It's heartbreaking just to look at this photo, isn't it? Longtime Mad Men viewers understand why.
This is a shot of Joan from the episode "The Other Woman." It's the 11th episode of season five.
Don must make a difficult pitch on Mad Men. "The Other Woman" is the 11th episode of the show's fifth season.

Mad Men Season 5 Episode 11 Quotes

Pete: What would it take to make you a Queen?
Joan: I don't think you could afford it.

It turns out he wanted something we weren't prepared to give. Something very unorthodox.

Pete [to Joan]