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All Of Blair Waldorf's Relationships In "Gossip Girl" Ranked

Was Chuck Bass actually the one for her? Was Louis actually such a bad person? Was it actually awful for Chuck to trade her for a hotel?

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6. Chuck Bass

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Did you really think anyone else would earn the number one spot? Chuck Bass and Blair Waldorf were meant to be together from the first episode, and there is absolutely no denying it. Chuck and Blair's manipulative personalities fit together like pieces in a puzzle. No matter how many times they broke up or found themselves in disastrous situations that most couples could hardly imagine, they always returned back to each other, whether it took minutes, days, weeks, or months. There could be no person better suited for Blair than the wonderful, albeit frustrating, Chuck Bass.

5. Dan Humphrey

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Dan and Blair both have a soft side, which made their romance work. He was her comfort in a time of need, the problem being that Blair is a strong independent woman, making it impossible for Dan to keep her forever. His role as her knight in shining armor is the one and only reason he earned the number two spot on this list. Without Dan, who knows, Blair might still be stuck with Louis.

4. Nate Archibald

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Prom king and queen who had been dating since they were kids and were planning on getting married before they were twenty years old is a storyline that is much overused. As perfect as their relationship seemed, it was just that which made it too perfect for it to last. Nate's laid-back personality is no match for Blair's mischievous self.

3. Louis Grimaldi

Gossip Girl, The CW

Nothing about Louis and Blair's relationship looked like it was going to work out in the end. Everyone knew that she was still in love with Chuck, and it was obvious that they were both struggling to love each other. Louis had to face the fact that Blair had feedings for someone else, no matter how hard she tried to hide them, and Blair had to suppress her feelings for Chuck to keep her promise to God and get the fairy tale ending that she had always dreamed of. When Blair confessed her feelings for Chuck at the wedding and was then told that she would be Louis' wife for show the relationship was doomed. The only thing that keeps this couple from earning the lowest spot on this list is that the relationship started out very strong.

2. Lord Marcus Beaton

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There were a lot of problems with this relationship, on both sides. Lets start with the fact that he was having an affair with his step-mother, who was having an affair with Blair's ex-boyfriend and friend, Nate, at the same time, while she was also married. And if that didn't complicate this enough, Blair didn't even want to be with Marcus (who she knew as James at first) until she found out he was a Lord. And, to finish it all off, the only reason she started seeing James (who she later found out was Marcus) in the first place was to make Chuck jealous. This relationship was disastrous from start to finish.

1. Jack Bass

Gossip Girl, The CW / Via

And one night stand in exchange for your boyfriend's hotel isn't the best way to begin a relationship anyways. Add in the fact that the person you're sleeping with is your boyfriend's uncle and you get the disastrous relationship that was Jack Bass and Blair. Ultimately, Jack somewhat makes up for this by helping out Blair and Chuck in season 6 when they need it most, but it was still a pretty trashy thing to do, and absolutely nothing good came out of this.

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