Time for a more general one. It's not that he's guiltier than any other guys in Mad Men, far from it; every male character on the show seems to take their marriage vows with a pinch of salt. With Don though, the scale and quantity of his affairs is really something. From secretaries (Megan Calvert) to business associates (Rachel Menken), a wedding ring is just a minor hurdle to Don. One he jumps time and again. It's even worse when you consider he never learns. He split with Betty because she had run out of sympathy by the time she discovered his previous identity - turns out brazenly and repeatedly cheating on someone will do that to a person - not necessarily because of the identity theft itself. By the time he marries his secretary Megan, little has changed. He enters a string of affairs and the result is the same - divorce. At least Megan gets an acting career and a million dollars out of it though. Just saying.