You know why? Cause Blair always end up running to Chuck’s arms again. Season 2, completely happy and ok with Nate? “Well we’re not meant to be you are my high school love and high school is ending”. Runs to Chuck. Season 3, nice guy from Columbia that was really nice… SHE RUNS TO CHUCK. I mean B you are awesome but the reason why Chuck knows he’ll never lost you and that he never gave up on you was that. If you really want him to feel like he could lose, end up this season with Humphrey instead of going to Chuck at 38 min of season finale.