Gossip Girl: Why Dan and Blair Should've Ended Up Together

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It's been eight years since Gossip Girl aired its final episode, yet the series remains a staple in teen drama history. 

Chuck and Blair's wedding was an event that gave fans a satisfying conclusion to the show's central love story, but was Chair's ending a negative result of its time period?

Truth be told, a relationship such as their's likely wouldn't be 'shipped in today's society. Especially not when the one between Dan and Blair was its polar opposite. 

While Chuck and Blair's romance was built on toxicity and abuse, Dan and Blair were each other's best friend and equal. 

Blair and Dan Image

There's no shortage of horrible things Chuck has done to Blair and in general. But, this is Gossip Girl, and it's difficult to find even one character who wasn't corrupt in some way. 

In hindsight, they were all horrible people. 

However, Chuck Bass' actions, particularly in regards to the woman he claimed to love, was above and beyond what can be deemed as fictional fun. Once you have a main character attempt to rape two different girls in the very first episode, there's no possible way to redeem them. 

There's a difference between setting a character up for a redemption arc, and making them so evil that any type of development gives you an icky feeling. 


This isn't The Vampire Diaries, and the characters aren't supernatural creatures who maim and kill each other over the slightest discrepancy. Gossip Girl is rooted in reality, and the relationships they portray are meant to be a reflection of our everyday lives. 

It was the reality of Chuck and Blair's issues, and the real-life horror stories wrapped into Chuck's character that made their relationship especially disturbing to see deemed as true love. 

The manipulation on Chuck's end made us want to get Blair as far away from that man as possible. Not only did he trade his girlfriend's body to his sleazy uncle in exchange for his hotel, but he tried to make her believe it was her own idea. 

Chuck: I can't let my feelings cost me all that I've built.
Blair: Even if it means losing me, instead? All I ever did was love you.
Chuck: The worst thing I ever did. The darkest thought I ever had. You said you would stand by me through anything. This, Blair, is anything.
Blair: I never thought that the worst thing you would ever do would be to me.
Chuck: You went up there on your own.

It's hard to imagine how a relationship, in which one party sells the other, could ever be something to root for. 

chair 1

Sadly, the abuse doesn't stop there and even gets physical later in the series.

The most important thing to note is that while Chuck would treat Blair one way, Dan would treat her the complete opposite.

It was almost as if Gossip Girl was trying to distinguish between a healthy relationship and an abusive one, which makes Chuck and Blair ending up together all the more puzzling.

After finding out that Blair was engaged, Chuck gets drunk and has a violent outburst that leaves Blair injured and running from his apartment. 

chair 2

Similarly to the hotel incident, Chuck treats Blair like property claiming that she is "his."

Chuck: You'll never marry anyone else. You're mine.
Blair: I wanted to be. I wanted it so badly, but not anymore.
Chuck: You're mine, Blair!

However, when it comes to Dan's feelings for Blair, he handles them differently. Although he too wishes he could be with Blair, he respects that she doesn't have the same feelings for him, and encourages her to find the love she deserves.

Blair, your prince is out there waiting for you. It might not be me or Chuck, but he's out there.


Dan was Blair's support system, her confidant, and her best friend. She even came to rely on him more than Serena as she knew that Dan would be there for her no matter what. 

Dan and Blair's evolution from enemies to begrudging allies to best friends was hands down the most incredible arc on the entire show. 

dair 2

Although the two came from two separate worlds, they slowly but surely realized just how similar they truly were.

They both dealt with their own internal struggles.

Blair was always afraid that she wasn't good enough and that she would constantly be overshadowed by Serena.

Dan, on the other hand, seemed to think he was better than everyone else because he hadn't been corrupted by wealth. But the two managed to balance each other out, and they even became borderline honorable people when they were together. 

And that's saying a lot.

dair 4

Dan and Blair's interactions felt like they didn't belong in a show as dark and deceitful as Gossip Girl.

Their bickering was straight out of a rom-com, and it was disappointing to return to the show's brooding atmosphere when they weren't onscreen together. 

The worst part about it all was that when Blair was with Chuck, she couldn't be herself. Blair Waldorf's confidence was one of the many things that made her so spectacular. 

Yet, when she was with Chuck, Blair always faded into the background. 

blair waldorf

In a moment of honesty, Blair admitted to her mom how being around Chuck made her feel.

What I want is to be a powerful woman. But whenever Chuck’s around I just feel like a weak little girl.


Which is extremely telling when you compare it to what Blair had to say about being around Dan. 

Dan is my best friend and when we're together it's great. I feel strong and safe.


From Blair's verbal acknowledgments of her relationship with Chuck, it's clear that the Gossip Girl writers knew the kind of romance they were writing. So why would they continue to write it?

It almost seems like they were too worried to back out of their original plan. Dan and Blair were ahead of their time, and the teen drama wasn't read to shove aside the toxic relationship they spent years creating. Especially when viewers all across the country were invested in them. 

chair 3

Because we were all more willing to let characters such as Chuck Bass slide back in the day, Dan and Blair were tossed aside and labeled as an obstacle in Chair's journey. 

If a healthy relationship was simply an obstacle for Blair to return to her abusive one, then what kind of message is that sending?

Dan always believed in Blair, even when she didn't believe in herself. He supported her no matter who she wanted to be with, and he loved her for who she was. 

While Blair's strength and independence was an issue for Chuck, these qualities were only a few of the many things Dan admired about her.

dair 3

She never had to dumb herself down to please him, and the two even had lively debates about art and culture. Blair was more herself around Dan than anyone else. 

Blair: Somehow between being traded for a hotel and selling out for a tiara I lost my true self. But I want to be found. Could you possibly help?
Dan: I have a feeling that the real Blair Waldorf is a lot closer than you think. It wasn’t all that long ago that she and I were working side-by-side at W. And I totally fell for her.
Blair: And what was that girl like?
Dan: That girl is fiercely strong. Independent. Outspoken. Beautiful. Capable of anything. And no man or magazine should be able to take that away from her.

Their romance could've been the one that broke the mold for all the teen dramas to follow. 

The world just wasn't ready for a Humphry-Waldorf relationship. But, it is 2020 and a Gossip Girl reboot is in the works. 

Gossip Girl writers, if you wanted to change your mind about Dan and Blair's relationship, you have the perfect opportunity. 

Anything is possible, right?

What do you think, Gossip Girl fanatics?

Do you think Dan and Blair should've ended up together? Or are you still Team Chair all the way?

Let us know in the comments section down below! 

And don't forget, if you haven't seen the show you can watch Gossip Girl online right here at TV Fanatic.

Rachel Foertsch is a staff writer for TV Fanatic. Follow her on Twitter.

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