On the Upper East Side, there was not a more epic tale of romance than that between Blair Waldorf and Chuck Bass. In the world of Gossip Girl, they alternately tried to make one another miserable and be one another’s happy ending. Their relationship was a roller coaster, and one fans wanted to root for even when it was turned upside down.
Just because Chuck and Blair kept finding their way back to one another doesn’t mean they were actually the best match for one another. There are quite a few other characters that could have made better matches for Blair if they’d wound up together.
Nate
Nate has a reputation as one of the most boring members of the “nonjudgmental breakfast club,” but the truth is he could be just as underhanded as the others. In fact, his scheming was often employed by Blair to get back at other members of their circle, or to protect them.
Nate and Blair tried a few times to make a relationship work, but they always seemed to wind up hurting one another. If they had waited until they were adults and had gone through some of their growing pains, they might have found themselves much better suited to one another.
Scott
Scott Rosson probably isn’t a character many fans remember. He only appeared in a handful of episodes and Blair didn’t even interact with him that much. He was the son of Lily and Rufus from their teenage days.
Though Scott’s final episode maintained that he wanted to get to know the members of his birth family, he never appeared again. He had his half-siblings’ taste in books and art (Dan) and the ability to scheme (Serena). Scott could have provided Blair with the best parts of the people she was closest to, making an interesting match for her.
Georgina
Georgina was often described by fans of the series as a female version of Chuck. She was a schemer who wanted to control everything around her. That led to her never really trusting anyone and no one trusting her.
Despite her questionable morals, Georgina was smart, strong, and formidable - everything Blair admired in the women in her life. If Blair ever entertained the idea of being with a woman, she and Georgina would have made quite the power couple and ruled the Upper East Side.
Carter
Like Georgina, Carter had a lot in common with Chuck. The only difference was that Carter repeatedly tried to take responsibility for his actions only for someone else to come and bail him out. He messed up his chances with Serena, but Blair was someone who could appreciate his attempts to be the one in control.
Would Carter and Blair have been able to maintain a lasting relationship? With a little bit of work, sure. It would have been a bumpy road, just like her relationship was with Chuck. Carter, however, was well on his way to becoming a better person long before Chuck.
Raina
Most of Raina and Blair’s interactions centered around, as even most casual fans could guess, Chuck. Like Blair, Raina dated both Chuck and Nate before deciding to leave New York for her hometown of Chicago.
Raina was a smart businesswoman who valued family connections - something Blair could understand. The two had a lot in common and could have benefitted from spending some quality time together. A life outside of New York could have just been just what Blair needed as well.
Jack
A controversial pick for Blair would be Jack Bass. Chuck’s uncle was not a good guy, but Blair proved more often than not that she actually liked the guys with questionable ethics.
Blair and Jack had a brief dalliance, but he was more often known as the guy Chuck tried to give Blair to in exchange for getting a hotel. When it came to Jack, Blair knew exactly what she was getting. He might have been a bad guy, but he didn’t actually manipulate her into thinking he was a good guy. He would have brought out the worst in Blair, but it certainly could have been fun to watch.
Someone Dorota Set Her Up With
Other than her best friend, there’s one person on the series who truly knew Blair better than anyone. That’s Dorota. She began the series as a member of the Waldorf’s household staff but became one of Blair’s most trusted confidantes.
Dorota always had Blair’s best interests at heart. She would be the one person who would set Blair up with someone who didn’t just have a spark, but would actually be good for her.
Serena
Serena and Blair had a rocky past. They were best friends, but the power struggle between them meant one of them always wanted to be considered the prettiest and most popular of all. That competitive nature slowly fizzled as they matured on the series, and they became much more supportive of one another by the time the finale rolled around.
Who better to start a romantic relationship with than someone who knows you better than anyone else? The two women could have left behind the guys in their lives that made everything difficult. Chuck and Dan were still holding onto their secrets right up until the end of the show whereas Blair and Serena had already agreed not to keep things from one another anymore.
Dan
Watching Dan and Blair gradually become friends over the course of the series was definitely a highlight of the show. The two were more alike than they thought with similar interests in art, movies, career paths, and even food. Blair and Dan could debate something other than sexual politics and actually learned something from one another. It’s a shame they went back to Chuck and Serena in the end.
It’s a little bit harder to make this argument in light of Dan’s reveal as Gossip Girl in the series finale, but Dan and Blair were actually a good match while they lasted. If only he hadn’t been the guy behind the girl revealing all of the Upper East Side’s secrets.
Someone Who Has Never Heard Of Gossip Girl
To be perfectly honest, all of the main characters could have benefited from a fresh start at the end of the series. Despite so many fans wanting to see the core four paired up, their lives were defined by Gossip Girl and their relationships with one another for so long that someone completely new would have been their best option.
Getting away from the traumas of their teenage years and allowing themselves to grow would have been best. Blair especially had a tough time in the Upper East Side as Gossip Girl tracked her every move and exposed every relationship secret she had. She would have been better off starting over with someone completely unconnected to everything that had transpired from the moment the online voice entered her life.