Don’s first-season moments with Midge are as rosy as rosy can be—they listen to Miles Davis, smoke a little pot here and there, and go their respective ways—him back to Ossining, her back to Bob Dylan-types and ‘I love you, Grandma!’ greeting cards.

In Don’s mind, the women he medicates with never change. In reality, they stay in the Village too long and wind up slaves to the needle.

Yes, in a quickly decaying New York, it makes sense that counterculture rears its ugly head in the form of heroin-addicted Midge and her would-be pimp husband.

A year or so away from the Velvet Underground’s ode to the drug, Village heroin use was in full swing. A 1965 Life Magazine shoot takes us inside the claustrophobic world of two addicts—a young couple who steal and hustle to feed their collective habit and leave their squalid quarters only to score (don’t even get me started on how much like the recent activities of Sterling Cooper Draper Pryce this is). 

Don tells Midge that he’s expected to see her in the Village, and of course he has! Don Draper knows nothing of what it meant to be an early bohemian woman—remember, Midge is living the boho life in 1960, a solid six years before little Peggy Olsen dares to venture over to a loft party. By 1966, Midge’s art career has gone nowhere, and the Dons of New York have moved on to younger and brighter things, and Midge’s flouting of convention has left her (literally) high and dry.

Destruction is on its way—to our SCDP heroes, to the women they throw money at, to the very city in which they all ply their trade. In a few short years, the Village will be uninhabitable for besuited businessmen like Don. The walls are closing in, and Don Draper’s only starting to notice.

*Footnote by- Angela Serratore