Hi SwankyK! I would hope he would be a gigolo (sp?). I'd be saving my pennies for that experience.
I didn't notice if the grass he smoked with Midge and her friends really did anything for him. I'll have to watch that episode again. I do remember his taking a picture of Midge and one of her beat friends, getting sad because he figured she loved the guy, and then leaving Midge his bonus money to buy a car.
He did get a little paranoid when one of the beats mentioned the police being in the neighborhood.

If he were to go to the Haight/Ashbury district I think he would be driving the buses with tourists to stare at the hippies! I just can't picture him as being a free spirit...but, who knows?
Hopefully the MM series will last that long so we can find out!

Interesting... he would make a hot man call guy that's for sure, but I'm not sure we would ever see him in the seduction for money category.
Maybe he would take off to a remote tropical place where he really could carve out a new life. He would look good hanging by the beach in a pair of those tight 60's swim trunks like James Bond wore in Dr. No.
And since he is a real man of mystery, maybe he could disappear as a cool spy. Hummmm.... but I still think there was something that drew him into the the counter culture of Midge and her friends that he was intrigued by.It was such an explosive time being post two wars and just before Vietnam. Let's not forget Kennedy's assasination is around the corner too. I think the show will still be airing then and it will be a pivitol mood change to the era, thus the show.
I still think he did like the Mary Jane. Watch it again. Was this the episode that ended with a Bob Dillon song? He too was a big part of the counter culture of the era and gaining popularity in the Village at the time. Again, it's as if he doesn't really get it, but he's interested in the free spirit lifestyle.
I also can't believe that the words that the hobo told him when he flashed back to his childhood about being free didn't impact him. It's funny that right now he is living the same life that the hobo said he was so happy to be away from, because he was free from all the stresses of monetary obligations. Maybe I have read too much into this...

Swanky K and 60'schild, For some reason your posts made me think of "Hair" and Treat Williams going from hippie to square and then being sent off to Vietnam to die in the place of the guy he was pretending to be! Kind of Don Draper in reverse!???

Swanky K and 60'schild, For some reason your posts made me think of "Hair" and Treat Williams going from hippie to square (and then being sent off to Vietnam to die in the place of the guy he was pretending to be!) Shades of Don Draper/Dick Whitman!!!???

Sorry about the double (sort of) posts!!!

I think he would become a paper salesman for Dunder-Mifflin/Scranton and end up taking Pam away from Jim.

scfan, "Hair", I haven't seen that movie in a while, what a flashback! I never saw the play.
Anyone know how true to the movie it was? I remember the big deal about the nudity in the play.

What about Don going back and becoming a farmer? Or maybe he will sling a pack on his back and take to the open road - become a Hobo?

In the earlier episodes of Season 1 when Don was offered a better paying job at another agency and Don refuses, Roger asks him what he plans to do in the future and Don answered "not this". He had a longing look in his eyes like he would like to retire in some beautiful Island somewhere with a real family surrounding him away from all the rat race.

Don would run off to Paris and become a painter

or

He'd open a bar on a tropical island

or

He'd run off to Los Angeles to work in the movie business

I htink Don is a poet somewhere inside him - or some kind of visionary person - maybe a filmmmaker. He could go CIA!