When do you think Dan will propose to Amy? That is of course if he does do it
On the one hand, Dan seems EXACTLY the kind of person who would enjoy a huge elaborate proposal that makes things all about him. On the other hand, Amy would hate it, and I imagine he’d know that.
It doesn’t seem beyond the realm of possibility to me that Dan would be open to at least an engagement as a way of managing the political problem – as @wecouldstillbegreat pointed out, that’s the solution he jumped to when Selina was pregnant.
And there would be some definite positives from his perspective. He’d get to have an ongoing relationship with Amy – which would almost certainly include sex (eventually) – without ever having to express himself. He’d get to maintain the pretence that he’s completely heartless when it comes to Amy, and he’d even get to act as though HE was doing HER a favour. There’d be no messy emotional vulnerability, no threat to the persona that Dan has put considerable effort into building.
On the other hand, I really can’t see Amy tolerating that scenario for any prolonged length of time. It would be difficult to navigate even if Dan was a sensitive, caring person, and he emphatically isn’t. I think she’d be almost bound to resent him for it.
It seems likely that she only stayed with Buddy because of the potential damage to her career if she left – but in a scenario where she believed that Dan was indifferent to her and their child, I’m not sure even a political scandal would be enough to make her stay.
I think Amy would build some kind of life-raft and get the hell away from him – unless he found some way to convince her that he actually DID care. And with the way Dan has behaved over the years, I don’t think any single gesture – even a proposal – would be enough.