How would you describe Dan Humphrey in one sentence?

A middle class writer from Brooklyn who goes (or went? does anyone even still go to class?) to NYU. That seems to sum it up. We can all agree that is a pretty basic description of who he is, right?

Okay, well, most of the talk surrounding his character lately has had to do with his relationship with certain Upper Eastside Princess. Let’s take a few minutes to examine that relationship. Sure there are many things Blair Waldorf likes about him, like his taste in movies and books, his intellect, and his reliability. He has been a good friend to her over the past year or so, and they have discovered that they really do have a lot in common.

But let’s not forget the things Blair does NOT like about him, which she has articulated as recently as the very last episode. Things like his clothes, his residence, and even his writing.

So, to put it simply, the basic things that define him are the things she doesn’t like.

This doesn’t mean that they can’t be together. Of course they can. If there is anything Blair has proved over the last 4.5 seasons, it is that she has quite the ability for bringing about changes in men. She made lazy, apathetic Nate act like the perfect boyfriend (twice!), she caused Chuck to give up his bad-boy ways, and she even convinced Louis to stand up to his family and move to New York. So if she fell in love with Dan, I’m sure it wouldn’t take her very long to have him undergo a make over (preferably one that included chopping off that mop on his head), move to the Upper Eastside, and do something productive with his life (like start a business, or work with a charity).

Some might say: ‘But true love accepts you for who you are!’ and I agree, that is usually true. But what is important and fundamental to both of these characters is so vastly different that they would inevitably have to compromise if they were going to be in any sort of long term relationship. And let’s be real, Blair is never going to move to Brooklyn and start wearing Lands End. The transformation might be slow, and it might take a while for it to happen, but eventually Dan would simply become Househusband Rufus 2.0.

I know you might think about when he was with Serena, and how he didn’t completely change then, but Blair Waldorf is a whole different animal than Serena Van Der Woodsen. Serena was open to the whole Brooklyn, middle-class culture. She was perfectly fine with wearing jeans and flats and going to a little cafe for lunch or to some indie punk concert (or a Lincoln Hawk concert). But Blair Waldorf? She would never. Or, she would once, but she would hate it the whole time and never do it again. Dan may resist the changes Blair would push for, but Blair is too stubborn. She would never back down. And in the end, Dan would give in; or their relationship just wouldn’t work out.

I don’t know about you, but I don’t want that for Dan. What makes his character so great is that, even after all these years of interacting with the Upper Eastsiders, he still has an outside prospective. Putting him with Blair long term would ruin that, and then who would we have to serve as the voice of the masses? Vanessa? I shudder merely at the thought.

Note: This article assumes that the writers of Gossip Girl act with logical character development in mind and are able to recall the historical characteristics that they have defined for their characters, which are things I have doubted they have the ability to do on multiple occasions