'Mad Men' countdown: Who's the best woman for Don Draper?

A look at Don Draper's romantic relationships.

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'Mad Men' countdown: Who's the best woman for Don Draper?


Among Don Draper's many gifts is his preternatural ability to pick up women. As "Saturday Night Live" once spoofed so memorably, Don has a way of making women crazy by doing little more than staring off into the distance and being incredibly vague about his past. Over the course of seven seasons, Don's burned through two marriages, several mistresses, and countless one-night stands.

Whether Don is actually capable of being in a committed relationship is one thing, but it's also unclear just what kind of woman is really the right match for him. A free spirit like Midge? A professional equal like Faye? Below is a (highly subjective) list of Don's paramours, ranked in order from most to least appropriate match. We've limited this list to women 1) who are not paid to have sex with Don and 2) have ongoing relationships with him (sorry, Allison, the secretary Don sleeps with at the office Christmas party, and Joy, that chick in Palm Springs). Otherwise we might be here a long, long time.

Doug Hyun / AMC

1. Faye Miller Faye was Don's first serious relationship after his breakup with Betty and, aside from the blond hair, was pretty much her polar opposite. An ambitious woman who works for a consumer-research firm brought in to advise Sterling Cooper, Faye is intellectually and professionally Don's equal, and their relationship begins on an even playing field; he even tells her about his secret identity. But it's also short-lived. In one of the cruelest breakup scenes ever seen on national television, Don returns from a few days in California and tells Faye — over the telephone! — that he is engaged to his secretary, Megan. (Ouch.) It's worth noting that Faye is also the only woman on this list (except for Bethany) he never cheated on anyone else with — even Betty was "the other woman" for a single night during his marriage to Megan, lest you'd forgotten. Make of this what you will. Given that Faye works in the same industry as Don, it's a miracle they haven't run into each other again. But hey — there are still seven episodes to go.

Carin Baer / AMC

2. Rachel Menken The proverbial One Who Got Away, Rachel is a single woman who runs her family's department store, Menken's. Like Don, she lost her mother in childbirth; unlike Don, she's Jewish. Impossibly glamorous (check out that hat!), she's also smart enough to turn down his offer to run away together. "You don't want to run away with me; you just want to run away," she said. True, but Rachel does seem to hold a special place in Don's cold, icy heart. Out one night with Bobbie Barrett, he runs into Rachel and her new husband, and is clearly shaken.

Michael Yarish / AMC

3. Betty Draper Francis Don's long-suffering ex-wife, she also became his mistress for a single humid night at Bobby's summer camp. Older and wiser than she was during their marriage, Betty, unlike Megan, knows the emotional truth about Don. “That poor girl. She doesn’t know that loving you is the worst way to get to you,” she tells him. These two are terrible for each other, but in some ways also perfect.

Carin Baer / AMC

4. Megan Calvet Draper It's all Miss Blankenship's fault. If she hadn't croaked at the office, Megan might never have become Don's secretary, kicking off a chain of events that ended with Faye getting dumped and Don getting a new, younger, free-spirited wife. Given the circumstances that brought them together, Don and Megan lasted a surprisingly long time, but eventually his secrets proved too much even for her.

Jaimie Trueblood / AMC

5. Midge Daniels The very first mistress we meet on "Mad Men," Midge is an illustrator who lives in the Village and offers Don an escape from his conventional life in the suburbs. He ends the relationship when he figures out that Midge is in love with one of her beatnik buddies, but runs into her years later when she's hooked on heroin and struggling to make ends meet. Midge was fun while she lasted — she had some great wigs and a fabulous bohemian wardrobe — but she and Don were never going to be a permanent thing.

Carin Baer / AMC

6. Bobbie Barrett Don gets involved with Bobbie when her husband, a brash insult comic named Jimmy, stars in an Utz potato chip commercial for Sterling Cooper. She's older than Don's other mistresses but is otherwise the kind of strong-willed, sexually confident woman he tends to be attracted to. Still, Don seems reluctant about their affair, which is also an unusually messy one: both their spouses — not to mention poor old Peggy — find out about it. Don abruptly ends the relationship, leaving Bobbie tied to a bed when he discovers she's been gossiping about him with other women. Lesson learned.

Jordin Althaus

7. Suzanne Farrell Sure, she seems nice enough, but Suzanne — or as Sally calls her, "Miss Farrell" — ranks low on this list because, come on, it's so not cool to have an affair with your student's dad! Idealistic and starry-eyed, Suzanne was about to run off on with Don but ended up waiting all night outside the Drapers' house while Betty confronted him about his box of secrets. Talk about awkward timing!


8. Bethany Van Nuys Bethany is the prissy Betty look-alike Don dates immediately after the demise of his first marriage, but she's probably the very worst possible candidate for a rebound relationship. She's the type of girl who complains about going on a date to Benihana because it makes her hair smell icky and pressures Don to take their courtship to the next level so she can show him off at the country club. It's little wonder the relationship never goes any further than a few chaste kisses in a taxi.


9. Sylvia Rosen Nothing against the delightful Linda Cardellini (Lindsay Weir forever!) but Sylvia is kind of the worst. Actually, that's not fair; she's with Don when he's at his worst and is therefore guilty by association. She's also friends with Megan and lives in the Drapers' building, making their affair and its fallout especially messy. Did I mention the time Sally walked in on Don and Sylvia in bed together? Case closed.

Show Tracker is taking a daily look at all things "Mad Men" as the groundbreaking show begins airing its final seven episodes April 5.

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