‘Mad Men’: Don Draper’s Top 5 conquests

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To celebrate the return of Mad Men (currently airing on Tuesday nights on Sky Atlantic) and Don’s recent new marriage to his secretary Megan (for however long that might last), let’s take a scandalous look back at some of the other women in Don Draper’s life…

> Buy the Complete Seasons 1-4 boxset on Amazon.


Ah Doris, the diner waitress. As Don wakes up from a particularly rough evening partying from winning a Clio award, the surprise isn’t that he’s woken up next to a strange woman (this is Don Draper after all), but that it wasn’t the same woman he went to bed with, and a whole two days have passed in-between.

We’ll never know how he managed to seduce Doris from her waiting duties, and neither, it appears, will Don. Still, he’s courteous enough to let her know that he’s had “a really great time”, before shooing her out the door, as dazed and hungover as he’ll ever be.

Bobbie Barrett

Probably one of Don’s few conquests (except, perhaps, Betty) who is as entirely messed up as himself, it’s clear from the start that Bobbie knows how to have a good time and is using Don just as much as he’s using her.

In this way the pair work well together, with Bobbie’s remark of “This is America. Pick a job and then become the person that does it” sounding not unlike something Mr Draper could be telling Peggy with some distain in the office.

However, their similar lusts for power becomes too much for even our predatory salesman, who leaves Bobbie at first amused and then distraught, tied half naked to the hotel bed posts.

Midge Daniels

One of the key moments of the pilot that sets the tone for the rest of the episodes to come is the realisation that Midge is in fact nothing but a side affair for Don, as he slips into bed at night amongst his children in his house with Betty.

In this sense, throughout the first season Midge remains a calming factor for Don alongside his artificial marriage with Betty, and he even asks her for copy writing advice to find out exactly what it is that women want.

However, by Season 4 this delightful beatnik has lost all of her artistic creativity, becoming badly addicted to heroin, with Don paying her for a painting, then quickly leaving.

Faye Miller

A tough, modern woman who has the admiration of Peggy and many other people in the SDCP office besides, why this never worked with Don still remains a mystery.

As one of the few women that Don admits his true identity to (his drunken confession to Doris doesn’t really count), perhaps the real issue is that Mr Draper enjoys the excitement of a younger, less confident model, something that as a hard working freelance consultant, Faye just can’t offer him.

Rachel Menken

Not only is Rachel the girl that inspires Don to utter the immortal lines “What you call love was invented by guys like me to sell nylons”, she also inspires the first of Don’s spontaneous decisions – here to escape with him to LA – seen later on in the series when he suddenly proposes to Megan.

Rachel’s rejection of his offer hurts the relationship and whilst it seems that in Season 2 Don is only momentarily shaken by realising she is now married, he later gives the name of Rachel’s husband as a pseudonym to enter an underground club with Roger, showing what could have been is still preying on his mind.

Which of Don Draper’s conquests is your favourite? Let us know below…

> Buy the Complete Seasons 1-4 boxset on Amazon.

Watch the Season 5 trailer…