Blair and Chuck are a great couple. And many knew that from the moment that the two kissed. but for some reason the writers got rid of the couple and went back to Blair and Nate, and now Blair is single.
This may not make sense, but i think that one of the reasons for this, is Chuck. No it's not because he's too mean of too much of a jerk. He was too nice and soft.
Chuck was there for Blair when they were together as he was falling for her. And that softened the hard cover of the jerky, upper class, snobby, player. And that may have scared him and he was losing his image. *being a jerk and a player*
Chuck may seem like the kind of guy that no matter what he is always a jerk. But on the inside, I think we have all seen that really he is soft and caring. But that coming out scares him, so we don't see it a lot.
I think that for everyone to see this side of him, the toon needs to bring out that really chuck is a nice guy. And the only way so far is doing that through Blair.