Dan in the latest chapter of what might have been is almost sweet- it really warms my cold dead heart everytime he does something even remotely nice for Amy
You know, half the reason Dan being nice to Amy happens so rarely on the show is precisely because it has such an impact on the audience. When you have a writing tool that powerful in your kit, you use it sparingly, to preserve its power.
I could bemoan my writing failure in making Dan NICE, but rather than do that, I’ll take a step back and explain where it comes from.
Because, for all that he’s a toxic waste dump of a person, when Dan is with Amy, and especially when a romantic connection is on the cards, sweet is really the best word to describe him. Compare the sleazy way he hits on Brie with his line to Amy in 5.02, “it’s just little ole you, in that big ole room.” It’s the same in 4.04 and, though we didn’t see, I’d be willing to be on 6.09 too. He doesn’t ogle her and he doesn’t insult her or neg her. Sometimes the old ways are best, and on some level I think Dan knows that, because his approach with Amy is very simple in some ways – he makes her laugh, and he plays up a sense of intimacy between them.
As vitriolic as Dan and Amy can be with, oh, everyone else they know, if you examine the dialogue that’s just between them (especially from 3.08-5.02), it’s actually remarkably pleasant-spirited by Veep standards. That’s why it’s so jarring in 5.03 when Dan aims his usual brand of nastiness directly AT Amy. He really hadn’t done that before – in fact Amy seems to turn him into a loveable asshole, instead of the asshole-asshole he is to everyone else on the planet. He becomes a lot less sufferable as a character in season 6, and part of that is being removed from her influence.
The other thing I was thinking about was sex, because I have to suspect that if Dan has had even half as many partners as the show implies, he’s got to be pretty damn unshockable at this point. Which means that he has the common sense to realise that Amy will be more interested in sex with him if she enjoys herself, and that part of that is not making her feel embarrassed or awkward for expressing her own needs. (The show implicitly compared Dan and Buddy’s approach to sex in I can’t remember which episode – 6.03, maybe? – where Dan makes a comment about the woman he’s meeting “likes to talk first” specifically paying attention to HER needs, though it’s doubtful he cares about her beyond that. Whereas Buddy didn’t seem to pay attention to what AMY liked, and seemed to consider her lack of enjoyment of sex as a spiteful act, rather than a sign that she needed something different. Amy’s spent too much time around the Jonahs of this world to get an erotic charge from dirty talk, I think.)