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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.

this is where we start to head into the emotionally uprooting territory of this exercise.

While I don’t believe that you need to shine a light on absolutely everything in the dark subconscious of your mind in order to have a healthy relationship, it is good to uproot the major things that get swept under the rug.

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.

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).

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!

(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.

These two are terrible for each other, but in some ways also perfect.

Over the course of seven seasons, Don's burned through two marriages, several mistresses, and countless one-night stands.

Below is a (highly subjective) list of Don's paramours, ranked in order from most to least appropriate match.

Given that Faye works in the same industry as Don, it's a miracle they haven't run into each other again.

The proverbial One Who Got Away, Rachel is a single woman who runs her family's department store, Menken's.

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