@Butterflygal said:

With the exception of Joy, Megan, Faye, the older rich woman in season one, and Sally's former teacher, most of his paramours died.

The older rich woman as in Rachel Menken? Yeah, she did die. But the older rich woman Bobbie Barrett didn't. I think that it's the deaths, rather, that are exceptional.

Didn't Midge die from an overdose.

We don't know that — although we do know she was a heroin junkie who was losing the fight. That is horrible stuff.

Even Betty had a grim future.

Yep. Back in those days, cancer was an even more confirmed death sentence than it still can be today. So, yeah, that pretty much doomed her to that sad demise.

I wonder how his last lover, the waitress fared?

She was troubled, but nothing to say she was going to die.

I recall Rachel dying, but thought she and Don were the same age.

@Butterflygal said:

I recall Rachel dying, but thought she and Don were the same age.

Okay, so your "older rich woman" was...who? Bobbie?

Yes it Bobbie I believe.