Philandering New York adman Don Draper (Jon Hamm) has spent the first three seasons of Mad Men swinging between his model wife, Betty (January Jones), and a series of tawdry liaisons.Philandering New York adman Don Draper (Jon Hamm) has spent the first three seasons of Mad Men swinging between his model wife, Betty (January Jones), and a series of tawdry liaisons. (Frank Ockenfels/AMC)

WARNING: THIS PIECE CONTAINS SPOILERS ABOUT MAD MEN SEASONS 1-3.

The 1960s period drama Mad Men would be nothing without its mysterious anti-hero, the slick adman Don Draper (Jon Hamm). As one of his colleagues at Sterling Cooper once cracked, “Who knows anything about that guy? Nobody’s ever lifted that rock. He could be Batman for all we know.”

Two Draper traits are indisputable: his gift for delivering brilliant ad pitches and his powers of seduction. The philandering character has bedded an impressive array of ladies during the show’s run, and his taste in women reflects the contradictions of his precarious double life.

There’s a consistent madonna-whore cast to his love life, with Don vacillating between his sheltered, Grace Kelly-esque model wife, Betty, and the more liberated, career-minded women who satisfy him in bed. Whether the dashing creative director will be able to give up his Casanova ways and find the connection he craves remains to be seen. (It seems unlikely, given Don’s belief that “love was invented by guys like me to sell nylons.”)

With the fourth season of Mad Men premiering on July 25, we present a guide to the women, past and present, who have helped shed light on one of television’s most enigmatic, compelling characters.

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Betty Draper (January Jones)

First appearance: Season 1

Nature of relationship: Married in 1953, Don and Betty achieved picture-perfect middle-class domesticity – without any of the bliss.

Heat factor: Judging from their passionate arguments, this genetically perfect couple was once a scorching item, but unspoken resentments have led Don into the arms of strangers, and Betty into two pseudo-affairs (three, if you count her afternoon with her washing machine).

Where things stand: After finally cluing in to her husband’s double life in Season 3, Betty announces: “I’m going to Reno, and you’re going to consent.” She was last seen boarding a plane with her new love, Henry Francis.

Odds of it continuing: Very high, if only for the sake of their kids.

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Midge Daniels (Rosemarie DeWitt)

First appearance: Season 1

Nature of relationship: A mutually supportive, no-strings-attached affair. Autonomous, free-spirited illustrator Midge understands Don’s creative side, and the pressures he faces at work.

Heat factor: Volcanic, particularly since the independent mistress is the polar opposite of Don’s needy wife. Midge’s motto: “I don’t make plans and I don’t make breakfast.”

Where things stand: She declined Don’s invitation to run away to Paris. It’s a testament to Don’s charisma that his parting gift to Midge – a cheque stuffed down her bra – managed to come off as a genuinely loving gesture.

Odds of it continuing: Highly unlikely, given that Midge was already making eyes at a beatnik poet before Don was out the door.

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Rachel Menken (Maggie Siff)

First appearance: Season 1

Nature of relationship: The head of an upscale New York department store and a high-profile Sterling Cooper client, Rachel causes sparks when she rejects Don’s idea to promote her store with coupons. Initial friction gives way to a dalliance that makes adultery look almost romantic. An independent, solitary career woman and kindred spirit, Rachel is one of the few women Don confides in.

Heat factor: Smouldering. Don and Rachel share a few passionate nights together, but their bond is based more on a shared loneliness than lust.

Where things stand: She declined Don’s invitation to run away to Los Angeles, calling him a coward in a bittersweet conclusion she had forecast from the start.

Odds of it continuing: Some diehard fans feel Rachel is Don’s soulmate, but a reunion seems out of the question now that she’s married someone else.

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Bobbie Barrett (Melinda McGraw)

First appearance: Season 2

Nature of relationship: After comic Jimmy Barrett causes chaos while shooting a commercial for Utz potato chips, Don informs Jimmy’s wife and manager, Bobbie, that she needs to keep her famous hubby on a tighter leash. A business relationship turns tawdry, as both Bobbie and Don resort to using sex to assert dominance and gain the upper hand.

Heat factor: Thermometer-busting — in a dirty sort of way. These two created one of the most controversial scenes in Mad Men history.

Where things stand: Their relationship ends abruptly when both Jimmy and Betty get wise to the affair.

Odds of it continuing: Never? Bobbie is the only woman who made Don feel cheap.

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Joy (Laura Ramsay)

First Appearance: Season 2

Nature of relationship: Don and Joy meet in the bar at a California hotel where Don and Pete Campbell are staying during a business trip. It turns into a decadent, debauched vacation fling that only exacerbates Don’s existential crisis.

Heat factor: Tepid. Joy was another satisfied customer, but Don was too distracted by their class differences to truly enjoy himself.

Where things stand: He declined her invitation to run away to the Bahamas, possibly because her nomadic, upper-crust lifestyle was too weird for him.

Odds of it continuing: No chance.

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Anna Draper (Melinda Page Hamilton)

First appearance: Season 2

Nature of relationship: Don stole Anna’s husband’s identity, and in exchange for generous financial support, the widowed piano teacher has agreed to keep the fact a secret.

Heat factor: Their relationship is platonic, but there’s warmth to it. Anna has become a friend, confidante and maternal figure for Don.

Where things stand: She gave Don advice and a tarot-card reading, both of which inspired him to go home to (try to) save his crumbling marriage.

Odds of it continuing: High, as Anna is one of the only characters who knows the truth about Don’s past.

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Shelly the stewardess (Sunny Mabrey)

First appearance: Season 3

Nature of relationship: She took Don’s drink order on a business flight. A one-night stand ensued, but it was empty — Shelly clearly isn’t Don’s type.

Heat factor: Any excitement generated by Shelly’s cable-approved nudity fizzles once you see the bored, drunk look on Don’s face.

Where things stand: Their tryst was cut short by a hotel fire alarm.

Odds of it continuing: None – unless Shelly miraculously morphs into a brunette.

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Suzanne Farrell (Abigail Spencer)

First appearance: Season 3

Nature of relationship: Miss Farrell is Sally Draper’s schoolteacher. The first time we see her, she is leading her students in a celebratory dance around the maypole. Once Don asks Suzanne, “Are you dumb or pure?” it’s only a matter of time before this parent-teacher meeting turns erotic. The liaison is partly an attempt to recapture his lost innocence.

Heat factor: A fairly fiery affair, especially since both Don and Suzanne are always aware they could be caught.

Where things stand: On the heels of an intense argument with Betty, Don phones Suzanne to say he can’t see her anymore.

Odds of it continuing: Possible, given their amicable parting. Then again, fans of the show never warmed to her character.

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Peggy Olson (Elisabeth Moss)

First Appearance: Season 1

Nature of relationship: Peggy began as Don’s secretary and has gone on to become his copywriting protege. He is also instructing her in the art of erasing all traces of one’s past.

Heat factor: Zilch.

Where things stand: Peggy’s one ill-conceived romantic overture – an attempt to touch Don’s hand – was rebuffed with the following zinger: “I’m your boss, not your boyfriend.”

Odds of it continuing: Nothing romantic is bound to happen here. But Peggy’s loyalty to Don and her emulation of his style are guaranteed until the series ends.

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Joan Holloway (Christina Hendricks)

First Appearance: Season 1

Nature of relationship: A one-time secretary and longtime colleague of Don’s, the coolly efficient bombshell anticipates his professional needs and respects his privacy.

Heat factor: Off the charts, although they’ve never consummated their feelings (as far as we know). If Joan and Don ever mate, they’ll explode – or live happily ever after.

Where things stand: Joan’s marriage and resignation from Sterling Cooper caused a temporary separation, but she’ll be back in the workplace for Season 4.

Odds of it continuing: Here’s hoping. These two are an ideal romantic match, though neither of them knows it yet.

Season 4 of Mad Men begins on July 25.

Lee Ferguson writes about the arts for CBC News.