Mad Men Part 3: Breaking the Chains of Expectation

Mad Men main characters lined up

The second and third seasons of Mad Men illustrated in great detail how the characters in the series were confined by either their gender, sexual orientation, or place in the world. Their confinement dictated their position in their homes, their companies, and often, within themselves. Mad Men pulled audiences into the stifling 1960’s, an era where societal norms and expectations governed the behavior and understanding of the self of anyone who happened to be born into that time period. The fourth season of Mad Men, perhaps the most energetic and electric of the series, picks up in the mid-60’s and begins with many of the characters trajectories that will show them breaking away from their socially inflicted internment and embracing their true selves. Both the fourth and fifth seasons of the series detail the various ways in which each character breaks away from that which held them back, as illustrated in the previous two seasons. Following each character through the brazen fourth and fifth seasons reveals the individual ways in which they decided to break free from their repressive positions both in the outside world and within themselves.Don Draper at an interview

Don Draper

The first words we hear opening the fourth season of Mad Men are “Who is Don Draper?” The question is one that the audience can’t even answer yet, and we’ve been intimately following him for three seasons by this point. Don is continually reacting to life’s curveballs in unforeseeable ways and believes that the best way to escape a situation he can no longer live with is to reinvent himself. Fresh off his divorce and the decision to break away from Sterling Cooper and reinvent the agency he and few that he brought with him didn’t want to leave behind shows Don at his most reinvented. In a new, modern office building with an impressive staff, we can see immediately that the agency has come a long way from the hotel room in which we left them at the close of the second season. Don is living alone for the first time, in an apartment with a housekeeper and spending time with his children on the weekends when they are dropped off with him. Don is more responsible than we’ve ever seen him and seems to be adapting well to his new living situation. Only casually dating, Don spends most of his time working and enjoying the most meaningful time with his children that he probably ever has in their entire lives.

After giving a tight-lipped interview to a reporter determined to let his work speak for him, Don learns that this approach won’t help his fledgling agency attract more prominent and diverse clients, or even keep the ones they have. When a restless Don calls Bert Cooper’s contact at The Wall Street Journal to give a bold interview where Don blends excitement, intrigue, and a little mystery, he proves he is done playing it safe and is ready to be the ad man he once was. This interview arc from the third season’s opener illustrates Don breaking out of the mold that he was previously happy to fill, and taking a more active role in deciding the direction of the agency of which he is a partner. For the first time, we see a Don Draper who is willing to adapt to both the changing times and the changing agency he helped found, as opposed to the rigid version of himself who expected an entire office to bend around him. The mood of the whole agency, the newly founded Sterling Cooper Draper Pryce, (SCDP) has shifted, and this small agency that could, has adopted a renegade attitude taking big risks in hopes of even bigger rewards. At a time when the world was on the cusp of significant change, the employees of SCDP are breaking themselves down to build themselves anew in ways that suit how they wish to be rather than what society envisions them to be. The company’s lack of financial security and living their working lives consistently on the brink of collapse has removed all the comforts of their formerly well-established agency, resulting in the dawn of a forward-thinking group of creatives intent on making their mark in the world.

The displacement from one’s comfort zone is a way to see what someone is capable of when the stakes are high, often bringing out the most revealing personality traits of a person. Surprisingly, the booting of Don from his comfort zone has resulted in him spending more time at work and taking his time at the office more seriously than we have yet seen. Don no longer sleeps through his mornings on his office couch or leaves for his sexual liaisons over his lunch hour. Don still spends time with women and catches the eye of those around him, most prevalently in season 4, Dr. Faye Miller, a strategist for a consumer-research company offering consulting services to SCDP. He is slower at entering into any relationship with Dr. Miller than he has been with any other woman we see him with, but has Don turned over a new leaf or has he shifted his desire from women to alcohol? Everyone around Don can recognize that he is an alcoholic and wholly dependent upon his next fix. Don is no longer the functioning alcoholic we met in the first two seasons, part of breaking away from that which stifles him included his shift in focus to overindulgence on alcohol. No longer recognizing what he asks of others, Don demands more time than ever from those that his position presides over.

On an especially lonely night, Don arrives home realizing that he has left his keys in his office and calls his secretary requesting that she bring them, out of her way, to his apartment. After sleeping with her before telling her the next day that it was a mistake and paying her off with a bonus, it is clear to see that Don has ceased to think of others, instead only caring about himself and satisfying his drunken whims. His indifference to her eventually causes her to quit but not before throwing an office decoration at a tone-deaf Don who responded to her request of a letter of recommendation by telling her to write one that he could sign. His marriage to Betty confined him, but also clearly offered enough comfort and direction to keep him from taking advantage of those whose position prevented them from standing up to Don.

Don kisses Anna's hand at the dinner table

Don takes another business trip to California where he immediately visits Anna’s house. While there he meets Anna Draper’s niece, Stephanie, and it is initially unclear where Don intends to take the relationship. Their sexual chemistry is apparent, but so a reluctance on Don’s part to begin a courtship with someone so much younger than him. If Don were to date someone significantly his junior, not only would he be fulfilling the stereotype of the divorced ad man, but he would also be thrust into confronting his issues with the younger generation. Don also seems initially reluctant to enter a relationship at all, as it would mean entering another area of confinement that Don is so intent on preventing. Instead, Don and the college student talk, fascinated by their generational differences. While in California, Don is as open and relaxed as we’ve seen him in season four and he admits to Anna that he believes Betty left him because of his past rather than the lies. His history and the modest financial state of his birth family are matters from which Don cannot escape no matter many times he attempts to reinvent himself.

Don also learns during his visit that Anna has cancer and not long to live, facts that Anna’s doctor has thought best to be hidden from her. Don says a final goodbye, unbeknownst to Anna, as he is forced to face another ending and subsequent release from his life. In a way, Anna represented yet another source of confinement that Don was now released from, but this confinement was the only one in Don’s life that he embraced. Deciding to end his California trip early after learning the devastating news, Don returns to New York and is shocked to find anyone in the office over the winter holidays. Lane and Don bond, and begin to understand each other in a more human way than they ever had before. Don talks to Lane about breaking from the expectations of society and others after Lane reveals that his wife has left him. Don lets on through this exchange with Lane how astutely aware he is of the societal confinement imposed upon him and others, and the limitations of expectations.
Faye straightens Don's tie

Don admits his struggles of co-parenting to Dr. Miller after a verbal altercation with Betty was provoked by Sally cutting her hair while she was in Don’s care after he left her with a neighbor so he could go on a date. His work life is as directionless and uninspired as his domestic life, and we see Don giving uninspired pitches and unable to secure clients for the first time in the series. After winning an advertising award for his Glo-Coat ad, Don rides the tidal wave of validation into the office where a pitch with LIFE cereal is taking place and decides to attempt to bring his signature brand of flair to the pitch.

The energy of season four proves its increased electricity when Don embarks on a plan to bankrupt Ted Chaough of the rival agency Cutler, Gleason, and Chaough. Ted has been taunting Don throughout the season, even showing up to accost him at a restaurant while on a date. When they both have an opportunity at a Honda pitch with clear rules laid out, Don lets Ted’s agency think they are breaking the rules and producing a television commercial, knowing that CCC can’t afford this. The bold plan not only exposes CCC as rule-breakers, almost certainly excluding them from landing Honda but also allows SCDP to be seen as the morally superior agency that refuses to work with those who blatantly dismiss protocol, possibly gaining the most significant account they may ever have. While throwing out a dozen taglines seeing if anything sticks, a far cry from Don’s usually well thought out yet open to improvisation style, he inadvertently steals a line from an interviewee he previously decided not to hire. Of course, this is the Line that LIFE chooses to use forcing Peggy to remind Don of the origin of the line making him realize he’ll have to hire the discarded applicant, a cousin of Roger’s wife, Jane. This slip exposes Don’s drinking as a severe hindrance to both his work and the company.

Don and Peggy in the office

There is another moment in the fourth season of Mad Men in which Don exposes his special relationship with Peggy. After receiving an urgent message from California, Don drinks himself into a stupor while working on pitches for accounts he’s not even on in an attempt to avoid making the call to California and learning of Anna’s death. He coerces Peggy to stay even after she reveals to him that it is her birthday and she had dinner plans with her boyfriend. Don is so unhappy that he doesn’t mind sabotaging the happiness of others. After an argument in which Peggy calls Don out for his selfishness, the two, sulk independently before Don takes Peggy out for dinner and drinks to make up for her missing her birthday festivities. Don drinks too much and gets sick, then allows his emotions to overflow in front of Peggy. After returning the call to California and learning of Anna’s death. Don’s willingness to permit Peggy to see him at his weakest most vulnerable moments proves the one he shares with Peggy is a special relationship for Don. Their interactions transcend both their titles and their gender roles. There is no one else in the series that we have seen Don allow himself to be helpless in front of, nor have we seen Peggy allow herself to be emotional in front of anyone else in the office for fear of being taken less seriously as a woman. When Don tells Peggy that the only person to ever truly know him passed away, Peggy assures him that this isn’t true, a nod to the audience that Peggy also knows the real Don even if he doesn’t always realize that.

Toward the end of season four, Don takes a reflective stance on what his life has become and begins journaling and seems intent to work on his drinking. We see Don denying drinks for the first time all series and attempting a healthy mature relationship with Dr. Miller, a female version of Don who has reinvented herself after running from her past. Just as things seem to be improving for Don, Sally shows up at his office unexpectedly. Don calls Betty who says Don needs to handle his daughter’s recent rebellion, as she is at her wit’s end. Don farms his parenting responsibilities out on others, angering Dr. Miller. After running out into the office exposing Don’s domestic shortcomings, Megan comforts both Sally and Don making herself stand out for the first time since her introduction in the series. The company is delivered a devastating blow when it is revealed that Lucky Strike has left SCDP, along with many other smaller accounts threatening the future of SCDP. As Megan takes a more active role in monitoring Don’s drinking and babysitting his children, the two become closer, and a relationship begins.

Inspired by Peggy’s reminder to him to change the conversation when he doesn’t like what’s being said about him, and knowing that saving SCDP is going to require a big move, Don writes a letter that appears in The New York Times, stating that he and his company will no longer represent the tobacco industry. Don and Megan’s whirlwind romance stuns the office and upsets Roger when their marriage is announced. Their marriage forces Don to face his apprehensions towards the younger generation. Don has felt hemmed in by his reluctance to change and adapt to what the incoming generation means to him and those of his age. When Megan throws a surprise party complete with an overly sexualized song and dance in front of all the guests, their age difference is on full display. The relationship that was supposed to make Don feel young and fresh instead made him feel older and pathetic. Don is also dealing with his age as he has suddenly become the boss that younger ad agents throw dinner parties to impress, unlike the dinner he attended in hopes of impressing Roger in the opening season. Both his new marriage and his advancement in years force Don to face maturation as the differences between generations becomes more apparent. When Megan admits to Don that she wants to resume acting, it is even more present that their differences are so extreme. The moment of realization for the audience is when we realize that Megan’s trajectory is not that different from Betty’s. Betty was a former model, which she gave up for Don, who always accused her of being childish. Megan is much younger than Don and also wishes to go back to her more artistic aspirations, goals Don is incapable of understanding. These generational differences and how Don is threatened by those younger than him wreak havoc in his marriage and challenge his expectation of what a wife is supposed to be, a role that Megan does not want to fill as Don has imagined it.

Lane reads a note while sitting on the office sofa, Don stands in front of him with a bottle of whiskey

When Bert Cooper approaches Don regarding a check he has found written to Lane and signed by Don, Don takes the flack for what Bert thinks is a signal that he waffled against the company’s decision not to grant Christmas bonuses, but Don had nothing to do with this and immediately goes to Lane. Lane admits that he wrote the check to himself in what was supposed to be a short-term loan until the bonus checks went out before they decided against giving out bonus checks. Lane got himself into arrears and owed taxes to England while he was living in New York. Despite Lane having noble interests at heart, he still embezzled money losing Don’s trust. No longer able to believe that Lane will execute the company’s finances responsibly, Don fires him. Without a job to keep Lane in New York, he will be forced to return to his former life in England and leave the country he has fully adopted as his own. Lane enjoys the life he has reinvented for himself in America and believes it to be better than the one he formerly occupied and will do anything to keep it. When he realizes he will no longer have a choice, Lane decides to escape the impending confinement by killing himself. When Lane’s body is discovered in his office, with the resignation letter in his pocket that Don asked for, Don suddenly feels responsible for two suicides. After Lane’s death, Don begins to have visions of Adam everywhere he goes.

Don broke free from the confinement he felt when married to Betty, in a house in which he didn’t feel as though he belonged and with the family with whom he felt like an outsider. Breaking free from one source of constraint only led to Don falling into another, as he quickly married again to a woman with many of the same attributes that he disliked about in Betty. Don also found himself unable to run from the implications of his age in the fourth and fifth season of Mad Men. His marriage to a young free-spirited woman with artistic ambitions made clear to Don how firmly he was entrenched in his age, whether he wanted to be or not. Most aspects of life can be rewritten, but the year you were born cannot, a fact Don understood fully throughout these two seasons.
Peggy Olsen in the ladies room

Peggy Olson

Peggy proves her immeasurable worth to SCDP in the premiere of season 4 when she saves the company by learning that an account is planning on leaving. At the stage of her discovery, the loss of any account would mean the downfall of SCDP, so Peggy’s instance of keen attention deserves to be recognized for some of what makes her so vital to the company, yet is often overlooked. When a sober Freddy Rumsen reemerges at the office hoping for a second chance with the company, no one is happier to see him than Peggy, as he is one of the few people with whom she does not feel the intense need to prove herself. Unlike Don, Peggy cannot break away from the one area that confines her the most, her sex, so having someone else around that doesn’t see her as less of a person because she is a woman is a welcome addition to the office. Freddy isn’t back for long before reminding Peggy about his old world gender expectations proving the multifaceted human nature of people within changing times. It is also with Freddy that Peggy has a tender moment in which she discovers how she feels about her relationship.

Freddy suggests to Peggy that she shouldn’t have sex with her boyfriend if she intends to marry him. Peggy has sex with him for the first time that very night, when she accepts that she does not wish to marry him and has been unhappy in her relationship for a while and is still trying to conform to social expectations. Peggy sends flowers to Joan, and it is seeing women like her who appear to be happy in their marriages, making Peggy question whether or not she should make the best of her situation and join the ranks of wives among the office. Peggy is also shown still having to deal with the assumption from those at SCDP that she achieved her position in the office by having a sexual relationship with Don. When Don’s secretary opens up to Peggy about her feelings towards Don under the assumption that Peggy also has feelings for him, Peggy unleashes her pent-up frustrations. In addition to the presumptions of those in the office, Peggy also struggles with the new personalities brought aboard. An openly sexist and misogynistic creative director rubs Peggy the wrong way with his consistent arrogant and rude behaviors and his lack of office etiquette. The feeling is mutual, and Don sequesters them to a hotel room over a weekend to work out their differences and complete the pitch they had been assigned to work on together. After making many sexist remarks implying Peggy to be a prude, Peggy suggests that the two do their work in the nude to prove that Stan is all talk. The two conclude the weekend still in a state of dislike of the other but respecting each other a little bit more than when they started. Peggy feels forced to take action like this as a means to prove herself. Peggy’s religion and status as an unmarried woman in the mid-60’s are areas of confinement in which she feels entrapped. She feels as though she must prove herself in bold ways to the men with whom she works.

Season four proves that Peggy is perhaps the only character who enjoys a social life that is entirely separate from the office. Peggy works hard, one of the few characters we consistently see arriving early and leaving late, but when she goes, she leaves everything there and engages with people outside of work with whom she doesn’t spend time with at the office. The fourth season of the series shows Peggy’s social life expanding when she meets a magazine photographer who invites her to a beatnik party, Peggy begins to meet a host of socially conscious individuals whom she starts spending most of her time with outside of work. Peggy even meets someone who is more of what she is looking for in a life mate, rather than her current boyfriend who only seems to care about impressing Peggy’s family. Peggy’s new friends and her budding relationship with the journalist open her eyes up to the social unrest taking place outside of Madison Avenue, forcing herself to take a side abandoning the ethical middle ground she typically occupies.
Peggy and her friend go to a club

On the night of her birthday when a drunken Don all but demands that she stay at the office, Peggy learns that her boyfriend had planned a surprise dinner for her with her family, the exact thing Peggy didn’t want. She wanted a romantic evening with her boyfriend, not a chance for him to prove to her mother and sister that he was marriage material. When Peggy calls the restaurant to tell her boyfriend that she won’t be able to make it, her mother belittles her, and her boyfriend, upset at being stood up, breaks up with her over the phone. An upset Peggy has it out with Don, sharing everything that has been bothering her, about Don taking credit for her Glo-Coat idea that he was awarded for, and about being harder on her than the other creatives. Don accuses Peggy of thinking of everything as an opportunity, to a degree, she has to, as a woman in a predominately male industry. All Peggy is really after is a sense of validation and mutual respect from Don and for someone to recognize her unique contributions to the company. After their argument, Don and Peggy makeup and they reveal even more about themselves as they only would to each other. Don even takes Peggy to dinner where Peggy reveals that her father died when she was young, and she saw him die, just as a young Don saw his father die. Don also opens up to Peggy about his childhood. The two return to the office where a drunk Duck Phillips comes to take Peggy with him, but she refuses to leave with him, cementing her loyalty to Don. The two fall asleep in the office together before Don awakes to make the call to California where he finds out for sure that Anna has died. Don breaks down in front of Peggy giving a break to the brand of masculinity he is expected to present at all times which confines his spirit.

Peggy and Don passed out drunk in the office together

Peggy lands an account following a lead all on her own, the first new business to come to SCDP since Lucky Strike’s departure, around the same time that Joan is named partner, and the two share a moment as they lament that neither of their achievements is as celebrated company-wide as when the men bring in new accounts. Despite any friction that exists between them, Peggy and Joan share the struggles of what it means to be a woman in the 1960’s. When Don makes Megan a copywriter, as Joan predicted he would, it brings Peggy even more unrest as she was essentially handed a job that Peggy had to scrap for, to make her marriage to Don look more respectable. Despite gaining from her new job title, the reason she was promoted is a sign of sexism toward Megan, as well as a sad statement on the power dynamic of marriage and the workplace. Men and women alike are held to such rigid standards of what it means to be a man or a woman that they have no room to explore what it means to be a person. Peggy feels so slighted by Megan encroaching on her workspace and being given accounts that would otherwise go to Peggy, that she begins to think about going to another agency.

Another relationship significant to Peggy reveals itself in the fifth season of Mad Men. When Peggy sees Ken at a lunch that she assumes is with another agency, she asks him for details and is only satisfied when she learns that the dinner was with a publisher. Ken is still writing while appearing to effortlessly work at SCDP, refusing to give up on his dreams of being a writer. Ken reminds Peggy that his promise to her is still valid and if he ever leaves the agency, he will take her with him. As her relationship with Abe the reporter intensifies, he asks Peggy if she’ll think about the two of them moving in together. This arrangement, as unconventional for the time as it is, is perfect for Peggy as she wants to be in a relationship but is not yet ready to get married. She talks with Joan, whose own marriage struggles have made her see that a wedding isn’t the ideal finish line like she thought it was, who is genuinely happy for her. Joan advises Peggy to do what makes her happy despite what others may think because she is the only one who will have to live her life every day.
Don kisses Peggy's hand as she leaves

Peggy eventually decides that the only way to break free from her confinement is to leave SCDP. She thinks that getting out from under Don’s thumb and forging her path in an agency where people aren’t under the impression that she slept her way to the top, or where she’s given accounts simply because she’s the only female copywriter is the only way people will begin to take her seriously. Peggy has been awakened to a world that she had often ignored, the struggles of those marginalized, and the plight of those that have an even harder time getting anywhere in the world than Peggy does. Her social consciousness and her understanding have developed, and her independence has been cultivated. She is heartbroken to leave Don, the one who gave her a chance, but she feels it necessary to successfully make her portfolio and prove to everyone, including herself, that she can make it on her own using all that she’s learned from him. Peggy consistently attempts to break away from the confinements that entrap her, but never more so than during the fourth and fifth seasons of the series.

Pete Campbell smirking

Pete Campbell

Now that the company they work for is much smaller, with fewer staff members, Pete and Peggy work on accounts together and prove their maturation as co-workers with a history. Freddy’s return to the agency is contingent upon Pete staying away from him and the two never being tasked to work on any accounts together, proving that Pete has made no more friends in the office than he has all series. When an account worth more than Clearasil comes to SCDP, Pete must talk to his father-in-law and tell him that the conflict of interest will prevent his agency from continuing to represent his company. When Pete meets with him to discuss this, his father-in-law lets slip that he knows Trudy is pregnant and wishes to celebrate with Pete. He tells him that he will gift Pete and Trudy $1,000 if their child is a boy and $500, if the child is a girl, which is not only paying him off for finally producing a child as Trudy’s family, has always wanted but some pretty blatant and troubling sexism as well. Pete capitalizes on his father-in-law’s excitement over the baby and his newly cemented position in Trudy’s life to seize more brands under his company’s umbrella demanding that he represent more than just Clearasil. Pete thinks if he can bring more business to SCDP and raise his position within the company, he’ll succeed and be happy.

For Pete, the definition of a successful 60’s ad man means that he must gain more titles and a larger office to prove himself as worthy both at work and at home. Stifled from every direction, Pete is faced with his inadequacies when Henry arranges a lunch with himself, Pete, and Ken Cosgrove. Pete is jealous of Ken’s success, and his ability to climb the ladder at two different agencies. Pete and Ken work out their differences just in time for Ken to be hired back at SCDP. When Roger takes a firm stance against SCDP attempting to represent Honda when Pete wins them a pitch, Pete thinks that Roger’s reluctance is due to his desire to keep Pete from bringing in a lucrative account. Pete is so egotistical that he thinks someone would exist solely to hold him back rather than to recognize Roger’s fear of losing relevance within his own company. Pete is so intent on gaining public leverage that he asserts himself at every opportunity he can. When he brings in Mohawk Airlines, he takes the full credit for it, despite the clear help from Roger, then refuses to give him the account despite his promise to do so. When Ken is given condolences at a dinner party on SCDP’s loss of Lucky Strike, the fact that Roger had withheld from the rest of the agency, he immediately calls Pete to start damage control. Don and Pete’s relationship is still being tested when Pete is blamed by Don when Glo-Coat decides to leave the agency for being distracted over his wife’s labor. When Pete goes to visit his wife in the hospital, he sees Ted Chaough there who offers him a full 1/3 partnership at CCC. The promise of financial and status gains is offered to many as a means to escape that which binds them throughout the series run of Mad Men. Offers for other work are made to many at just the right time when they feel most suffocated by their positions.

Pete Campbell wearing headphones and looking sad

Pete reaches a definite crossroads by the time the fifth season of Mad Men begins. He embodies a sense of unsettled energy as the charade of his life continues. Both in life and professionally, Pete has lived his entire adult life merely checking the boxes of what’s expected of him. He has married, bought a home, had a child, continues to work his way up in his company, and yet he remains unsatisfied. To his surprise, each advancement he makes on the checklist of life doesn’t bring him the happiness he expected and only leaves him restless. Pete is so unfulfilled in his life that he begins looking for things to satisfy him outside of his home. Pete opens up to someone who he shares his daily commute with into the city that his wife has been too distracted by their newborn to take care of herself to Pete’s expectations. Still upset about not living in the city, Pete begins to take driving school to shorten his commute time to work every day, where he immediately starts looking for women with whom he may have an affair. He is emasculated when the woman he planned to go on a date with disregards him when another attractive younger man begins driving school. When the man he shares his commute with opens up to Pete about the affair he’s having and his apartment in the city, things that Pete would love to try as a means of improving his own life. When Pete’s commuting partner’s wife mistakenly drove to the station forgetting that he was staying in the city, she and Pete have sex. Pete is intent on keeping their affair going but soon learns that will be impossible due to her electroshock therapy that will cause her memory to suffer and likely forget who Pete is. Unable to catch a break, the one woman who is willing to enter into an affair with Pete won’t remember who he is days after sleeping with him.

The lowest moment of season five comes when a Jaguar executive promises SCDP a chance at representing their company in exchange for a night with Joan. When Ken hears this he immediately wants to kill the conversation, uncomfortable with the direction it is taking, but Pete keeps the man talking, eager to see what terms would have to be satisfied in order to bring a car company to SCDP finally. Pete is the one to approach Joan in an attempt to convince her to prostitute herself in the hopes of maybe landing Jaguar. Pete also goes to the partners with the conditions from Jaguar. All of the partners initially refuse with Don being so disgusted that he walks away from the conversation. The men think of a way to sweeten the proposition for Joan and consider paying her with a portion of the deal. Lane knows the agency can’t afford this on top of the money he has been embezzling to pay his taxes overseas. He instead urges Joan to request a partnership convincing her that would set her up for the rest of her and her young son’s life.
Lane gives Pete a right hook while Sterling and Don watch on

Pete’s masculinity is questioned in every area of his life. He gets into a physical altercation with Lane at work in which he is bloodied and bruised. His wife has lost all interest in him since their baby was born. He is embarrassed when the company accountant has a higher chance of bringing new business to the agency than he does. Pete embarrasses himself by being unable to fix a leak before a dinner party in his home resulting in water spraying all over his kitchen when his company arrives. In hopes of bringing him down and asserting his dominance over Ken, Pete reveals to Roger that Ken is still writing resulting in Roger accusing Ken of not focusing enough on his job demanding that he give up writing. Pete also spends the entire fifth season giving Roger the runaround and, climbing on others to bring himself to the top. Desperate for true happiness and fulfillment, Pete tries to escape the confinements of his job, his marriage, and his living situation at every opportunity.
Joan Harris in the office

Joan Harris

Back to work, Joan has her own office in the new SCDP building and is doing work for the company that is more respected making Joan feel like a significant member of the agency, giving her a renewed sense of self-worth. Despite the increased responsibility, Joan still struggles as she loses the sense of control she once had over the office. Some of the newer employees of the office don’t understand her unique and critical role and disobey her and undermine her, something that never would have happened when before Joan left the office. As much as she doesn’t want to admit it, this clash with the new creatives who undermine her bothers Joan a great deal, not only because it signals a shift in office dynamics, but also because it means that she is starting to be seen as the matronly figure she always feared becoming. The younger men in the office think of Joan as desperate assuming that to be the reason she dresses the way she does because it is believed that a woman dressing her shape and how she is comfortable is always to gain the approval of the men around her. Her struggles at work cause her to retreat to Greg, happy that someone still finds her desirable.

The audience follows another character to the gynecologist when Joan visits the doctor to discuss quitting her birth control. It is during this appointment that Joan mentions her previous two abortion procedures, worried that they may impact her being able to get pregnant. Joan is breaking free from her sense of confinement by making all of the decisions concerning her body and when she would begin a family. She chose when she would marry and decided when it was best for her to have children. Joan has realized that she did not pick the ideal mate for her in Greg, but despite this fact, has decided that she wants to have children. One night when she cuts herself making dinner, Greg belittles her job and proves how little about her he knows all while trying to mend her wound. Joan discovers that she could never feed Greg’s ego or build-up his fragile sense of masculinity enough to make him care more about being a good husband or father, but that his inadequacies shouldn’t impact Joan getting the child that she has decided she wants.

Joan and Roger are mugged at gunpoint in the street

Joan and Roger’s relationship remains complicated. He flirts with her, and she always declines, their interactions are often cold as Joan continues to pull away from him. Then, other times, she gives in to Roger’s wishes, like what dress she should wear to the holiday party. Finally, in an attempt to apologize for his piggish behavior towards Joan, Roger pays for a manicure/pedicure and massage for Joan. While thanking him, Roger insinuates that he is owed something in return to which Joan scoffs and laments that Roger doesn’t even know how to apologize correctly. After the death of Don’s secretary, someone who Roger knew for most of his life, he is devastated, and Joan takes him out to dinner to comfort him. When they are leaving the restaurant, they are mugged at gunpoint, and the emotional trauma pushes them towards each other for comfort, and they make love. Joan tells Roger that her emotions got the better of her and she will not be resuming that part of their relationship. “I am not a solution to a problem, I am another problem,” Joan tells him, and for the first time, Roger understands that their sexual relationship is truly over. A few weeks later, however, Joan is late on her period and informs Roger that she is pregnant. Initially, Roger and Joan discuss an abortion for which Roger promises to pay. Joan, however, decides to keep the baby and pass it off as Greg’s who has recently been deployed to Vietnam.

While on maternity leave after delivering her baby, the audience can see Joan has a troubled relationship with her overbearing and domineering mother, and that her relationship with Greg is as tense as ever. Eager to get back to work, Joan fears as though she has been replaced, visiting the office to ensure that her place within the company is secure. Lane assures Joan that the office is barely being held together in her absence and the two bond over the thankless jobs they both perform for the company. Joan goes into overdrive attempting to get the house and herself ready for Greg’s first day home after his tour of duty is complete. The joyous homecoming is brief, however, when Joan learns that Greg has voluntarily enlisted for another tour of duty solely to pad his masculinity and feel important, rather than stay home to bond with his family and help take care of his newborn child. The fact that Greg didn’t even discuss his plans with Joan, and then made her think as though he didn’t have a choice in the matter was enough to Joan to not only tell him that she wants him to leave but to also acknowledge to him that he raped her. This realization is a massive break from confinement for Joan, as she opened the season admitting that her primary goal in life was to get married. Her independence and the pride she takes in her work is more than Joan could have previously imagined for herself. Realizing all that was available to her aside from marriage proved a sharp departure from not only what was expected of Joan, but also what she expected of herself.

Greg has Joan served with divorce papers at her office a crass way of invading the only space in which she had complete control. It is the desire to form her own life free from any man needing to take responsibility for her that convince Joan to accept the terms of the Jaguar executive’s commission. Joan knows a stake in the company will be enough for her and her son to live off of, and she won’t need child support from Greg or Roger to sustain herself. This night not only represents a turning point in the series but a defining moment in the character arc of Joan. Joan is choosing to do things in a much more difficult way that she considered before, but on her terms, breaking free from what she expected of herself.
A man puts a diamond necklace on Joan

After Lane’s suicide and the toll his death took on SCDP, Joan convinces the other partners that a change of scenery is in order when the office space above them becomes available. The billings suggest that their stock is rising and they can more than afford the additional rent and the morale boost, and the fresh start free from the reminders of the unexpected death of their colleague and friend garnered by the new space is too attractive an offer for the partners to pass up. This accrument of additional space also signifies SCDP is breaking free from their modest re-start when they rebranded their agency and moved into the new building. The team was still able to grow and expand even after starting anew with only a handful of clients. SCDP is breaking out of their confinement of being looked at as a little agency, and are once again becoming significant players in advertising.
Betty Draper smokes a cigarette at a bar

Betty Francis

The Francis family was onscreen significantly less in the fourth and fifth seasons of Mad Men. Betty had escaped much of what bound her when she divorced Don and made a new life with Francis. She would see, however, that breaking free from the confinement of her life with Don, would lead to new areas of confinement. The first holiday Betty spends with Henry’s family, Thanksgiving brings criticism against Betty from Henry’s mother who offers her commentary against divorce couples. Henry defends Betty, but the reality of her situation and her inability to change facts about her past visibly affects her. Betty also carries on arguments with Don about the pace at which she Henry are looking for another place to live. Betty claims that she is reluctant to move out of the home that she shared with Don because she wants to minimize the changes that the children are experiencing. It seems as though Betty is the one most overwhelmed by the changes, or perhaps, overpowered by a subconscious effort to hang on to her former life with Don. The reluctance of Betty’s to move causes friction between her and Henry, who is walking the tightrope of being a supportive husband and a divorcee himself. There are many times in which Henry understands Don’s perspective and his actions, but when Don is around Henry and Betty are always a united front. Behind closed doors, however, Betty and Henry have many fights regarding her feelings regarding her divorce, and her interactions with Don. Henry seems to wonder many times throughout the fourth and fifth seasons if Betty is the steady presence he thought she was that he craved for his life. While attending a work dinner with Henry, Betty sees Don at the restaurant with a younger girl he is on a date with, and the sight of them together ruin Betty’s entire night. The fight continues into the car where Henry reveals through what he doesn’t say that he is suffocating by Don’s presence.

Living in Don’s home, surrounded by his things, arguing about him with his new wife, there is no escaping Don Draper for Henry. He admits to Betty some of what he is feeling which inspires her to release some of her negative feelings and extend an olive branch to Don, inviting him to baby Gene’s birthday party. This invitation signaled a shift in Betty as she seemed to genuinely be moving on from Don and the pain she endured throughout their marriage finally agreeing with Henry to look for a new house. Don and Betty even share a moment of closure, just the two of them, as Betty moves out before the realtor comes over to list the house. Betty breaks away from her resentment toward Don at the same time that she breaks away from her longing for what they might have been. Often, when a relationship ends, there is a period of introspection where one wonders if things were different along the way would their outcome have been different. Betty had to let go of a lot of pain and resentment that was holding her back in her relationship with her new husband, and break free of the confinement that her first marriage had over her second.
Betty and Don at their house

Betty continues to struggle with her children, feeling her identity defined by her status as a mother. The older Sally gets, the more tension arises between her and Betty. Sally begins talking to Glen again, against Betty’s wishes, as she struggles to believe that a boy and a girl can be friends without a sexual element involved. Sally and Glen’s relationship is strictly platonic, with Glen’s only goal being to provide support to Sally, as a product of divorce himself. Every difficulty that arises with Sally leads to an argument between Betty and Don where Betty lays bare the years of torment and neglect that she endured during their marriage. After Sally masturbates at a friend’s sleepover, Betty informs Don that since he isn’t addressing Sally’s acting out that she will be sending her to therapy. Don’s feelings about treatment were made clear when he hijacked Betty’s therapy and discussed with her therapist what she disclosed in their sessions throughout the first two seasons of the series. We still see Betty more concerned with how society views her than Sally’s well-being. The hostess of the sleepover and her judgments on Betty’s life and critical attitude toward her divorce is what pushes Betty to act to protect her image rather than concern for her daughter. At the first of Sally’s sessions, the therapist can tell that Betty is a wounded woman, and suggests that the two talk each time Sally comes in as a means to provide an outlet of support that Betty would otherwise fail to seek out for herself. After several weeks of therapy, the therapist no longer deems it necessary for Sally to come in as often for sessions to which Betty protests because she doesn’t wish to lose her opportunity to talk to someone. In a cruel callback to the first two seasons in which Betty’s former psychiatrist tells Don that she is like a child, the therapist reminds Betty that she would have to see someone else for regular sessions because she is a child psychologist.

After constant struggles with Glen and Sally meeting behind her back, Betty forbade Glen from their home. The day of their move, however, Glen stops by while Betty is out begging Carla to let him say goodbye to Sally, which she eventually reluctantly allows. Unfortunately, Betty returns home while Glen is still there and becomes so enraged with Carla for disobeying her that she fires her on the spot. She later fights with Henry over the incident when he learns from Carla that Betty has refused to write her a letter of recommendation. The firing of Carla just as Betty is moving out of her and Don’s marital house illustrates that she has broken free from every tangible reminder of her marriage to Don. In the new home, without his belongings taking up space and with a new housekeeper, Betty is free to truly begin again without any material tether to Don or their marriage. Betty is breaking free from the former life that she lived with Don and genuinely starting her new life with Henry.

Betty has weight gain and wears a pink robe

Betty’s sense of self and worth takes a devastating hit when she begins to gain weight unexpectedly. This change in appearance and looks breaks Betty, as she had revealed that she struggled with weight as a child when her mother began to make clear to her that her worth as a woman lies in being thin and beautiful. When Henry’s mother makes rude comments to Betty about her weight, Betty’s confidence takes even more of a hit as it becomes apparent that people are noticing her weight gain. This exchange with Henry’s mother also illustrates that the two still have a strained relationship. When it is suggested to Betty that she should start taking diet pills, she goes to her doctor in hopes of getting such a prescription. After running tests, the doctor discovers a lump on Betty’s thyroid that gives all that know her a scare while it is determined whether or not she has cancer.

Fortunately, it is discovered that the tumor is benign, but there is still no answer to why Betty is gaining weight. She ends up joining weight watchers which provide for her a place to talk about her issues and a supportive community of people experiencing a similar struggle, both of which Betty needs. She becomes hyper-vigilant in controlling what she and the family eat, leaving Henry so hungry that she finds him grilling a steak at midnight one evening. It is during this midnight snack of his that he and Betty have one of the most meaningful talks we’ve ever seen them share when he confides in her that he’s chosen the wrong politician to work for during that election cycle. He admits to feeling that his work is at a dead end and he wants more out of his career. Betty consoles Henry, encouraging him that he will figure out what’s best and make the right decision. This tender exchange reminds Henry of what he initially saw in Betty and reassures him that she is committed to moving forward in her life with him, breaking free from that which held her back with Don.
Mad Men (Season 5)

The high-energy vigor of season four was indicative of the many characters changing mindsets, the frenetic pace at which they were seeking to release themselves from everything stifling who they wanted to be. They had grown weary of the gender roles and the societal expectations that defined them, and instead, went about stripping away those labels so they could identify themselves. The vitality of the fourth season of Mad Men was unique, and by the fifth season, the feeling had shifted to trepidation. We could see the characters that we’ve gotten to know sense that the world was changing, and wondering if they would still have a place. The younger generation is gaining more stake in the company making the older generation question what lies ahead for them. Outside of Madison Avenue, the whole world is shifting leaving each generation to question what will become of their place in the world when the dust settles. By the time season five ends, we see Don walking away from Megan, the life he just created as a means or reinventing himself, while she is working on a commercial. Don is wondering if the trajectories of their lives fit together and questions if the changes he made will persevere. A blonde approaches him at a bar, and the audience is left to wonder if the old Don Draper hasn’t reemerged. We then see a montage of the characters in their new lives, each having re-invented themselves or left a part of themselves behind to embrace more of who they really are. We have seen more clearly in the fourth and fifth seasons of Mad Men, characters that thought they knew what they wanted, only to realize once they had what they thought they wanted, that they were still unhappy. Chasing temporary solutions to the larger unaddressed problem of what they want in life vs. what they are told they want has left each that we’ve come to know monumentally unhappy. Realizing that they were attempting to fulfill a goal that wasn’t truly theirs was the first step in being able to move away from their old lives and begin again anew. With eyes firmly extracted from the past, the only place for those at Sterling Cooper Draper Pryce to look is toward the future.

Written by Ashley Rincon

When she is not writing about the human experience or her most recent world cinema favorite, Ashley enjoys fawning over François Truffaut, reading Immanuel Kant, or drinking coffee black as midnight on a moonless night.

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