Don’s depressed, under-stimulated housewife Betty sees a therapist whose office delivers another ode to the quadrangle; from the molding on the wall to the style of the carpet, the therapist’s office—the very place Betty should feel most free—is hauntingly claustrophobic. The wallpaper in the Draper kitchen? A boxy plaid. The miserable, vengeful young account exec Pete, who can’t decide if he wants to destroy Don or be his son (and sort of decides both), wears childish pajamas that are, yep, checked. The uptight, earnest Peggy often wears plaid; the vixenish Joan only wears solids.

On first watch, pay attention to what’s being advertised. On second, pay attention to who’s doing the advertising. The show pairs pitchers and products in a way that illuminates those characters’ deepest wants and fears. The loneliest man sells closeness; the ignored mistress sells visibility. Don starts the season pitching the Israeli tourism board—a wandering man selling the end of exile. On the season finale, his crowning achievement is his pitch for the Kodak carousel, a slide projector he promotes as “a time machine,” filling it with slides of his picture-perfect family as he weaves a story about what home is, what togetherness means and the importance of love and acceptance. Don is a liar, a philanderer, a man whose recklessness with other people’s affections is pathological—his pitch is bullshit, but beautiful.

Poor, sad Peggy sleeps with vile Pete, who then treats her like trash. She comes up with the slogan “Mark your man” for a lipstick campaign, a slogan that gets her out of the secretarial pool and into copywriting, but Peggy’s the one woman in the office who hasn’t marked her man. And that man’s big get is a Clearasil campaign, a product to treat or hide blemishes. Pete’s the character whose shortcomings are most apparent, whose failures are indistinguishable from his identity; Pete may be all blemish. The young and ambitious Ken, Paul and Harry, three young upstarts at the company, try to come up with ways to sell Richard Nixon as a presidential candidate—against John Kennedy.

The 1960 presidential campaign, according to most pop histories, was about image, youthfulness and mythology, and in many ways Mad Men reflects the conflict between glamorous energy and square predictability. But in its shifting character pairings, the show goes a step further than asserting that young attempts to topple old; instead, it wonders just exactly what we mean by conventional. When Betty warily befriends new neighbor Helen, she’s horrified to discover Helen’s divorced, employed and voting for Kennedy. But Betty winds up giving Helen’s son a lock of her hair and developing a bizarre kinship with the nine-year-old. Who’s the rebel here, again? Joan, ostensibly the independent and sultry queen bee of the office, ends up being much more attached to rigid protocols than the squeaky-clean Peggy. Don tries to prove he’s got far more vitality than his boss Roger, but Roger’s heart attack leaves Don wrecked.

What do you want?, Mad Men asks its characters and audience. What you think will satisfy you won’t, and all you’ll be left with is the chance to watch Mad Men over and over. Which may be pretty satisfying after all.

Mad Men season one is available on DVD now. See “Pieces of Draper,” for more.