, or Dick as his brother knows him, initially denies everything but in the end admits to having taken on a new name. He refuses however to have anything to do with him and tries to buy his silence. When one of the ad men gets a short story published, Pete Campbell is frustrated that his own stories have yet to see the light of day. When his wife approaches an old beau to see if he will publish the stories, he has an interesting proposition for her.

The Agency is looking to land an advertising contract to promote tourism to Israel. Don and his team try to come up with a theme but know so little about the country that they're stumped. So Don calls Rachel Menken to see if she has any ideas. Roger Sterling is getting tired of sneaking around with Joan Holloway and suggests she should get her own apartment but she knows better. Peggy comes up with an advertising concept during a testing session for a new line of lipsticks and she's subsequently asked to write copy.

When Don invites Roger home for dinner, too much alcohol fuels repercussions between Don and Betty and between Don and Roger. Joan puts Roger off for the weekend, spending time with her roommate Carol instead. Pete exchanges a wedding gift for a rifle, and then shares a hunting fantasy with Peggy. Bertram Cooper arranges for the Nixon campaign to meet with him, Roger, Don, and Pete.

Pete Campbell and Peggy Olson start an office romance. Peggy's copy for the lipstick account goes over well and the men in the firm congratulate her. A new telephone receptionist, Lois Saddler, takes a liking to Salvatore Romano but his own interests seem to lie elsewhere. Don Draper gets an unexpected bonus from Bert Cooper and wants to take Midge on a surprise trip to Paris. She seems too involved with her beatnik friends however. Don reflects on his unhappy childhood and in flashbacks he reveals some life lessons he learned early on when a hobo spent the day working on the family farm in exchange for a meal.

Don makes a bold, desperate move to save Sterling Cooper Draper Pryce, but the other partners are furious with his actions. Meanwhile, Sally's psychiatrist suggests that she is improving, but Betty is skeptical.