I definitely think its time has a little time to suffer he has always had it easy with Blair, she takes him back pretty fast, I know Its love but hey she deserves a great guy and what more than Dan, Serena is a douche for a girl what is she the second coming? Seriously come on Dan is always waiting around for her to make up her mind or do something thats why he misses out on stuff.
Both Blair and Dan deserve that relationship and make manhattan roar, hahahaha I really think its interesting why not?, I mean the prince sure he's a prince but he was kind of boring Blair needs fun someone that puts her in her place and Dan is that someone.

HIMYM