Mad Men Season 4

This.

 

Like horse dentures. Which made the whole hookup even skeevier.

 

Don was eyeing her seriously about . . . say . . . seven seconds after he could
first see he was off the hook re the security clearance. It was about as
subtle as a Southern Cal booster -- and hilarious.

 

She was in Hot Tub Time Machine. She was the girl Daryl from The Office "cheated" with.

 

As far as women Draper has boinked, I think she's about in the middle. She's no Betty, but she's still a B-plus.

 

She was also in a movie called "Lost and Delirious" where she and Piper Perabo were lesbian lovers at an all-girls high school. I shit you not.

 

She's elegant and doesn't fit the usual American stereotype of what a beautiful woman should be. She's not blond, she's tall, she's slim without being anorexic and she has this grace about her.

And she's from Montreal, the city with maybe the classiest women outside Paris or New York

 

I've been to Montreal a couple times, and I can certainly vouch for JR's assertion.
As can Win Butler.

 

Irreconcilable differences = I'm a bigger star that the loser I'm with. Now I can do whatever the hell I want now that I'm big time!

 

Don is back to wearing the hat. That's all I got.

 

Not to mention his reluctance to adopt her Scientologist ideology.

http://www.usmagazine.com/celebritynews/news/elisabeth-moss-files-for-divorce-from-fred-armisen-after-11-months-2010209

 

Which goes a long way towards explaining how she's always seemed more
than a little Out There.