To celebrate the premiere of Mad Men's final season, let's look back at the bevy of intellectual brunettes who have loved, lost and even sometimes married the cipher at the heart of the AMC drama.
The first woman Mad Men viewers ever see with Don Draper, free-spirited Midge symbolized the cultural divide that was to take over the '60s, in the too-pat way that occasionally marred the show's first season. Her bizarre reappearance as a heroin junkie in season 4 served as an example of the way the dream of the '60s failed many of its believers, as well as a reminder of Mad Men creator Matthew Weiner's continual annoyance with the hippie movement.
Many women have called Don Draper on his BS over the years, but none more viciously than Rachel Mencken, a Jewish department-store magnate who captured Don's attention at the end of season 1. When Don, nervous that his secret life would be revealed, invited her to flee to California, Rachel saw the real man underneath the chiseled jaw and expensive suit: "You don't want to run away with me, you just want to run away. You're a coward." The power of the Draper image had never seemed more of a lie.
As his marriage crumbled, Don's affairs grew riskier, culminating in his brief fling with Ms. Farrell, his daughter's teacher, and one of the few flower children Matthew Weiner seemed to respect. A bright, idealistic dreamer, she didn't deserve her eventual fate – waiting forever in Don's car while he got ready for an escape that never came.
At first, it seemed Megan would be Allison all over again, an admiring young secretary who succumbed to Don and paid the price. But savvy viewers of Mad Men's fourth season knew there was more to Megan than first appeared; whether it was romantic serendipity or the culmination of a months-long plan, her love eventually made Don happier than we'd ever seen him before. Their bliss was soon shattered by the usual catalog of Draper sins – alcohol, selfishness and infidelity – but there are a number of fans (most notably Tom and Lorenzo) who think they've got what it takes to stick out the rough patches.
Don Draper's always had a virgin-whore issue, but Mad Men's sixth season made it explicit. Don's affair with his deeply Catholic neighbor started ugly – not only was Don back to his philandering ways of season 1, but he was doing it with the wife of his only real friend – and got worse from there, as Don's controlling tendencies verged towards outright emotional abuse. Though both had multiple opportunities to get out, Don and Sylvia kept escalating the affair until it exploded in a shocking moment of emotional violence in "Favors" – fitting for an episode all about Vietnam.
Despite (or because of) Don's many affairs, there's one bond in his life that's outlasted the all others: his rocky relationship with secretary-turned-protégé Peggy Olsen. It's never been romantic – and, we pray to Weiner, it never will be – but underneath the screaming matches and the battling egos is a deep love. Of all the things we hope for in Mad Men's final season, the repair of Don and Peggy's connection is at the top of the list.