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Lou later becomes upset when the partners allow Don to come back to work in the creative department and report to him, possibly recognizing how much better Don is at the job than he is. Stan is one of the few members of the SCDP creative department who survives the staff cuts. Following an encounter with Beth's husband, Pete desires a pied-à-terre in Manhattan that he can use for affairs, though he tells Trudy he needs it for late nights at work. The choice to be truthful makes an impact on Sally and she begins to forgive her father for his transgressions by the beginning of Season 7. He subtly indicates to Peggy that he would hear her confession if she wished, stating that "no sin is too great for God." He flies to New York on a whim and continues pursuing Joan.

When Helen confronts Betty at the grocery store, Betty slaps her across the face. Ted and Don commiserate at a bar over their very low chances of winning the Chevy account, primarily due to the small size of their respective firms. When Pete voices concerns to Bob that the nurse Bob recommended, Manolo Colon, may be sexually abusing his mother and taking advantage of her dementia, Bob says Manolo doesn't date women and then hints heavily at his own romantic feelings for Pete, which Pete, repulsed, rejects. [18] Don begins to see Connie as something of a father figure whom Don seeks to impress, but Connie is ultimately unsatisfied with Don's work. Duck returns in the penultimate episode of Season 7 "The Milk and Honey Route" to successfully recruit Pete to Learjet.

He first appears in the sixth episode of Season 5, "Far Away Places". Cutler is a veteran of the Army Air Force and mentions that he participated in the Bombing of Dresden in February, 1945. Joyce Ramsay (Zosia Mamet) works as an assistant photo editor at Life magazine in the Time-Life Building, where Sterling Cooper Draper Pryce is located.

Pete had not realized this because no one at SCDP had ever bothered to check any of Bob's references. Ken's happy-go-lucky attitude begins to fade, and the number of things he has to do for work that he does not like, increase. In season 6, he and Rolo, a friend from Hotchkiss, bring alcohol when visiting Sally and her student hosts at Miss Porter's School. Dr. Greg Harris (Samuel Page) is Joan's ex-husband, as of Season 5.

Pete, distraught with the idea that Ken would be working for SCDP again, got confirmation from Lane Pryce that they indeed intended on bringing Ken to the firm. Aged 9 in Season 1 (1960), he develops a crush on Betty. When Don is placed on indefinite leave of absence from Sterling Cooper & Partners at the end of Season 6, Lou is brought in as a replacement creative director-for-hire on a two-year contract. In his tape recordings for his autobiography, Roger reveals he'd had an affair with Miss Blankenship when he was a very young man at the firm, which caused a rift between Cooper and himself. Born to an upperclass British family, she's stylish and polite, though a bit snobbish and self-involved.

Draper is unhappy with hearing a woman talk to him assertively at the business table. In light of Ken's new position, Roger and Pete attempt to mend fences with him, especially when SC&P seeks to retain some autonomy from McCann-Erickson by proposing to move operations to Los Angeles. In Season 7, Margaret abandons Brooks and their son Ellery to live in a commune in upstate New York. After sending Don to numerous Hilton properties throughout the country, Connie flies Don to meet him at the Hilton property in Rome, with Betty joining at the last minute to help put the property through its paces.
Joey and Peggy seem to enjoy working together, reenacting the "John and Marsha" comedy skit[14] in a workroom and laughing. By Season 4, a more confident and slimmer, if smarmier, Harry shows great progress at work, as he is often seen making deals with television networks on the new agency's behalf. In Season 3, Gloria is not seen, but Betty's brother William discovers that Gloria, unable to deal with Gene's deteriorating condition and overall difficult demeanor, has left him and moved to Boca Raton. Don's first encounter with Rachel, in the pilot, is at a meeting where he pitches the idea of using coupons to attract more customers to the store. When Joan refuses to choose between her career and her relationship with him, he ends their relationship without saying goodbye. Andrew "Bud" Campbell, Jr. (Rich Hutchman) and Judy (Miranda Lilley) are Pete's elder brother and sister-in-law. Harry has once again failed to read a situation properly, and his boastful posturing thus results in him losing an enormous amount of money when McCann Erickson buys Sterling Cooper, where even the 5% stake Joan had is worth at least $1,500,000. She is last seen in the Season 7 episode "Lost Horizon", telling Roger that she has found another job as a secretary at a publishing house, and won't be moving with them to McCann, and that "some people don't feel welcome in advertising". Realizing this on the train back, she has no choice but to go to Don's work and ask him for a ride. Based on a comment made by Joan, Bob assists Pete Campbell in getting an experienced nurse for his now-ailing mother. [10] Feldman ultimately kept the prop. Marie and Roger also resume their affair, which Megan learns of accidentally. He, in turn, seems bitter toward his wife, accusing her of infidelity; he is much closer to Megan than to Marie and urges Megan to pursue her dreams. He tries unsuccessfully to poach Pete and Peggy from Sterling Cooper, which leads to a sexual relationship with Peggy. His politics come to a head when, during an argument with partner Jim Cutler, Ginsberg denounces Dow Chemical for the use of its Napalm in Vietnam. One of his party accidentally dropped a hint that he may be working with SCDP soon. She died on the 37th floor of a skyscraper.

She was originally Draper's secretary, but showed surprising talent and initiative, including a knack—similar to Draper's—for understanding the consumer's mind. She is not seen again and is the last person with whom Don has an affair while married to Betty. Ken calls Cynthia "his life" and does not want to use her or his future father-in-law to get business, claiming in Season 4 that he does not want to be like Pete Campbell. He is engaged to Cynthia Baxter, whom he met while trying to get published. She is well regarded and remains professional and unfazed by Pete's frequent angry outbursts and verbal abuse, which are often directed toward her. Don tricks Ted into making an expensive presentation to Honda executives, which backfires on Ted as he violates Honda's presentation rules of no finished work or commercials. He returns in Season 4, working for his father at a Christmas tree lot, where he encounters Sally Draper and fixates on her as a replacement for Betty, bonding with her over their now-shared experience as children in divorced families. Cooper starts going about his duties with more vigor and enjoyment than he has for the past two seasons, and more effectively than Roger and Don, the other major partners. Cooper's younger sister, Alice, is a silent partner at Sterling Cooper and invested in the company when it was just getting started.
During Season 3, it is revealed Duck, apparently sober once more, is now working at Grey, another New York agency. Dorothy "Dot" Dyckman Campbell (Channing Chase) is Pete's somewhat detached mother who comes from a prominent New York City family. In the Season 4 episode "Chinese Wall", she indicates to Don an interest in advertising, and one night, while discussing work, Megan initiates a sexual encounter with Don on his office couch. She is deceased and appears in Don/Dick's flashbacks. Bert, at the meeting of Harry's outburst, assures Joan that will never happen. He is called by a GM executive (Matthew Glave) asking to be bailed out of jail, having been arrested for offering to fellate an undercover police officer. Cynthia appears as a background character in several episodes of Season 5. In the Season 4 finale, Don hires Megan to babysit his children on a trip to California, when his planned childcare falls through at the last moment. Caroline (Beth Hall) is Roger Sterling's longtime secretary, first appearing in Season 4's "Christmas Comes But Once a Year". Rachel confidently replies that business is a thrill and adds that she's never been in love. She stops him and urges him to go to his wife. She has a noticeable limp as a result of polio and a sister named Patty (Susan Leslie), in whom the real Don Draper was interested before he married Anna.

In Season 3, Trudy and Pete have a closer relationship than they did before and seem to work together as a team, though Pete blackmails a neighbor's au pair into having sex with him when Trudy is away on her summer vacation with her parents. But Betty refuses to do so, just as she refuses to quit smoking or to quit her plans of studying psychology at a university as long as she is physically able.

Although neither firm ultimately wins the account, a betrayed Stan gives Peggy the finger at a bar. As a favor to Jane, Roger forces Don to hire her cousin Danny Siegel, despite Danny's unimpressive portfolio and job interview. He has a complicated love/hate relationship with his son, whom he dominates, sometimes by physically violent means, in order to make him "take action and sort his problems" so as to "put his house in order". Later, Betty uses a political pretext to call him to ask if he can use his influence to save a local reservoir, and they quickly develop a deeper connection. He becomes repeatedly confused, believing himself to be back in the army or in the midst of prohibition; he mistakes his daughter Betty for his wife and fondles her. Shirley is originally on Peggy's desk at the beginning of Season 7, but after confusion with Peggy over Valentine's Day flowers sent to Shirley by her fiancé, Peggy demands that Joan move her. Allison (Alexa Alemanni) was Don Draper's secretary, first at Sterling Cooper and later at Sterling Cooper Draper Pryce. Megan later reveals to Don that she had been pregnant and miscarried. Draper is the series' protagonist, and more storylines focus on him than on other characters. Bobbie appears to enjoy the dominating treatment, and quickly signals her husband to apologize. Shortly afterward, at her dorm room, Sally goes against orders and reads the letter anyway. After Jimmy insults the wife of Utz's owner about her weight, Don has to intercede and ends up meeting Bobbie, who shrugs off her husband's behavior.

However, in Season 5, it is revealed that Glen still speaks to Sally regularly on the telephone from his dorm at the Hotchkiss School, even going so far as to meet clandestinely in New York. She is very well liked by nearly everyone at SCDP and is extremely loyal to Roger, being apparently close enough to him that she is able to speak her mind to him when she feels he is out of line. She uses that to her advantage by confiding in Dr. Wayne her anger at Don's infidelity, knowing that the doctor will report the session to Don. Later, Helen remarries and sends Glen to a boarding school at her new husband's request. Garner, in Season 4, invites himself to the SCDP 1964 Christmas party, forcing the company to overstep its tight budget to make the party a grander affair for their most important client. Lou Avery (Allan Havey) is first introduced in Season 6 as a creative executive at rival agency Dancer Fitzgerald Sample, competing with Don Draper and Roger Sterling for the Chevrolet account. He tells Betty that he is there to rescue her. Paul expresses gratitude and feels Harry is a true friend, when in fact Harry's lies and desire to get Paul away from him are evidence of him simply not wanting to deal with Paul. Initially unwilling to associate with Adam, Don agrees to meet him for lunch and later visits him at the cheap single room occupancy rooming house where Adam lives. His behavior and manners continue to be erratic and begin to deteriorate throughout the season, culminating in a psychotic breakdown brought on by the installation of an IBM computer in the old creative breakroom in "The Runaways". However, while at a café, she leaves her purse behind.

Don then attempts to reach Adam, and finds out about his suicide.

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