I never liked Don Draper, mainly because of his philandering ways while married but in this episode, I saw him in a surprisingly generous light. Albeit, he was no longer married but his attitude seemed different, as the opening scene with the casting model in the chinchilla coat attests, his usual mode of seduction was not being used in a selfish way, possessing both the faithful, idealized, naive wife and partner-in-crime/soulmate mistress but strangely in elevating the women, away from their worldly reality. For example, he guides the casting model to successfully perform her fantasy role as she stands clueless in the beginning.
When the airline stewardess spills her glass of wine on the rug and she bends down to clean it up, Don saves the fantasy but fluttering the blanket down to cover the stain, reminding her of her present role.
In another instance, Don sees something in a diner waitress. He wants to find out where the association comes from and wants to make a connection, not a sexual one but a deeper one. And in the beginning, we think the waitress, as she carries around a copy of John Dos Passos and reads in her off-time, would be capable and receptive of such an exchange but she sadly disappoints. What passes is the crudest form of connection, the waitress misinterprets a large tip given by Roger for making fun of her as a proposition for paid sex. Don does the gentlemanly thing and has sex with her but what he really wanted was to find out why she was capturing his imagination. She kills the fantasy with her low self-esteem.
In both cases, the service women were idealized in Don’s imagination but they sold themselves short.