“He’s devastated me, but he’s also made me happier than I’ve ever been.” - Blair
This has been the Chair argument for a while that although Dan makes her happy, he doesn’t make her as happy as she is with Chuck and that happiness makes up for the other “devastated moments”. Blair seemingly confirms this with her words and actions in the finale but where’s the proof writers? When you look at Blair’s happier scenes with Chuck and then compare them to her scenes with Dan, I think you’ll find that the expression on her face emulates the same level of happiness with both boys. There’s not much difference, really, the striking difference is that I found there are more happy scenes with Dan than Chuck but that might just be because of my Dair preference making it easier for me to remember the happy moments with Dan, so I’ll let that point go.
However then look at the moments where Blair has been hurt. Here I really can confidently say the choice of scenes where Chuck had hurt Blair was far greater than with Dan. In fact, those 3 moments with Dan are pretty much the only 3 times Blair has come close to being hurt by Dan and even then it’s only the Dowry moment which came close to really hurting her (and she was over it a scene or so later!). The other two moments left her feeling more betrayed or disappointed that Dan hadn’t lived up to the trust she had placed in him. Again, she got over those two moments quickly and what’s more, in all 3 cases Dan was quick to sincerely apologise.
Compare this to Chuck. There’s no comparison between who has hurt Blair more, it’s clearly evidenced that Chuck has “devasted” her to an incredibly low point. I’ll give him a bit of a free pass for some of his season 2 actions because I can actually accept that daddy issues argument as Bart had just died. However season 3 and 4? It’s all just pathetic excuses. He may have felt the pressure to maintain Bart’s legacy but this time round he has had a chance to grow up and he also had a really supportive family in Blair and Lily. So when he makes those decisions - from agreeing to the trade and manipulating Blair into it - they’re cold, calculated, selfish decisions that heartlessly use Blair for his personal gain. He doesn’t even realise how wrong it was, it takes almost 2 years to actually give her the apology she deserved. His first reaction is to blame her, how do I sympathise with that?
And his continual self-centered manpain and manipulation for the rest of the seasonThen’s there’s his outburst in season 4. You can say that it was a heat of the moment thing where his temper got the better of him but what about his reaction later - “so, you’ve finally come to your senses?” - WITH NO APOLOGY?!!!
Therefore, in conclusion
before I begin a massive Chair rant, the main difference between the two boys is the “he’s devastated me” part. Based on what we’ve actually seen on the show, both boys are capable of making her happy to the same extent but only one can do it without the expense of total devastation. Her choice should have been Dan.