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We learn from this exchange that Dan has been waiting a whole week for Blair's text or phone call but she has mysteriously been ignoring him all week. Knowing that the obstacle to their relationship is the fact that Blair wants to become a powerful woman before asks Epperley to hire Blair as her assistant in the Modern Royalty photo-shoot.

Epperley calls Blair who in the meantime has told Dorota that she's had an epiphany about her romantic future but doesn't want to deal with it.

In the Fifth Season, Dan still possessed feelings for Blair.

Blair, however, had seemed to have forgotten any romantic feelings towards Dan due to her upcoming marriage to Prince Louis Grimaldi of Monaco.

Dan learns, via Chuck, that Blair said the kiss she had was life-changing, and clearly impressed by this piece of information, starts rambling about how much Blair is better when she's not around Chuck.("She's intelligent, She's intuitive, She weeps when she watches Nights of Cabiria") and finally tells Chuck that if Blair's happy, he should let her be.

Chuck has now understood that is Dan the one who Blair has kissed, and we see him exiting the loft and calling Epperley to ask her "One More Favour".

Thus begun the start of their friend/enemy relationship.

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Later as the season progressed, Dan was the one who comforted Blair after being humiliated by her own mother and Serena.While Dan is getting ready he phones Eric for some advise but all Eric can say is "You Really Like Her." He also naively believes that Blair concocted this event to elevate Dan's social statue.When he comes to the fashion book thinking Blair called him here both of them find out it was Chuck's idea and all Blair says to Chuck is "Dan May Not Be Royalty But at Least He's Not a Child".They are depicted as the two intellectual-equals in the show.Blair also admits that she fears him as a rival in Damien Darko, when they both are interns at W.

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