People often put down Dair for being a surprise. Dair never got a constant build up, but the quality scenes they received over the years were enough to give them the greatest buildup on GG. I believe the creators of the show when they say Dair was always suppose to happen. If you don’t believe me, just read and think about it without bias.

I think by now the show has absolutely established Chuck is Blair’s great love, the crazy love. But he is not her happy love. I feel like Chuck was often being to compared to Blair’s “right” love, her “real” love, her “happy” love, a person who didn’t even exist.

This goes back to 3x18. In that episode Blair knew she loved Chuck, she loved him so much that she didn’t think loving someone to that extent was even possible. But she also told him that is not what she wanted. She didn’t like the person she was in this love.

Blair: “I want what Dorota and Vanya have. Real love, pure and simple love”
Chuck: “You will be bored within 5 minutes.”
Blair: “Better bored than ashamed of myself”

It’s so funny how this mirrors how Dair and Chair fans feel. Chair fans call Dair boring, and Dair says I would rather be bored with my couple than support a couple I am ashamed of.

I felt so bad for Blair in 3x18. She had experienced this all consuming, great love, full of games, and short lived thrills but she wasn’t happy. It’s like that one great one night stand. It might have been the greatest sex, and greatest moment of your life but afterward it just sort makes you dislike yourself.

Dorota had a similar conversation with Blair too that day.

Blair: “When I saw you how happy you and Vanya are, I realized how unhappy I am.”
Dorota: “I wish you to be like me one day, to find right love, good love”

In Blair’s world real and simple love that makes people truly happy don’t exist. She never realized what happiness in love felt like because she has never seen anyone with the right, simple love. In this conversation Dorota doesn’t say I hope your relationship with Mr. Chuck turns good, and becomes simple one day. She is speaking of a person Blair still hadn’t found. A guy who would give Blair the real, pure and simple love. Dorota hopes that Blair “finds” that person one day.

In the same episode they put the simple Dan in Blair’s path. When she tells Dan she has become the person he always thought of her, he says “you are not that bad.” And this actually makes her feel better. he says Chuck and Blair are meant to be, and though she smiles she goes on to pity herself saying who else would love her after what she had become. Later on when he watches her watch Chuck he tells her that she deserves to be with someone who makes her happy. This was no longer Chuck, Dan was talking about. This was the same guy again, the one who would be Blair’s real love, and right love. The one who would make her happy.

Would it be too far-fetched to say they were setting up Dan as Blair’s “real, pure and simple love”? Because they are clearly speaking of a person other than Chuck here, someone who would give Blair everything she has been missing. And we all know a new guy in GG means nothing.

A season later Blair has a opposite conversation with Chuck in 4x22. By now she has come to understand what life without Chuck is like.

“What we have is a great love. It’s complicated, intense, all consuming, no matter what we do, and how much we fight, it will always pull us in. What’s mere happiness in the face of all that?”

She puts down happiness by calling it “mere happiness”. It’s like she already knew by being with him she won’t be happy. And who doesn’t want to be happy? Everything we do in life, we do it to be happy. In season 5 she is miserable and all she wants is happiness again. Blair has fought harder to be happy than anyone else in the show. She looks so sad and she mocks this thought at the same time when she says “what’s mere happiness in the face of all that?” She clearly knows that if she had it her way she would rather be happy. But she hasn’t found that love yet, the one with happiness.

Later on in the same episode, again speaking of happiness she says

“Chuck, that’s not the important thing, people don’t write sonnets about being compatible, or novels about shared life goals and stimulating conversations. The great loves are the crazy ones.”

She talks about her “simple love”. Again the guy that she still hasn’t found. She tells him people do not write novels about shared life goals and stimulating conversations. She is once again comparing Chuck to a person she still hasn’t found. The same person who was suppose to give her the real, pure, simple love. The one she was suppose to kiss someday for herself, someone who she would’ve shared stimulating conversations with. The someone who would write sonnets and novels about her. That person who never showed up to claim her, and she was disappointed and sounded almost bitter. She couldn’t help but compare him and Chuck. Since her simple love never showed up, she was ready to accept Chuck, her great love.

There is only one novel writer in the show who has stimulating conversations with Blair and that person is Dan. She didn’t love Dan back then but right there she was describing Dan. No one can deny that.

In many times through out the show I felt they have described the right person for Blair, the one she was dying to meet and fall in love with. She wanted that knight in shining armor to sweep her off her feet. When she has the conversation with Cyrus she tells him that Louis would never understand her dark side or accept it, and Chuck could never see her light side. In an indirect way they were saying the guys were the two polar ends, when all she wanted was someone in the middle, who would accept the dark Blair and adore the light Blair.

Blair just wanted a guy to understand her, someone who would accept all the mistakes she made. Someone who would understand her intellectual side and admire the marvelous woman she is. Someone she who would give her the real, pure and simple love. Someone who wouldn’t play games with her. Someone who would make her better and respect herself. She wanted happiness. She wanted a love that was worth writing a sonnet and novels about. She wanted a guy who she was willing to kiss, not because she wanted to get back at Chuck or move on from Chuck. She wanted to kiss a guy for her, because she loved him and because she wanted to. Even when she went to Paris she was waiting for him. She wasn’t hooking up with every guy like Serena. She was waiting for this guy. She wanted that guy who would understand what she feels, the person who would understand exactly why she comes alive while reading a book, or looking at a painting. Dan hasn’t always been Blair’s romantic interest but this character, her real love, he has been in the story for a really really long time. This person wasn’t Chuck. He wasn’t Nate or Louis, but doesn’t this person awfully sound like Dan?

Blair is happy with Dan. When Dan finally established a spot in Blair’s life she was her happiest self. Dorota was even worried that Blair wasn’t fighting or being mean, that she was too happy and she was content. Isn’t that how people are? People are saying Blair is too nice. When your life makes sense to you and you are content, is there a reason for you to go around make other people miserable anymore? Dan understands her better than anyone. He peers into her soul. She was so surprised that Dan loved her for her, because she was so afraid that no one would ever love her for who she was. It’s like in that instance all her anger and resentment toward that person who never showed up faded away. She waited so long for that guy to arrive, and she had thought he never would. She shares those stimulating conversations with him. He sees the light side of her, and he says if it is her, then it can not be awful. This is the same Dan who has seen her at her worst so it’s not like Dan doesn’t know what she has done. She trusts him. Chuck accused Dan and she accused Chuck of trying to snatch away her happiness. But when Dan admitted he did send the video although hurt she forgave him. Because she knows Dan, and that he won’t hurt her. She feels safe with him. He is her home. Blair has always had chuck in her heart, but when she realized the person she waited for so long had finally arrived she was ready to give her heart to him. She didn’t want Chuck to have her heart anymore. This wasn’t like Louis who she made space for in her heart. This was different. This made no sense, yet all the sense in the world because it felt right. Blair is not in a dilemma in 5x17. She doesn’t make a pro and cons list like she did with Chuck and Louis. She just knows her heart belongs to Dan.

People say how did this happen? How can she say she loved chuck more and more everyday and then say her heart belongs to Dan. You forget she has been in love with this person for a while now, she loved him more than she loved Chuck, she just didn’t know who he was. She knew it a long time ago that for this person she would be willing to cast Chuck aside. That’s why she said someday she would kiss him, and it will only be for her. And she finally kissed him.