It’s the lead-up to the silly season and the team at the agency grows with new staff added into the mix. There’s also a new client to boost billings when Fred Rumsen shows up offering the agency a $2 million account for Pond’s Cold Cream. But there’s a catch – he wants a job at the agency in return and Pete, his nemesis, must not handle the account.

Meanwhile, Don relies on Allison to shop for the kids’ Christmas presents, promising her a bonus for all of her hard work. True to his word, Allison receives an unexpected ‘perk’ of her role when Don calls drunk – and amorous – unable to find the keys to his flat.

To spice things up in the office, Roger decides to take the Christmas party up a notch when he invites Lee Garner Jr. of Lucky Strike. Roger instructs Joan to change the party's rating "from convalescent home to Roman orgy".
And young Sally battles with the effects of her parent’s divorce. She tells her friend, Glen, that she hates her home and keeps expecting to see her Dad there. Glen takes it upon himself to retaliate for Sally by breaking into the family home.

It’s all work - and a bit of play - for the folk at Sterling Cooper Draper Pryce. Don and Roger tag team Lucky Strike’s Lee Garner Jr. to placate him about new restrictions on cigarette advertising, and then on how much the agency is charging him for their services.
Meanwhile, Pete gets a mix of good and bad news in his business and personal lives. Will he stand up to his father-in-law and land the lucrative Vicks cough syrup account?
Peggy gets to test her ‘indulge yourself’ concept for Pond’s with a focus group of secretaries. During the session, things get uncomfortable when Allison tells a few home truths as Don, Freddy and Peggy watch from behind a two-way mirror.
Later, Peggy meets Joyce, an assistant photo editor at Life magazine, and joins her at a nudes photographer’s party that’s full of surprises. And Don gets a new secretary, this time with little chance that he’ll sleep with her…

Don and Peggy interview an aspiring copywriter, Danny, who name-drops Roger and fires off a round of unimpressive tagline ideas. It doesn’t look like he’s in line for a job, until Roger reveals Danny is his wife’s cousin…

After the lacklustre interview, Peggy boasts to Don about her contribution to the Glo-Coat commercial, confident that her spot will win the coveted Clio Award. Her smug mood soon sours when she discovers that Joan will be attending the glittering awards to charm prospective clients. Meanwhile, Peggy faces a weekend cooped up in a hotel room working with Stan.

Before the ceremony, Don and Roger prop up the bar at the Waldorf-Astoria where a stray comment from one of Ken’s clients makes Pete believe the two agencies will be merging. Don is preoccupied with a fellow lady guest who ends up in his bed.

The morning after, Don wakes beside a different woman. Hungover, Don answers a phone call from an angry Betty – he missed a play date with the kids.

With his mind a jumble of thoughts, Don starts a journal to try to regain control of his life. Meanwhile, at work, Joan is the subject of Joey’s inappropriate behaviour, which is dismissed by Don as boys being boys.

Betty bans Don from spending time with the kids during the coming weekend as it’s Gene’s birthday. So Don distracts himself by focusing on the Mountain Dew campaign and by taking Bethany out to dinner.

On their date, they bump into Betty and Henry who are entertaining a political aide at the same fancy restaurant. Betty can’t conceal her irritation – or is it jealousy? – when Henry interrupts Don and Bethany’s dinner to say hello.

Then it’s Henry’s turn to be jealous when Betty admits Don is the only man she’s been with… How will he cope when Don turns up, uninvited, to Gene’s birthday party?

Joan has some shocking news for Roger, who also learns on the same day that Lucky Strike is pulling their lucrative account from the agency. Meanwhile, Don’s identity risks being exposed after a routine security clearance investigation for North American Aviation. Will Don be found out before Pete can cut the account loose?

Lane’s father, Robert Pryce, arrives in New York to escort his son back to London. Lane rejects the idea, and takes the opportunity to introduce his father to his love, a black Playboy Bunny named Toni. Pryce Senior is far from impressed…

Shaken by the investigation, Don directs his accountant to establish trust funds for his children and to give access to Betty. Growing physically sick over the ordeal, he later suffers a panic attack when he spots two suited men in his building’s hallway.

And Roger once again faces his mortality when going through his Rolodex calling old contacts, when he discovers that one of them has died.

To keep the agency going, Don, Roger and Cooper will each need to
cough up $100,000, while Lane and Pete must contribute $50,000 each.
Over in Ossining, Sally secretly meets up with Glen who has helped coach her to
kiss up to Betty.

Meanwhile Dr Edna congratulates Sally for learning to control her
temper and suggests they meet once a week – which Betty rejects.
Pete struggles to find the $50,000 to keep his place at the agency, with Trudy
forbidding him to use their cash to prop up the agency. At home, Don comes up
with his own unique way to save the agency, but will it work or make things much,
much worse?

And, with drastic staff cuts needed, who will survive the chop?