I have never liked her, she seemed much too crude to me. But I have recently seen her infamous Letterman show on youtube and a clip from Evita and that's what made me come here with the intent of posting the same question that started this thread. I definitely think she does. I'm a show biz person and I have Asperger's. The thing is that I can't connect to people one on one. But from stage I can. Off stage, everybody turns away after a short conversation and if I'm lucky they say "you're funny" because they don't know anything else to label me with. On stage, I'm prepared. I have rehearsed somebody else's words and am prepared as to how to deliver. I'm loved. I can break the barrier and appeal directly to their emotions.
I agree Madonna is a tough cookie. But that doesn't mean she doesn't face a lot of challenges. She's an endless fighter. And if she insisted on an interviewer not breaking eye-contact, that might easily her trying to face THAT challenge. In the video of "I'd be surprisingly good for you" she is not capable of much eye-contact. It's also typical for her to blink a whole lot.
The Letterman interview was her trying to outplay the IMAGE Letterman had made fun of in recent shows. She was trying to get back at him for portraying her that way. She said "if you want to play dirty, that's a game I'll easily beat you at" or something like that. Nobody got it, including Dave, although she had informed his team that that's what she would be doing.
She's got a whole lot of nerdy mind loops going on there, I can totally identify with that. (Unfortunately, I'm not a fighter.)
I just have to mention that Aspie women can be a whole lot more complex than Aspie men. Or maybe it's just comorbidities. I also am borderline, bipolar and very anxious. She probably has a low self-esteem thing going on because she's always majorly out to prove herself.
Oy, that was long.