Don's conversation with a stranger named "Connie" at Roger's party was telling.  It presented the first instance where Don actually opened up truthfully to anyone about his past.  The viewer sensed a palpable sense of relief and ease in his demeanor.  It was as though he was at Confession with a cocktail and a smoke.  How interesting it is then that Conrad Hilton, someone we only knew as Connie has now tracked him down at Sterling Cooper.  Don now has a gateway to find a meaningful connection with a mentor who relates with his humble roots, and thus can deliver him to the promised land of super-stardom.  Of course if Don actually nibbles, it will present an interesting dilemma in his home life.  The truth will come out and Betty, and her new spiritual ally baby Gene will be a force that threatens to tear everything down.

tgcat,
I'm not sure what you mean. Don keeps his work life/home life/private life notoriously seperate. I don't see how Hilton being privy to a little humble beginning info could damage his home life with Betty. She knows next to nothing about him anyway. No one is born a fully-formed executive.

I guess what I am trying to say is that never before has Don considered his alter ego empowering, but then he meets Conrad Hilton who instead of burying his past, features it.  In a sense, the truth sets him free.  Don might sense the truth might do the same for him.  What fascinates me most about Don Draper is the fact that he is the ultimate Jay Gatz/Gatsby figure - a man who has tried desperately to escape from his past only to have the ghosts of that past continually haunt him.  Connie seems like a kindered spirit - one who will empower Don to eventually fess up, slay the dragon and move forward.

Cooper, of Hilton: "I met him once. He's a bit of an eccentric, isn't he?"

Hehe...