Why they don’t work: First of all, Dan was a horrible person who felt entitled to Blair because he was “nicer” than Chuck (was he though??). Blair clearly dated him because everything had fallen through with Louis and she was questioning who she was.
Worst Scene: When Blair immediately forgave Dan for leaking the video of her confessing her love for Chuck at her wedding and then showed up at his house to tell him he had her heart, finally referring to him by his first name.
Special note from Kelly: Let the record show that I do not agree with them being on this list, but my co-writer felt very strongly about including them. *Sobs*