Though Gossip Girl made a point to revolve around Serena, Blair quickly became the romantic hero when no one was paying attention. Her quest to find true love was the most relatable element of the show and the audience followed her triumphs and heartbreaks.
Despite her faults, she became a fan favorite as she managed to pick herself up despite being let down by her boyfriends and best friends alike. Though she found happiness in the end, her life was complicated because of a severe set of setbacks.
Had A Bad Book Written About Her
Blair’s romantic history veered far and wide. Her most cringe-worthy dalliance was the brief time she was with Dan Humphrey. Dan’s obsession caused him to write a book about the Upper East Side with unsubtle pseudonyms. Everyone knew that Blair and Dan had kissed after reading the book and it threw a wrench in her upcoming marriage to Louis.
Was Always In Serena’s Shadow
Blair’s love for Serena was as strong as her jealousy. A point of contention between them had always been how Serena overshadowed her. This was personified by Nate sleeping with Serena at the Shepherd Wedding.
On multiple occasions, Serena proved that she understood how Blair felt but chose to ignore her. She took over the girls at school and took Blair's place as Queen B. When Eleanor chose Serena over Blair as a model at her company's launch, Serena feigned ignorance even though it was obvious what had happened.
Could Not Admit That Nate Didn’t Love Her
Blair’s quest for love was never easy. Even though Nate slept with Serena while they were together, Blair still tried to make it work. Eleanor encouraged the union, telling Blair that Nate had asked about his family’s diamond ring to give to her.
For Nate’s part, he also tried to make it work at his father’s behest. The Captain wanted things to work out between the teens so his business deal with Eleanor wouldn’t be ruined. But no matter how much Nate and Blair tried to make it work, Nate didn’t love Blair. Finally, Blair made the difficult decision to break up with him.
Her Pact With God
Blair had never been particularly religious until she and Chuck were in a devastating car accident. Blair lost her unborn child and it looked like Chuck wouldn’t make it either.
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At the time, Blair had been considering leaving Louis for Chuck. With Chuck's life on the line, she prayed that if Chuck survived, she would go through her impending marriage. Immediately Chuck made a miraculous recovery. Blair decided to follow through with her vow and forced herself into a loveless marriage.
Her Father’s Ambivalence
Blair always had affection for her father. But this was severely impacted after Harold left her mother for Roman, a male model. Blair tried to keep in contact, but Harold never put in much effort after he moved to Paris. Harold loved Blair adamantly but when it came to conflict, he always shied away. He let Eleanor tell Blair that they were officially getting divorced at Thanksgiving. Most of Harold’s parenting was done offscreen.
Postponed A Relationship With Chuck
There were many times that Chuck and Blair decided they couldn’t be together. Sometimes that was not a mutual decision, but the saddest times were when it was. It seemed that Chuck and Blair were always a case of bad timing.
They had made amends following the Jenny debacle and wanted to get back together. But Blair’s ambitions made being with Chuck impossible. They chose to work on themselves before they would work on their relationship. This even carried into the final season. They knew they wanted to get married but had to wait until they sorted their respective lives out.
Had To Pay A Dowry To Get Out Of A Loveless Marriage
Blair’s marriage to Louis was short-lived and not affectionate. From the moment they said their vows, neither Louis nor Blair wanted to be together. The Grimaldi’s true nature came out and even though it was a marriage in name only, Louis refused to grant Blair a divorce.
The Grimaldis demanded that she pay an outrageous dowry, to which fans and characters were all outraged about. Blair was going to be forced to live in a loveless life until Chuck paid the dowry.
Tried To Stick With Chuck Through Anything
Chuck and Blair’s relationship had been intense and dangerous. Blair promised she would stand by him through anything because of her feelings for him. But try as she might, Blair could not stand by Chuck when he traded her to Jack for ownership of his hotel. Chuck was certain that they would get through it, not really understanding how toxic and degrading his decision truly was. This was Blair’s ultimate heartbreak and proved difficult to come back from.
Her Eating Disorder
Lost and alone, Blair's eating disorder was revealed in season one after her father failed to show up for Thanksgiving. Blair’s need for control and lack of support led her to her issues with eating. She was largely ignored by her family and Serena was the only one who was there to comfort her. Though it was generally glossed over afterward, Blair's struggle was heartbreaking and should not be discounted.
Marrying Someone She Didn’t Love
It seemed that Blair would be getting her happy ending when Louis proposed to her. She would get her fairy tale wedding, something she always strived for. It was a great irony that marrying Louis would not make her happy at all. Chuck thought that letting her go would be the best thing for her but he was the one she loved the most.
Blair forced herself to marry Louis because she thought it was in Chuck’s best interest. It broke her heart to tell Chuck that she loved him but couldn’t be with him again.