There is a wide line, but I'm just saying I understand where the character is coming from. I'm the type that laughs at my pain and lives in my truth. I need someone that's the same way. With the way she opened up about the foul shyt she's done he probably assumed it was fair game to make jokes about it. And if not a mature woman would tell him straight up "that's too far" and keep the conversation moving. It seems you're putting the whole burden of maturity on the man while excusing Molly's behaviors.
I do get what you're saying about the appropriate type jokes to tell to people you're just getting to know. I'm the type that takes it to the next level quick so I know who I'm dealing with and don't waste my time if they can't handle a personality like mine.
Of course Molly is insecure and immature, and all those things! That is the show. And, sure, maybe her departure was over the top, but she doesn't owe that guy much of anything, two dates, and he's acting like that? No personal disrespect, but your approach is pretty ridiculous. I'll just offend people until I meet someone who isn't offended? not very empathetic or understanding or the wide range of personalities or people. If someone is too immature, to deal with, you never meet them at their level, you stay on your own.
And, I am someone who isn't easily offended at all, can take and make jokes at my own expense always. But, not everyone is like that, in fact, most people aren't, and in fact many who claim they aren't, they really are, in my experience. Like I have a fairly troubled background, from drugs, alcoholism, and jail, working low level jobs when I was younger...no issue talking about it, or laughing about it, or someone laughing at me. But, if on a first date I made like a joke about her getting a parking ticket and she said....
"Well, at least I never sat in jail on my Mom's birthday, and had to call to tell her, after getting strip searched in county"
I could laugh that off, and just note that about her, but that would be way past appropriate.