Don Draper and Hank Moody both cheated and had drinking problems. Yes they were masculine in their energy and went for what they wanted; however that came with its own price(s), and they had too many vices/personal issues.
Also, Don Draper was a facade. A makebelief character he created, much like his own contrivances within the firm.
If one created an alter ego within their own dating life; I bet you could do many things you may deem currently difficult, as it’s a disassociation of self in a way; a mask so to speak. Alter egos can be a powerful tool. (There’s examples of a few athletes using sunglasses, headbands, bandanas, or arm bands, etc, which creates an alter ego).
I once pretended to be Australian for three weeks for fun when I was 22. It was a very interesting experiment. Because it brought out a different part of my personality and if I was rejected in any form, it wasn’t me as flowtheory being rejected, but the Australian being rejected. So in a way, I - my true self - was protected and in turn my identified self was left intact and unharmed. I still learned from that rejection, just without the hurricane winds which could sweep away some form of my internal well-being.